The Big “What If”: Rask for Raycroft, Part II


It’s funny how real life works out, sometimes. Tuukka Rask, once upon a time a draft pick of the Maple Leafs, is facing the team for the second time in the post-season (the first being in 2013). For Toronto, it’s only their third playoff appearance since the 2004-05 lockout; more often than not, when they get to April hockey, they’ve had to face the goalie they once drafted, and then traded away.

This is the second of two parts to the Rask-for-Raycroft series. If you haven’t viewed the first part, or would like to do so again, please check it out here.




June 24th, 2006


The Toronto Maple Leafs’ draft table is a busy one.

As the 2006 NHL Entry Draft begins, John Ferguson Jr. is dealing with more than one issue. Firstly, of immediate importance, there is the question of who to draft with their 13th Overall Pick. According to the International Scouting Service, Bryan Little was the young man expected to go at that spot, but whenever the chance came to grab a good young centreman, teams were bound to drop a bit in the rankings to get them. Maybe they could grab a hard-nosed winger like Chris Stewart, who had just finished a breakout season with the OHL’s Kingston Frontenacs. Or maybe they could grab someone they had looked at in Europe, possibly someone like Michael Frolik or Jiri Tlusty. They had some good choices available, and quite a bit of thinking to do.

Another area of concern, however, was in their eventual goaltending vacancy. The previous season had finished with 40-year-old Ed Belfour showing himself to no longer be capable of being a top NHL starter. His goals against average was a poor 3.29, and his save percentage was .892, .007 below league average – a number that looks even worse for a #1 netminder. Mikael Tellqvist wasn’t much better, but he was expected to be a back-up, anyway. Jean-Sebastien Aubin had filled in admirably late in the season, earning himself a 9-0-2 record in 11 games; his play late in the campaign nearly dragged Toronto into the playoffs. But as good as he had been that year, it was in a short run. He hadn’t been a starter since the 99-00 season, a year in which he performed well, only to lose his form (and his starting job) the next year.

The mission objective for JFJ was the playoffs. The Maple Leafs had spent the first part of the decade as a constant post-season presence, making a run to the Conference Finals in 2002. Maple Leaf Sports & Entertainment had not missed out on the playoffs since their rebranding after the 97-98 season, and likely did not want to miss out on playoff revenues. And, of course, there was the chance to play for a Stanley Cup to think about. It may not have been much of a chance, but even an 8th seed could make it all the way to the Final; just ask Edmonton, who got to Game Seven against Carolina from the last spot in the Western Conference.

In short, playoffs were the goal, and in order to secure that goal, they needed a capable starting goalie. Their draft pick comes and goes; with players like Bryan Little, Michael Frolik, and James Sheppard unavailable to them, the Leafs use their pick on Czech prospect Jiri Tlusty, a young forward out of Kladno. Now, their focus is on making a move to get a goalie, and the thinking begins. Their first target of interest for a potential deal is the Boston Bruins, who have three goalies at the NHL level. The first is Tim Thomas, who just came over from Finland for a second stint with Boston. At 31, he managed to grab the starting role late with some good performances. The second is Hannu Toivonen, a rookie who was pencilled in as the back-up, and performed well in that role. Seen as a future starter, it would be tough to pry him out of Boston’s hands. The third is Andrew Raycroft, a former Calder Trophy winner in 03-04, who looked to be their starter for this year, but lost his job thanks to poor play. If a team had goalie depth to spare, it was them.

John Ferguson Jr. heads over to the Boston table, looking to talk to new Bruins GM Peter Chiarelli. The two move aside to discuss the deal, and Chiarelli says that Thomas and Toivonen are off-limits. They might be willing to give up Raycroft, but the price would be steep. The Maple Leafs have two goalie prospects to give up, and if Boston was to give up their former Calder Trophy winner, one of either Justin Pogge or Tuukka Rask would have to go the other way. Ferguson decides to confer with his scouting staff, as well as his new head coach, Paul Maurice. The discussion seems to be centred on whether they would give up Pogge, who had just won the 2006 World Juniors with Canada, or Rask, who was named the top goalie by both the media and the directorate at that same tournament. The consensus seems to be the Pogge, seen as more NHL-ready, would be the guy to keep going forward.

Just before Ferguson goes back to further negotiate the trade, one of his assistants stops him, and informs him of Raycroft’s contract situation. The Boston goalie is headed to free agency, and it was uncertain whether the Bruins would offer him a deal at all – making him unrestricted, and a free target for signing on July 1st. Armed with this info, Ferguson indeed heads back to talk with Peter Chiarelli, but this time, to inform him that the deal is off. Toronto must now look elsewhere for their new starting goaltender.




WHAT MUST CHANGE: As previously mentioned, the Maple Leafs would have to consider that Raycroft was no longer a viable trade option, either for a perceived lack of talent, or due to his contract situation. But their needs wouldn’t change, just their target. And their desperation to find a new goalie wouldn’t change, either. This was, after all, a team that had just missed the playoffs in a city where playoffs were seen as a given in recent years.

So, with all this in mind, if not Andrew Raycroft, then who?

Certain points must be considered for what I would consider a likely trade target in this case:

  • The goalie the Leafs acquire must be somewhat young, possibly between 24-28 years of age at the time of the trade. They had just given up on a 40-year-old Ed Belfour, and likely wanted somebody they could rely upon long-term, and not simply a stop-gap. (I have chosen that age range based on the age of Raycroft at the time of the deal.)
  • The goalie they acquire has to be someone with previous starting experience (defining “starter” here as >41 games in a season), with a save percentage of over .900 in that year. In the case of Raycroft, he had played in 57 games in his rookie year, and performed very well, winning the Calder Trophy with a 29-18-9 record and a .926 SV%.
  • The goalie they acquire must have regular playing time, but not quite starting time (between 25 and 40 games in the 05-06 season). Teams were not going to be giving up a starter unless they felt that they had somebody else who could play just as much as the netminder they are parting with.
  • The goalie they acquire must, in my view, have a save percentage below .900 in the 05-06 season. Anyone above average in the SV% department would likely be more sought-after, and thus the price would go beyond Rask alone. If Rask is the only piece given up, they’re not going to get a top goalie.

In comparing goalies across the league to Raycroft, I found that only a few matched even half of the criteria I listed, and nobody matched all four. Raycroft was unique in that he had previous starting experience; anyone else who did had earned their starting time in the 05-06 season, not prior to it. And of those that were starters, the list in the ages I mentioned included the like of Henrik Lundqvist, Roberto Luongo, and Rick DiPietro – names that nobody in their right mind at the time would trade for a goalie prospect who was still a few years away from becoming an NHL regular.

John Ferguson Jr. finds himself in a bind. He now needs to act quickly if he wants to get somebody to be Belfour’s replacement. He converses with General Managers all across the floor of General Motors Place, looking for a deal to be made. Chatter starts to rise among media members, with several reporters being alerted to the possibility of a trade by the Leafs on Draft Day. Eventually, Ferguson finds a GM willing to take a break from the business he was conducting to talk a trade, and a deal is soon agreed to. The two head to the league’s desk to make the trade official, and Gary Bettman heads up to the podium on the draft stage to make the announcement.

Gary: We have a trade to announce… The Pittsburgh Penguins trade Sebastien Caron to the Toronto Maple Leafs, in exchange for the rights to Tuukka Rask.

It signalled Toronto’s desperation to find a goalie in that moment that they were willing to trade a top goaltending prospect for Sebastien Caron, who had performed poorly that year in front of an awful Pittsburgh team. In an interview with James Duthie on TSN, John Ferguson Jr. stated that he wanted somebody with regular NHL experience; the other candidates he had looked to in the NHL were either too inexperienced, or cost too much to acquire. JFJ also spoke to the good situation his team had in terms of goalie prospects, as he had the choice of either Tuukka Rask or Justin Pogge to keep for development. Indeed, trading Pogge would seem like professional suicide for Ferguson, considering that not only did Pogge win the 2006 World Juniors in British Columbia, he was also raised in the province (specifically, in Penticton). Trading a local boy at the Draft would turn almost all of the team’s many Western-based fans against him, and possibly even put his job at risk.

From Toronto’s Perspective: At first, there would be serious concern from both fans and media alike at the fact that Toronto traded a highly-regarded prospect for someone who had not performed well the previous year. More optimistic sections of the Maple Leaf fan base would try and find the positives in this move, of which there were a few. Firstly, Caron DOES have a good bit of experience in the National Hockey League, 90 games worth. His save percentage the previous year was a dreadful .881, but he was still behind a defense that allowed the 4th-most shots in the NHL that year. With Toronto having somewhat better defending (only to get better in a few days with the signing of Pavel Kubina and Hal Gill), Caron may not have to be subject to so many scoring chances, and his save rate could improve. And if he didn’t work out so well, at least they still had Justin Pogge for the future.

2006-07 finally comes along, with Sebastian Caron pencilled in as the #1 goalie. Any hopes of Caron finding his 2002-03 form (2.64 GAA, .916 SV%) quickly evaporate as the first few games come along. The poor guy tries hard, but he constantly finds himself out of position on several shots. Despite his clear inadequacy for the starting role, he still finds himself playing the majority of the games out of sheer necessity. The season quickly devolves into a comedy of errors in goal; try as he might, Jean-Sebastien Aubin can’t rescue another season for Toronto, and by February, there is no hope of a playoff berth. Caron’s numbers tell the story: 51 games, with a save percentage of .877, worst in the entire league among starters. John Ferguson Jr. loses his job; his legacy will now be tied to a desperate trade he made to try and get a starting goalie, only for the move to backfire. Though Paul Maurice failed to lead Toronto to the playoffs in his first year, he is given little blame for the failure of his goalies. As the saying goes, “you go to war with the soldiers you have, not the soldiers you want”.

With Ferguson now out, the Maple Leafs go to their history to bring in his replacement. Having been relieved of his position as senior executive VP of hockey relations with Phoenix, Cliff Fletcher was now available for Toronto to sign. Fletcher had previously served as the Leafs’ GM from 1991 to 1997, helping build the competitive Toronto teams of the early part of the decade. He was responsible for one of the most infamous trades in league history, bringing Doug Gilmour in from Calgary in a 10-man deal that gave the Leafs a centrepiece for their strongest seasons since the beginning of the Expansion Era. He was getting up there in years, now in his 70s, but MLSE believe that he is just the guy to bring Toronto back to being a Cup contender.

Fletcher takes over the job in early June, and make a quick impact with his first deal, sending the Leafs’ 1st and 2nd-Round Picks that year, as well as their 4th-Rounder in 2009, to San Jose in exchange for Vesa Toskala and Mark Bell. Toskala had been the back-up for Evgeni Nabokov for the past few years, and put in good efforts when called upon. The belief was that he would come in and serve as a starter without compromising the good numbers he had put up with the Sharks. Toskala comes into the line-up in 07-08, but despite some good efforts, he can’t keep Toronto in every game. Caron, the man who was now relegated to the back-up role, continued to stink whenever he was on the ice. Toronto, by January, were now well out of playoff contention, with little hope for any sort of rise up the table in the late months.

With this in mind, Fletcher goes to the MLSE board, and outlines his plan for a potential rebuild. The board members are immediately doubtful, with the very concept of a “rebuild” seen as something the Maple Leafs fans would not tolerate. Having overseen one such phase (and having been removed from his post in order to prepare for another one), Fletcher could at least make a good effort to convince them that this was what Toronto needed. With some trepidation, MLSE agrees to allow Fletcher his chance to rebuild from scratch, and the GM goes to some key players in the Leafs’ locker room in order to see who would be willing to sacrifice their spot in the locker room for this plan. The player he has to try hardest to convince is captain Mats Sundin; a long-time Leaf, Mats loved it in Toronto, and didn’t feel comfortable with simply being dealt before a playoff run. Fletcher pleads his case… and eventually, Mats relents, agreeing to waive his no-trade clause. Tomas Kaberle, meanwhile, is also dealt out to Philadelphia for Jeff Carter and a 1st-Round Pick in 2008.

To Dallas: Mats Sundin, Sebastien Caron

To Toronto: Mike Smith, Jussi Jokinen, Jeff Halpern, 2009 4th-Round Pick

To Philadelphia: Tomas Kaberle

To Toronto: Jeff Carter, 2008 1st-Round Pick


The Sundin trade listed is almost a mirror of what happened in the OTL, with the Tampa Bay Lightning involved instead of Toronto. The Lightning, struggling in the standings, dealt centreman Brad Richards and backup netminder Johan Holmqvist to the Stars for the package above. The Kaberle trade, meanwhile, is a trade that was actually proposed in real life, only for the defenseman to nix the deal.

Four other picks are acquired at the deadline for Wade Belak, Chad Kilger, and Hal Gill, as Toronto begins a rebuild to try and get themselves some building blocks for the future. Though Sundin does manage to make it to the Conference Finals with the Stars, they are eliminated by Detroit in a hard-fought, seven-game series. Kaberle, too, makes the Conference Finals with Philly, only to lose to the Pittsburgh Penguins. Though Kaberle continues to play with the Flyers, Sundin elects to go to free agency, eventually signing with the Vancouver Canucks in late 2008. Toronto now has two 1st-Round Picks in the 2008 Draft; finishing 4th-last in the league, they use their natural pick on defenseman Alex Pietrangelo, while using their pick from Philly on another D-man, American John Carlson.

2008-09 is supposed to be firmly a rebuilding year, no room for trying to compete. Strangely, however, the Leafs actually put up a good fight in the standings. Jeff Carter has a breakout year as the #1 centreman, managing 84 points in 82 games; his 46 goals is the highest since Mats Sundin hit 41 in 2001-02. Mike Smith, brought in from the Sundin trade, actually manages to be very effective as the season goes on, putting up a .916 SV% in 33 games, and giving Toskala a run for his money. The Maple Leafs, expected to be in the running for John Tavares, instead end up just outside the playoff spots, finishing in 11th with 89 points. Their building of the defense continues at the draft, as they select Ryan Ellis with the 11th pick. (The 4th-Rounder they acquire in the Sundin trade is used on blue-liner Kyle Bigos, who never makes it to the NHL.)

Unfortunately, they now have to make a decision with the goaltending prospect they had tried to nurture these past three years. Justin Pogge was brought to the Toronto Marlies in the 06-07 season, and was expected to develop himself into a capable NHL starter by this point. Though his first two years showed signs of steady improvement, his third showed a goalie that was starting to fall behind. His last season saw him put up a .895 SV%, and his playoff run that year turned out to be disastrous. His few flashes of NHL duty didn’t impress, either, as he started 6 games, 5 of them losses. Incoming Leaf GM Brian Burke decided it was best to end the Pogge experiment, dealing him to Anaheim for a 6th-Round Pick in 2011.

Speaking of Brian Burke, he is brought in at the end of the 2008-09 regular season to replace Cliff Fletcher, who took a step back to act as a senior advisor. Burke wasn’t looking for a rebuild; he wanted a Cup contender, and he was willing to do everything in his power to bring the Leafs to that level. His strong desire to build the team this fast afforded him a degree of autonomy that someone like John Ferguson Jr. didn’t have, and he was allowed to do his job with little interference. His first big trade comes in the 2009 pre-season, as he deals Toronto’s 1st-Rounders in 09 and 10, as well as their 09 2nd-Rounder, for Boston’s RFA forward Phil Kessel. Of course, this is directly what happened in the original timeline, but the circumstances are different. Now, instead of giving Toronto a potential franchise winger to build around, the deal gives them somebody who can link up with Jeff Carter long-term, and put the team over the top.

There is serious excitement in the air in Leafland, as it looks like for the first time in a while, the Buds are ready to make a post-season run. Unfortunately, Burke’s attempt to build for a Cup run ends up backfiring HARD. The team struggles out of the gate, as Kessel waits to return from an injury suffered during an exhibition game. Alex Pietrangelo is rushed onto the NHL roster, and struggles in his first season. Mike Smith, a solid performer the previous year, is dragged down to a .900 SV%, while Vesa Toskala puts up numbers in goal that even Sebastien Caron would cringe at (3.66 GAA and .874 SV% in 26 games). The defensive free agents brought in to aid the likes of Pietrangelo turn out to be far too slow for an evolving game. Even trading Toskala to Anaheim for Jean-Sebastien Giguere isn’t enough to reverse their fortunes; Toronto ends up dead last in the East, earning only 72 points. The 1st-Rounder and 2nd-Rounder they gave up in the Kessel deal are used on Tyler Seguin and Jared Knight, respectively.

The MLSE board is infuriated. They were promised a playoff spot, and Burke delivered the team a last-place finish in the Conference, after the team was so close a year prior. Now the knives are being shown, and Burke is informed that if Toronto doesn’t make the playoffs this time around, he’s toast. Burke sticks to his plan, hoping that the new Smith-Giguere duo will prove fruitful for next year, and that the Carter-Kessel duo will click. Burke turns out to be wrong about the goaltending duo, but is saved thanks to the advent of rookie netminder James Reimer, who gets a few starts in January to prove that he’s ready. He grabs the starting role, and never looks back. And Alex Pietrangelo, after a horrible rookie year, bounces back in a big way, putting up 47 points in 82 games to lead all Toronto blue-liners. His fellow young D-man, John Carlson, also finds his way on to the big squad, and notches 37 points in 82 games. The Leafs manage to make their first playoff appearance in the post-lockout era, matching up against none other than the Boston Bruins. They put up a decent fight, but Boston makes short enough work of the Buds, winning in five games.

Despite the playoff appearance, trouble seemed to be brewing in the locker room. Jeff Carter had been the subject of controversy for some time, now, as rumours had spread about his off-ice habits, with a few articles alleging an apparent drinking problem. Though both Carter and his GM denied it, the rumours only continued to magnify over time, and eventually, Burke felt it was time for the team to move on from him, if only to end the debates once and for all. Carter is dealt just prior to Draft Day, ending up with Columbus. Going the other way were young winger Jakub Voracek, and the Jackets’ 1st and 3rd-Round Picks in the 2011 Entry Draft. Those picks were used, respectively, on Sean Couturier and Nick Cousins.

(Now, I’d like to take this moment to sort out the deals and picks that happen a little bit prior the 2011 Entry Draft, because quite a bit changes in the alternate timeline. Firstly, Toronto’s 1st-Round Pick ends up at #15 thanks to their playoff appearance. Boston, who holds the pick via the Kessel trade, uses it on Nathan Beaulieu. Secondly, because the Kaberle trade has already happened, Toronto does not acquire Joe Colborne, Boston’s 1st-Rounder this year, or their 2nd-Round Pick in 2012. As a result, the Leafs don’t make the trade up the draft order to get Tyler Biggs, and don’t send the other pick to Colorado to get John-Michael Liles. The Percy pick is completely unaffected; Toronto still picks him. And finally, because they never move up to get Biggs, Toronto hold on to their natural 2nd-Round pick, which they use on John Gibson.)

There is hope once again in Toronto. They’ve finally broken their playoff drought, and have the pieces to one day be a serious contender. The 11-12 season has the Leafs running a tandem of James Reimer and rookie Ben Scrivens, a college free agent from a couple of years back. Their defense has been augmented by the development of Alex Pietrangelo and John Carlson, and the addition of Jakub Voracek gives the team a bit of peace and quiet in the locker room, if a bit of a downgrade on the ice. Thanks to their now-superpowered blue line, the Leafs are truly starting to look dangerous. They finish the year with 98 points, good for 7th in the East. Toronto is matched up against the B’s once more, who hold home-ice advantage despite the Leafs having 8 more points. Once again, it is Boston that goes through, this time in a wild five-game series that sees both Reimer and Scrivens utterly shelled in the first two games. (In a cruel twist of fate, Jeff Carter is traded to Los Angeles before the deadline, and the Kings finish the season as Stanley Cup winners.)

Going into the 2012 Entry Draft, Brian Burke was left with a bit of a quandary in regards to his young core. Alex Pietrangelo and John Carlson had proven themselves on the NHL roster, with Jake Gardiner on the way to joining them. Dion Phaneuf, as the team’s captain, was going nowhere. This left Ryan Ellis expendable; Ellis hadn’t played too much over the past two years, but there was still some potential to be realized. Indeed, Ellis would be the one shipped out, going to Philadelphia for former 2nd-Overall pick James van Riemsdyk. JVR was a left winger, a position where Toronto had a need. Try as he might, Jakub Voracek couldn’t quite play alongside Tyler Bozak and Phil Kessel, and they needed someone more familiar with that left side to take that spot. Because of their finish the previous year, Toronto picks 16th in the Entry Draft, selecting Czech forward Tomas Hertl.

Though a lockout threatens the 2012-13 season, the NHL and NHLPA eventually agree on a deal, with play set to begin in January. But for Toronto, a very key face is missing. Under some rather unclear circumstances, Brian Burke is let go by the Leafs, replaced by assistant GM Dave Nonis. Rumours circulate, just as they did in the wake of the Jeff Carter trade, but Burke is extremely retaliatory, going so far as to sue whole websites for anybody in their comment sections even alluding to the popular theories of the true reason of his dismissal. Nonetheless, Toronto pushes on. The addition of van Riemsdyk turns out to be a boon for the Maple Leafs, who finish the shortened season on top of the Northeast with 65 points. Matched up against Ottawa in the first round, the Leafs are confident; after all, each of the past time they’ve faced the Sens in the post-season, Toronto has come out on top. The first round arrives, and Toronto, bolstered by the home-ice advantage, repeats history with a five-game win over their provincial rivals.

Next up, however, is a real treat. For the first time since 1979, the Maple Leafs are to square off against the Montreal Canadiens. The hockey world is on pins and needles (save for most of Western Canada, who quickly become sick to death of even hearing the words ‘Toronto’ or ‘Montreal’). The series turns out to be one of the very best in the history of the NHL. It has everything a fan could want, and more. Want high-octane scoring? You got it, here’s five goals each in the series from Brendan Gallagher and James van Riemsdyk. Want some scintillating saves? Carey Price and James Reimer can deliver those in spades. Want some bad blood? The line brawls of Games 4 and 6 have you covered. The series goes to a decisive seventh game, with Toronto erasing a 3-1 deficit thanks to two straight wins. And just to up the drama, Game 7 goes to overtime. A brilliant penalty kill on a five-minute major by Colton Orr is not enough to deny the Habs forever, as Erik Cole scores at 7:04 of the 1st OT – his third of the game, and the final dagger to Toronto’s season.

For Leaf fans, it is total heartbreak, and for Hab fans, it’s a victory that will be held over their long-time rivals for generations. But for the hockey world, it’s a shining moment that erases the pain of yet another lockout. Despite conventional wisdom saying otherwise, TVs in the United States watch the Leafs-Habs series more than any other match-up in that round. Amazingly, even this series would be topped; the next round saw the Canadiens matched up against the Pittsburgh Penguins, with the Pens managing to do the unthinkable, and come back from a 3-0 series deficit to move on to the Stanley Cup Final. The icing on the cake was the fact that Marc-Andre Fleury was relieved of his starting duty after Game 3, with none other than Tuukka Rask taking over.

For Toronto, it’s a sign of progress, but they still have concerns to address in their line-up. In particular is the play of their goaltenders in the playoffs, as James Reimer has been pulled in four starts in two years. Ben Scrivens isn’t much better, not managing a single win. Dave Nonis feels the need to make a move at this point, and finds a willing partner in Los Angeles. To the Kings go their 2nd-Round Pick in 2015, Ben Scrivens, and Matt Frattin, and to the Maple Leafs goes goalie Jonathan Bernier. Bernier was a highly-touted prospect in the L.A. system since his drafting in 2005, but he was stuck behind Jonathan Quick, who had become a true elite NHL starter. Bernier would likely form a 1A-1B tandem with Reimer, with the hope that Bernier could give the team more cover in the event that Reimer falters in the post-season. At the Draft itself, the Maple Leafs, picking 25th in the 1st-Round, select winger Michael McCarron.

2013-14 begins with Toronto now picked for a Stanley Cup run. They have tons of scoring talent, a deep defense, and a solid goalie tandem that can stand up to just about anybody in the league. The emergence of Tomas Hertl gives the Leafs yet another offensive weapon, and an unexpected fan favourite; his love of Dave & Buster’s becomes somewhat memetic in the hockey world, especially among Leaf fans, who make pilgrimages to the D&B’s just north of the city hoping maybe to meet him there. With an energetic locker room, an impressive Bernier, and a fantastic season by Pietrangelo, the Leafs finish second in the new Atlantic Division with 106 points, matched up against Tampa Bay in the first round. Bernier plays well as the starter, but Ben Bishop is even better in goal for the Lightning, who easily beat the Maple Leafs in five games. (Picking 19th in the Entry Draft, Toronto selects Anthony DeAngelo, a controversial but talented D-man from the OHL’s Sarnia Sting.)

Going into the 2014-15 season, there is now pressure mounting on GM Dave Nonis and head coach Ron Wilson to make a good run in the playoffs. They have begun to take a step back, being eliminated in the first round again, and the MLSE board is getting less patient. Former NHL star Brendan Shanahan has been brought in as team president, and gives the two an ultimatum: Progress in the playoffs, or lose your jobs. Things get dicey for the Leafs as James Reimer gets injured during the season, but his replacement, rookie John Gibson, does pretty well in his stead. Gibson makes 21 starts, and posts a 13-8 record, with a save percentage of .914. Despite Gibson’s emergence, and the All-Star play of Jakub Voracek, Toronto barely misses out on a playoff spot, about six points out. For the first time since the 2009-10 season, the Maple Leafs are forced to watch the playoffs from their own homes, rather than being directly involved.

Shanahan makes good on his ultimatum; Dave Nonis is dismissed, as is Ron Wilson, who had been in charge since 2008-09. Their ideas kept Toronto a playoff team, but now that the Leafs were out of the picture, if even for a year, they are now no longer useful going forward. Shanahan instructs scouting head Mark Hunter to temporarily take over GM duties, backed by young assistant Kyle Dubas. Hunter would stay on as head of scouting following the draft, but his replacement would be none other than former Stanley Cup-winning GM Lou Lamoriello, formerly of New Jersey. Wilson’s replacement was also of the highest calibre: former Detroit bench boss Mike Babcock. Babcock, a Stanley Cup and double Olympic Gold winner, gets the highest coaching salary in NHL history from Toronto, who had to compete with Buffalo for his signature.

Shanahan’s plan here is not quite the same as in the OTL, in which he went to MLSE and stressed the need for a full rebuild. This time, he opts for a retooling of sorts, hoping to make the Leafs a Cup contender in little time. After all, the pieces are there, with the likes of Pietrangelo, Carlson, Gardiner, and Phaneuf on the blue line, and a formidable first line of van Riemsdyk, Bozak, and Voracek. John Gibson, who had just been called up for 20 or so games, looked pretty good in his time at the NHL level. With this in mind, the plan was to let this year be a write-off for the new front-office team, and prepare for a playoff run in 2016-17. As a result of their plans, two key names are shuffled out, as James Reimer and Phil Kessel both get dealt – Reimer on Draft Day to San Jose, and Phil Kessel on July 2nd in a massive deal that sees picks and prospects (including young winger Kasperi Kapanen) going to Toronto. On Draft Day, the Leafs pick 12th Overall in the first round, picking up young winger Denis Guryanov.

2015-16 is planned to be a slight rebuild. Without their former starter in Reimer, and a consistent scorer in Kessel, coach Babcock is just trying to get a feel for his new team. As it turns out, the Leafs make it quite a battle in the Atlantic, only to fall just short in the Eastern playoff race by four points. John Gibson serves well as a backup to Bernier, who continues to regress in his starting role. Tomas Hertl slots himself into a #2 centreman role, picking up 21 goals and 46 points in a full slate of games. Despite the hopes for the future, the playoffs end up delivering a painful 1-2 punch to the gut of Leaf fans, as both Phil Kessel and James Reimer end up in the Stanley Cup Final. Kessel, the subject of many a debate (and a scathing article involving an alleged taste for hot dogs), finds a home on a line with Carl Hagelin and Nick Bonino, and actually ends up leading the league in playoff scoring. Reimer, meanwhile, has several outstanding performances in goal to give the Sharks their first-ever berth in the Final. In the end, it would be Kessel and the Pens that prevailed in six games; the man who was run out of Toronto was now welcomed with open arms by the Penguins. (Incidentally, Tuukka Rask also gets a Stanley Cup ring, but due to an injury he suffered early on in the playoffs, it is backup Matt Murray that wins the Pens the Cup.)

The Maple Leafs continue the rebuild prior to the 2016 Entry Draft. This time, the feeling is that Jonathan Bernier is no longer needed as a starter, with John Gibson ready to take the reins. Bernier is traded to Anaheim for a 1st-Round Pick in 2016. Fans in Anaheim are left stunned, as the team has just paid a premium for a goalie who is, at best, a 1B. Toronto now has the 13th, 14th, 25th, and 30th picks in the 1st Round, used respectively on Jake Bean, Charlie McAvoy, Max Jones, and Sam Steel. (They hold on to the 30th pick due to not making the Andersen deal in this timeline.) Also acquired by Toronto is the Coyotes’ 2nd-Round Pick in this draft, sent to the Leafs for Anthony DeAngelo. The pick is used on Libor Hajek, a young blue-liner from the Czech Republic.

The outstanding quartet of prospects means that the Maple Leafs now no longer have to be in a rebuilding mode. With their future secure, the Leafs can make use of their solid talent on the NHL roster to begin a push for the playoffs. Unfortunately, despite a fantastic first season for John Gibson as a starter (.924 SV% in 66 games), the Leafs suffer major setbacks. Tomas Hertl, their #2 centreman, is injured halfway through the season, and is knocked out of the line-up. Sean Couturier, despite his skill, can’t fill the void left by Hertl. The Maple Leafs, in the end, finish just outside the playoffs once again, 10th in the East with 90 points. Their taste for drafting defensemen continues this year, as they pick Cal Foote with the #13 pick.

The Maple Leafs Today: In the past few years, there have been some struggles, but there is still a feeling of optimism among Leaf fans. The line-up looks pretty impressive on paper, especially the defensive core; the quartet of Alex Pietrangelo, John Carlson, Jake Gardiner, and Nikita Zaitsev is one of the best in the NHL, and that’s with the likes of Travis Dermott, Charlie McAvoy, Jake Bean, and Callan Foote yet to make it. (Pay attention to Dermott and McAvoy, who could be challenging for roster spots right out of training camp.) In goal, the Leafs look set with John Gibson as their starter, who had a very respectable first season in that role in 16-17. His backup going into this year is Curtis McElhinney, claimed on waivers from Columbus the previous season. McElhinney did very well in his short time with the Leafs, and is well regarded as a great locker room presence. Up front, Toronto has some questions to answer, especially down the middle. Tyler Bozak isn’t exactly a #1 guy, and his deputy, Tomas Hertl, is running into injury issues. Sean Couturier has never really had that breakout season, but the management team seems to be convinced that he has the stuff to one day take the job from Bozak. (Some have even said that this upcoming season will be the one where he makes his ascension.)

All in all, the Maple Leafs aren’t a Cup contender, but they are at least competitive. And any worries for the future were certainly alleviated by their fantastic 2016 Draft, which saw Toronto grab SEVEN players in the first two rounds. Even though a few contracts (particularly James van Riemsdyk, Tyler Bozak, Leo Komarov, and John Carlson) look to be expiring, the Leafs will have the salary room to replace them, and could do well in promoting their own prospects like Denis Guryanov or Andreas Johnsson. If everything goes right for the Leafs, they could make a Cup run, and if everything goes badly, they at least have enough in their cupboard to prepare for the future.

Despite the talent they have, Toronto has become somewhat of a hard place to play. For a period of time under Ron Wilson, the Leafs were a regular playoff presence, but it seemed like every time they got to the post-season, their nerves were tested beyond their breaking points. The Wilson-era Leafs won only one playoff series, and not only was it in the lockout-shortened season, it was against Ottawa – a team that they have never lost to in post-season play. And in addition to the playoff struggles, Toronto now has a reputation of being a city that players either can’t play in, or can’t wait to get away from. Jeff Carter was brought in to be the #1 centreman, and left amidst a litany of rumours about his drinking issues. Phil Kessel, too, found himself on the outs, criticized endlessly by the Toronto media for his perceived laziness. Both Carter and Kessel ended up winning the Stanley Cup in their first season outside of Toronto, with James Reimer almost doing the same (only to be stopped by Kessel’s Pens in 2016). Team President Brendan Shanahan is trying his best to make Toronto an attractive place to play, and adding the likes of Lou Lamoriello and Mike Babcock certainly won’t hurt.

But let’s cast our attention to the trade that took place so many years ago: the infamous “Rask-for-Caron” trade. It was a desperate move by a GM with little autonomy, and John Ferguson Jr. paid the price for it with his sacking in May 2007. Oddly enough, it may well have been the catalyst for the Leafs’ success later on, thanks to Cliff Fletcher being hired following the 06-07 season, rather than January of 2008. Given more time to build a rapport with the team, Fletcher is better able to convince players like Mats Sundin and Tomas Kaberle that their departure will eventually be better for the club in the long-term. The Kaberle trade, indeed, turns out to be the gift that keeps on giving; from dealing Tomas Kaberle, the Maple Leafs now have Jakub Voracek, John Carlson, Sean Couturier, Brendan Warren, and a 5th-Round Pick in 2018. Sundin spent far too long in Toronto for his legacy to be affected by one simple trade, and he is just as loved by Leafies in this timeline as he is in the OTL. Fans also have an appreciation for Kaberle, if not for his solid play on the ice, then for the assets his trade has given the club today.

From Pittsburgh’s Perspective: The day after the draft, Pittsburgh’s hockey media is left in a collective state of shock. Sebastien Caron was by no means good. His time to shine had come and gone, and with Marc-Andre Fleury on the rise, it wouldn’t be long before Caron was surplus to requirements, even as a backup. But Rask? Tuukka Rask?!? Writers and broadcasters across the hockey world were struggling to find an answer as to why Toronto would pay the price of a fantastic goaltending prospect – one with the potential to be an elite starter in the NHL – for a goalie that had been one of the worst in the league that year. In any case, Caron was no longer the Penguins’ problem. They now had to focus on finding a new deputy for Fleury, who was still having a few struggles as a starter. But their future was now a little bit more secure with Tuukka Rask. If Fleury, for whatever reason, didn’t work out, they now had themselves a great replacement ready to go in a few years’ time.

2006-07 comes along, with Jocelyn Thibault (formerly of Colorado, Montreal, and Chicago) brought in to be Fleury’s backup when needed. But the real big addition is in the centre spot. Yes, they already have Sidney Crosby, but now, they need a replacement for the now-retired (again) Mario Lemieux. They have a pretty damn good one: Evgeni Malkin. Drafted 2nd Overall in 2004, Malkin has already been the subject of a few controversies in his attempts to move to North America to play for the Pens. Pittsburgh wanted this guy, BAD. Malkin’s rookie year was ridiculous, as he put up 85 points in 78 games, winning the Calder Trophy as the rookie of the year. Sidney Crosby, meanwhile, led the league in points, and won the Hart Trophy as league MVP; the man once christened as “The Next One” was now simply “The One”. Despite the improvement of their young talent, Pittsburgh struggles in their first playoff appearance since 2000-01, being eliminated by the Sens in 5 games.

Now, at this point, I’m going to skip the next couple of seasons. You may have noticed that the above paragraph is just a re-telling of what happened in real life. The reason for this is because despite the shock trade for Rask, nothing really changes with the NHL roster. They still continue to make progress up the standings, and they still become a Cup contender. They still face Detroit in the Cup Final two years in a row, losing in 08 and winning in 09. The main focus at this point is in the AHL, as Wilkes-Barre/Scranton is home to a rapidly improving goaltending prospect. For the first two years of his career in North America, Tuukka Rask plays the bulk of the games for the WBS Penguins. His first year in the league, he leads the team all the way to the Calder Cup Final, only to lose to the Chicago Wolves. His play is by no means amazing, but the team in front of him is just so good that a Cup Final appearance is a given. In 08-09, however, things turn around entirely; the Penguins are eliminated in the second round by the Hershey Bears, but not due to Rask, who is absolutely spectacular in the 10 games that he plays (6-4-0 record, .930 SV%).

As 2009-10 comes along, the Penguins now have choices to make. Dan Bylsma, who led Pittsburgh to the Stanley Cup after replacing Michel Therrien mid-season, is adamant that Tuukka Rask is ready for NHL playing time. As a result, the Pens forego signing Brent Johnson, instead electing to give Rask an NHL roster spot going into the season. Fleury is still the goalie of choice, having just won the Cup for Pittsburgh, but when he is called upon, Rask is excellent. He plays 23 games, managing a .931 SV%; of course, a few of those games were in relief of Fleury, who had begun to regress a bit as the starter. Fleury is still the goalie of choice in the playoffs, however, and starts every game as the Pens go two rounds deep, losing to the Montreal Canadiens in seven games. The first whispers of a goalie controversy are beginning to be heard, but Ray Shero and Dan Bylsma insist that Fleury and Rask will get along fine.

At the beginning of the 2010-11 season, it is once again Fleury who starts. With Rask backing up. The Finnish netminder isn’t quite as amazing as he was the previous year, but he is still a top-tier backup, registering a .919 save percentage in 23 games. Rask’s biggest contribution to the Pens, however, comes in a late-season game against the New York Islanders. In a game that had both sides trading hostilities, the anger culminated in a rare goalie fight between Rask and Islanders’ netminder Rick DiPietro. Rask needed only one punch to win the bout, leaving the former New York #1 Pick concussed. The following week, Tuukka was nearly involved in another fight, this time with Islanders agitator Micheal Haley. Rask may well have won that fight, too, had teammate Eric Godard not bolted off the bench to take the fight in his place.

The playoffs came about, with Pittsburgh matched up against the Tampa Bay Lightning. Fleury is once again the designated starter for the Penguins, but he is unable to replicate the form of a couple years prior; his .899 SV% has fans starting to call for Rask to get more playing time in the future. In the end, the Lightning end up with a seven-game victory, but fall to the Bruins in the Conference Final. The Pens, finishing with the 23rd Pick, select defenseman Joe Morrow.

2011-12 comes about, and nothing has changed from the previous year in goal. Despite this, fans are becoming more and more frustrated with the play of Fleury, especially in the playoffs. Rask, now somewhat of a cult favourite within the Pittsburgh fan base thanks to his apparent knockout power, still continues to serve well as the second-stringer. The team in front of them is just too much for anyone else to contend with, and the Pens finish at the top of the East, drawn against Washington. The two sides had clashed before to much fanfare, thanks to the hyped rivalry between Sidney Crosby and Alexander Ovechkin. This iteration of the series proved to be incredibly entertaining, with goals, hits and fights galore (including the now-notorious 10-3 Caps win in Game 4). In the end, however, it is Pittsburgh that prevails in seven games. They are drawn against New Jersey in the next round, and despite home-ice advantage, the Penguins are eliminated in five. At this point, fans have begun to boo Fleury following poor performances at home, with Game 5 of the Pens-Devils series giving birth to the “We Want Rask” chant, one that would only get louder and louder as time went on.

Despite fears that the season would be nixed entirely, a late agreement between the NHL and NHLPA means that the 2012-13 NHL season will be played after all, starting in late January. As per usual, Fleury is the man that Pittsburgh’s management is firmly behind, with Rask once again seeing the bench most of the time. Across the league, hockey writers are wondering why Rask hasn’t been traded to somebody that needs a starting goalie, an echo to Vancouver’s situation with Roberto Luongo and Cory Schneider. Boston, in particular, is thrown around as a destination, as they have just suspended Tim Thomas for failing to show up to training camp, and will likely cut ties with him for good. Rask, to his credit, does nothing to ignite the flames of controversy off the ice, but does add to the chatter thanks to his brilliant on-ice work. The Penguins take advantage of the shortened season to dominate the East, clinching 1st in the East with a 36-12 record. Given the New York Islanders in the first round, the Pens make short work of their rivals from a couple years ago, winning in six. They end up staying in New York, forced to deal with the Rangers in the second round. It actually ends up easier for the Pens, who dispatch the Rangers in five games.

Next up is the Montreal Canadiens, who were coming off of an intense seven-game series with their long-time rivals Toronto, and a spectacular late-game comeback against the Boston Bruins in Game 7 of the first round. Pundits predicted that they were too emotionally spent to last against such a strong Penguins team. Instead, the Habs run on pure emotion, claiming the first three games of the series. Faced with almost certain elimination, Dan Bylsma finally decided to give the Pens fans what they had been waiting for all this time: Tuukka Rask. Game 4 comes along, and Rask vindicates all those fans who were calling for him to start with a shutout victory. He is once again in net for Game 5, and delivers another win, this time in front of an adoring crowd at the Consol Energy Center. Game 6 and Game 7 are both in Rask’s favour; not only did Rask step in to win the series, he did it from a 3-0 deficit, the first time since Philadelphia defeated Boston that way in 2010, and the 4th such occurrence in NHL history. He continued to be effective against the Blackhawks in the Stanley Cup Final, but Chicago is just too strong to be stopped. Thanks to a pair of goals in 17 seconds in Game 6, the Hawks win the Stanley Cup for the second time in four years.

The Pens now have questions to ask of their goaltending in the off-season. Marc-Andre Fleury would be going into his free-agent year in 2014, but Rask had to be re-signed NOW. Fleury was slowly slipping behind, and had relinquished the starting role in the playoffs to Rask, who looked ready to take the starting job that fans had been demanding he be given for so long. After deliberation over the next few days following the Stanley Cup Final, a decision likely has to be made by the Pens’ brass at Draft Day. Teams are clamoring for one of Pittsburgh’s two starters. Rumours fly across the floor of the Prudential Center in Newark, New Jersey, and all over social media; reporters are constantly checking in with sources who are busy hypothesizing about deals with teams such as New Jersey, San Jose, or Toronto. Eight picks in, the Commissioner is informed of a deal, and takes a trip back to the podium to deliver the news.

Gary Bettman: (fans booing) We have a trade to announce… (boos continue) You’re gonna want to hear this… (boos subside) The New Jersey Devils trade their natural 1st-Round Pick in this Draft, which is the 9th Overall Pick, to the Pittsburgh Penguins, for goaltender Marc-Andre Fleury.

The New Jersey fans in the audience burst into cheers, having seen their team secure their future in goal. Marc-Andre Fleury was now a Devil, the man hand-picked by the front office staff to be the replacement for Martin Brodeur, arguably one of the best to ever play between the pipes. Pittsburgh, too, have made their choice. After so many years of waiting, Tuukka Rask will finally get his chance to be a starting goalie with the Penguins. After all, when he has been given the chance, he has shone. And never was this more apparent than in the last playoff run, where he was key in helping the Pens overturn a 3-0 series deficit to win over the Canadiens. It’s about time that they gave him a chance to prove himself as a full-time starter, and Ray Shero makes no mistake of it by signing Rask to an eight-year extension, the max allowable. (As for the pick that Pittsburgh acquired, they use it on centreman Bo Horvat. They had traded their natural selection in that round to Calgary, who used it on Jason Dickinson.)

After so long being the backup, Tuukka Rask was now the man in goal for Pittsburgh going into the 13-14 season. Behind him in the depth chart is Jeff Zatkoff, a former Los Angeles draft pick and 2007 World Junior selection for U.S.A., who was no threat to his job. Rask excelled in his first full campaign, playing 64 games, and registering a save percentage of .930, best among all starters. He is named an All-Star for his efforts, as well as winning the Vezina Trophy. Thanks to his amazing play in goal, the Pens finish on top of the Metropolitan Division with 111 points, matched up against Montreal once more. This time, no dramatic comeback is necessary, as the Pens win the series 4-2. This pits them against the New York Rangers in the next round, and despite Rask continuing to play well, it’s the Rangers that prevail in seven games. The Pens end up with the 22nd Overall Pick in the 2014 Draft, taking Finnish winger Kasperi Kapanen.

The Pens know now that they have likely made the right decision. Sure, Marc-Andre was pretty good, but Tuukka was Vezina good. Fleury had done okay with the Devils, but they weren’t really close to the playoffs, while Rask had been a big part of the Penguins being on top of the Metro Division. But while Rask stays, the coach and GM that put so much faith in him don’t. Feeling that the team needs a change of ideas in order to continue to be competitive, the Penguins sack both Ray Shero and Dan Bylsma in favour of Jim Rutherford and Mike Johnston, respectively. Rutherford was the man who managed the Carolina Hurricanes to their 2006 Stanley Cup, while Johnston came to the NHL following eight years with the WHL’s Portland Winter Hawks. In an interview early on in the pre-season, Johnston informs a reporter that he has no intention of changing the starting netminder, giving Rask a chance to concentrate on the season ahead.

2014-15 is a step back for a Penguins team that had once been the team to beat in the Metro Division, as they barely hold on to a playoff spot with 99 points. Rask plays 64 games, managing a record of 34-19-10, and a save percentage of .922, slightly off from his total the previous year. Faced with the New York Rangers in the first round, the Penguins try their best to make a series of it, but are eliminated in six games – not the kind of start that the ownership group wanted from Rutherford and Johnston. Feeling some pressure on him, Rutherford decides to make a big splash in the off-season, signing off on a blockbuster trade with the Toronto Maple Leafs. The key piece of the deal going to the Pens is scoring winger Phil Kessel, a player who goes on cold streaks sometimes, but when he’s hot, he’s aflame. Included in the trade the other way are Pittsburgh’s 1st-Rounder in 2016, as well as prospect Kasperi Kapanen, among other assets.

Now, the pressure is on, not just for the management group, but for Rask. Big things are expected with a player like Kessel added to a line-up that boasts the likes of Sidney Crosby, Evgeni Malkin, Kris Letang, and Patric Hornqvist, among others. The Pens start off poorly (by Penguin standards), and after a 15-10-3 opening to the season, Mike Johnston is fired, replaced by Wilkes-Barre/Scranton head coach Mike Sullivan. Sullivan takes some time to get the line-up in shape for the playoffs, but eventually, he figures out the tactics he feels he needs for a long Cup run. The playoffs start with Pittsburgh up against the Rangers again. Early on in the series, Tuukka Rask is injured, knocked out for the rest of the playoffs. With their starting goalie now out of the picture, the Pens turn to Matt Murray, who had spent some time with the NHL Pens that year, to take them through. To the surprise of almost the entire hockey world, Murray shines in the spotlight. First, it’s the New York Rangers in five games, then, it’s the Capitals in six. Third up were the Tampa Bay Lightning, but they, too, were unable to solve this unknown goalie, losing in seven games.

The stage was now set for the Stanley Cup Final, with Pittsburgh facing the San Jose Sharks. The Sharks had a hot goalie of their own, in former Toronto starter James Reimer, who, like Phil Kessel, was traded by the Maple Leafs the previous off-season. Mike Sullivan now had Rask available once again, but elected to ride the hot hand, giving Murray the nod for Game 1. Murray had hiccups, but proved that the first three rounds were no fluke. He would prove to be solid all the way through as the Penguins claimed their 4th Stanley Cup, a six-game win over the Sharks. Phil Kessel, cast off by the Leafs, was a big part of the playoff stretch, leading the league with 22 points in the post-season – on the third line, no less. For Jim Rutherford, it was the fruition of the plans he had made in the off-season, but for Rask, it was somewhat bittersweet. Yes, he had a Stanley Cup ring, but he was the backup, relegated to the bench in favour of the younger netminder. To Pens fans, and the hockey world, it sounded rather familiar.

As the 2016-17 season came closer, there was once again a goalie controversy in Pittsburgh. Matt Murray seemed ready to assume the starting job from Tuukka Rask, who was now in the same position as Marc-Andre Fleury was just a few years ago. Publically, Rask was quiet about the whole thing, and there seemed to be little chatter behind the scenes about any disgruntlement from the Finnish keeper. He was a Penguin first, and a goalie second, and would not try and throw Matt Murray under the bus for the sake of his own career. For the most part, it was Murray who started that year, playing 49 games as compared to 38 for Rask. Murray was still impressive, recording a .923 save percentage, but Rask’s .915 was nothing to sneer at, either.

At the beginning of the playoffs, it was Rask whom Mike Sullivan named as the starter of choice for the team’s series against Columbus. He would play all five games against the Blue Jackets, winning four. He would have a few wobbles against the Capitals, including a tough 5-2 loss in Game 6, but the coach stuck to his guns, keeping Rask in for the decider. Rask repaid his coach’s faith with a shutout win, sending the Pens on to the Conference Final against the surprising Ottawa Senators. The first two games were split 1-1, both low-scoring, but Game 3 saw Rask shelled for 4 goals on 9 shots in a 5-1 loss. Matt Murray was in, and had the task of keeping the Pens in it as long as he could. His goaltending proved to be decisive, as the Penguins won Game 7 in a double-overtime victory. Murray would be in goal for all six games against the Nashville Predators, and came up big again; his last two games were both shutouts, as Pittsburgh won Game 5 and 6 to claim a second-straight Stanley Cup.

Amidst the celebration, there was now serious concern for Tuukka Rask’s spot. Much in the same way he had taken over for Marc-Andre Fleury, he was now being usurped by a younger, cheaper goalie. It was even more of a concern considering the upcoming expansion draft, in which teams were allowed to protect only one goaltender. With Murray being so effective in clutch situations, it seemed like Tuukka Rask was now expendable. Indeed, it was his name left on the unprotected list; given the chance to claim a former Vezina-winning netminder, the Vegas Golden Knights jumped at the opportunity, naming him as their very-first selection during the NHL Awards Show. Rask endeared himself very quickly to Knights fans, appearing on stage in a VGK jersey to the elation of the Vegas crowd.

The Penguins Today: When you look at the Penguins in the OTL, and the Penguins in this timeline, there are almost no differences. They are still two-time Stanley Cup Champions, and still have a formidable troika of forwards in Sidney Crosby, Evgeni Malkin, and Phil Kessel, ready to strike at any moment, or be unleashed together in important situations. But what becomes more of a factor in this timeline is their goalie development. Ever since the 2005-06 season, it seems like the Pens have had somebody who was on the roster, and ready to be a #1 goalie. At the start, it was Marc-Andre Fleury, who managed a few great years with Pittsburgh, including a Stanley Cup. And when he began to falter, they had Tuukka Rask to replace him; Rask never directly won a Cup for the Penguins, but he did manage a Vezina Trophy in 2014, and was still a consistent starter for the Pens for a couple of years more. And when Rask was out of the picture, it was Matt Murray who stood in for him, quite admirably. Murray came in on an emergency basis in both 2016 and 2017, winning the Stanley Cup both times.

The infamous trade of 2006 now looks, from Pittsburgh’s perspective, like an absolute heist.  Sebastien Caron tried hard, but in the end, was nowhere near good enough for the Penguins going forward. For all intents and purposes, the trade with Toronto was like having a goalie prospect fall right into their lap. It proved, arguably, to be Ray Shero’s masterstroke, a deal made almost out of thin air. It gave the Penguins an elite NHL goalie, and left the Maple Leafs holding, essentially, an empty sack. Among Pittsburgh faithful, the name “Tuukka Rask” will not be forgotten any time soon. Whether it was for his patience as a back-up, his brilliance as a starter, or his one-punch knockout of Rick DiPietro, Pens fans will always have something to remember about #40 in black and gold.

From Boston’s Perspective: At this point, we should take a moment to examine how this new reality affects Boston, both immediately, and in the near future. In this timeline, Peter Chiarelli is unable to make the deal to get Tuukka Rask, and now has to find his team a goaltending prospect for the distant future (which, in the scope of hockey, means 3-5 seasons from now). Hannu Toivonen has graduated to the NHL roster, and will likely suit up in a 1A-1B situation with Tim Thomas. Their immediate future is set. At the AHL level, they now have to find somebody to provide backup to Jordan Sigalet. (They rectify this, both in the OTL and this reality, by picking up Phillippe Sauve and Brian Finley during the off-season.) But now, without the Rask deal, they have to find a younger prospect. What better time than at the NHL Draft that they were in the middle of conducting?

Boston has the 37th and 50th picks in the 2nd Round, and will likely use one of them on a goalie. The most appealing choice at this point, Czech youngster Michal Neuvirth, goes off the board at #34 to Washington. Chiarelli knows he has to act quickly, and when he gets to pick #37, he selects Jhonas Enroth from Sodertalje in the Swedish Elitserien. Enroth comes into this timeline replacing blue-liner Yuri Alexandrov, who never makes it to the NHL, and only spends one season with the Providence Bruins in the OTL. Their 50th pick doesn’t change, as they still use it on forward Milan Lucic. Enroth doesn’t end up in North America until the 2008-09 season, but it’s not really of any concern for the Bruins, who won’t use him for a couple of years.

Come the 2010-11 season, Enroth is slotted in as the backup to Tim Thomas. He only plays a handful of games, but does well whenever he is given a chance. As with the OTL and Scenario A, the Bruins are still winning the Stanley Cup this year. The only thing that changes is the fact that they now face Toronto in the first round, winning the series in five games. 2011-12 sees a slight change, as the Bruins don’t face the Capitals in the new timeline, instead matched up once again with the Maple Leafs. Like in 10-11, Boston prevails, but they are knocked out in Round 2. With Tim Thomas getting suspended from the team in the lockout-shortened 2013 season, the starting job is Enroth’s to lose. He plays pretty well, managing a .909 SV% in 32 games, but he just can’t hack it in the playoffs, as the B’s lose in the first round to the Montreal Canadiens.

The following year sees Boston once again running Enroth as their starter, but he regresses; given 48 games, he manages a .906 SV%, and the Bruins are swept in the first round by the Columbus Blue Jackets. Now, the pressure is on. He starts off 2014-15 as the starter, and it becomes clear that he can’t keep up in a long stretch of games. He is outplayed by backup Niklas Svedberg, and the Bruins, fading from the playoff race, trade their former 2006 2nd-Round Pick to Dallas. At the 2015 Entry Draft, much like the OTL, they make the trade with L.A. that sees Martin Jones join the Bruins, but they hold on to him, rather than ship him to San Jose; this is, of course, the same thing that happens in Scenario A.


March 10th, 2018


“You fuckin’ idiot! Rask for Caron! RASK FOR FUCKING CARON!”

John Ferguson Jr. looks up from his seat, over to his right at the fan that is clad head-to-waist in Toronto Maple Leafs gear. (He couldn’t find a pair of Leaf pants that would fit him.) He gives a sarcastic half-smile, shakes his head, and turns his attention back to the game, away from the inebriated heckler. He doesn’t need to give the guy any more acknowledgement, as he knows that arena security will deal with him. They always do.

John has heard it all before: the anger from fans, the familiar refrains involving the words “Rask”, “Caron”, or, more likely, both. Of course, like with this fan, there’s always a few curse words thrown in for good measure. Even almost twelve years on from the day it happened, it seems to be a trade that he would never get away from. He’s never tried to offer any kind of rebuttal, or engage in a debate with the fans, many of whom are simply using him for venting out their alcohol-fueled frustrations. The trade has reached a state of infamy that very few deals get to; the way that Oilers fans talk about the Gretzky trade, or the way that Capitals fans talk about the Forsberg-Erat deal, Leafs fans talk about the deal that sent Tuukka Rask to Pittsburgh for Sebastien Caron. Today, the deal is viewed as the very worst in Leaf history, with other deals of the past (e.g. Courtnall-for-Kordic, or Kurvers-for-Niedermayer) now taking a back seat to that one Draft Day trade. It not only cost Ferguson his job, but after an interview that happened a few years later, it cost him any sort of career working in an NHL front office.

The trade was bad enough. But it was when the trade was made that truly proved the nail in the coffin for his reputation. In an interview with the Toronto Sun’s Steve Simmons in June 2013, Caron – then playing with Iserlohn in the DEL – talked about what he was doing on the day he was traded. “I was talking with my agent, who was in a phone conversation with Ray (Shero),” Caron said. “We were in the process of discussing my buyout, and making me a free agent. Suddenly, Ray says that he has to call us back, because he’s got a deal to make. I get it, it’s Draft Day, and these things are going to happen. But when he gets back on the phone to talk to us, we get told that he just traded me to the Maple Leafs.” If the Leafs were so desperate to get Caron at the time, they literally could have waited minutes to sign him as a free agent. Instead, they gave up an elite NHL netminder for the man now viewed as the worst goalie in Leaf history. (Even Vesa Toskala, to this day, has his defenders, but nobody will ever go to bat for Caron.)

Ferguson, at the time of the interview, was a scout for the San Jose Sharks, but he was cut loose after the 2013-14 season, when his contract expired. Ever since then, he has been an on-camera personality for the NHL Network, in charge of doing their Draft Rankings. For the past couple of years, his rankings have been some of the most accurate, and he seems to have a knack for identifying players who end up being late-round sleepers. Today, he is scouting Andrei Svechnikov, believed to be the top prospect based in North America. Svechnikov already has an assist, and with the Barrie Colts on the power play, he is on the ice looking for another point. Ferguson watches intently as the Russian prospect looks to make a play to put his team ahead 5-2. The fan from earlier tries to break his concentration with another shout of “RASK FOR FUCKIN’ CARON!”, but Ferguson gives him no heed, keeping his focus on the ice. Just then, Svechnikov feeds a pass to his countryman, Dmitri Sokolov. Sokolov finishes, and the Colts are up by three goals against the Peterborough Petes.

Maybe one day, John Ferguson Jr. can truly acknowledge the taunts and heckles. Maybe one day, he can laugh at all of it, and joke over a few drinks about the boneheaded trade he made. And maybe one day, he can look at the bright side of that trade, and embrace the indirect role he had in the Leafs’ rebuild in the late part of the decade; after all, it allowed the Leafs to bring back Cliff Fletcher, who was able to bring in the pieces that made Toronto a playoff team again. For now, though, it will have to wait. Andrei’s a bit more important.


Coming up next month: A cautionary tale of restricted free agency – What if the Buffalo Sabres never matched Thomas Vanek’s offer sheet?

Also, if any of you have an idea that you’d like me to explore for The Big “What If”, please let me know in the comments. The more ideas, the better!


  1. Like I already said, great read.

    I’d love to see a post about the Avs never matching the Rangers’ offer sheet for Sakic in 1997.

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