The 2008-2009 season was nearly a lost one. By the trade deadline, they’d clawed their way up to 12th in the Western Conference, Manny Legacy was broken by Sarah Palin, and despite weeks of strong play it didn’t look like the Blues were going to make the playoffs. You could forgive then-GM Larry Pleau for being a seller at the deadline, especially when one of the players he was going to sell was 36 year old Keith Tkachuk. Big Walt had already been a rental a couple of years prior to the Atlanta Thrashers.
According to Jeremy Rutherford of The Athletic (subscription required, but it’s worth it just for JR and for this article - he’s got some great stuff from Walt and Pleau in there), Tkachuk was almost a rental for the Boston Bruins. Pleau asked him to sign his NTC and pack his bags to head to Boston with a 20 year old David Perron in exchange for...
... pending RFA Phil Kessel.
The Blues could’ve had Phil “The Thrill” Kessel: American Hero, had the Bruins not scuttled the deal. Walt and Perron stayed, the Blues made the playoffs, and then got swept by the Canucks.
There was a part of me that went “God dang it” as I was reading this. Phil finished the 2008-2009 season with 34 goals and 26 assists. That would’ve been nice to have on the Blues. But at the same time, the Blues wound up with a similar result that they probably would’ve had if the trade had gone through. Who’s to say that the loss of a locker room stalwart like Tkachuk wouldn’t’ve killed the team morale that they obviously had going through the incredible post-deadline run to the playoffs?
As I mentioned before, Kessel was a pending RFA who turned down a four-year, $16 million contract offer from the Bruins to head to Toronto in exchange for two first round picks and a second rounder. The two first round picks - center Tyler Seguin and defenseman Dougie Hamilton - are tearing it up with the Stars and Hurricanes, respectively. That goes into a further level of what if. What if Kessel had walked from the Blues to the Leafs, and the Blues wound up with Seguin and Hamilton - and managed to retain both of them?
Tkachuk retired in 2010 as a Blue and has stayed put in St. Louis. David Perron would’ve probably come back ten times anyway, as it’s become evident that this team can’t quit him and vice versa.
What would’ve happened had the trade gone through? Who knows. Speculative revisionist history is a favorite past-time of the Blues, like “what if Wayne Gretzky tried to play defense” and “why didn’t the team draft Toews first overall instead of Erik Johnson?” Odds are good that things would be just as they are now. But hindsight is 20/20, close only counts in horseshoes and hand grenades, and so on and so forth.