The Toronto Maple Leaf fan base no longer has the market cornered on Tuukka Rask regret.

After drafting Tuukka Rask 21st overall at the 2005 NHL Draft, the Toronto Maple Leafs famously pulled off one of the worst trades in franchise history, dealing Rask to the Boston Bruins for goalie Andrew Raycroft. Rask became a star goalie in Boston for the better part of 16 years, while Raycroft lasted two years in Toronto, putting up below-average numbers.

To make matters worse (or better, depending on your allegiances) Boston apparently would have accepted Toronto goalie Justin Pogge as compensation in the trade. In fact, Postmedia later reported the Bruins had actually been thinking of releasing Raycroft.

Now Ottawa Senator fans can join their Leaf counterparts in bemoaning the one that got away.

First, let's be clear. Second guessing draft decisions, years after the fact, is a unfair game you can play all day with even the best NHL amateur scouting staffs. It's not far removed from asking someone, the day after the draw, why they didn't choose the winning lottery numbers. 

But here's something that adds another layer to one of these draft day tales of what might have been. 

Fans usually never find out the juicy details about just how close their team was to drafting certain star players. But Rask took care of that this week on the Spittin' Chiclets Podcast. 

[embed]https://www.youtube.com/watch?v=tPX7N-8jlKY[/embed]

Rask revealed that leading up to the 2005 NHL Draft, the Senators were talking to him more than any other team in the NHL. Ottawa had the ninth overall selection that season.

"There were some rumours that Ottawa would pick me," Rask said. "(The Senators represented) the most interaction I had from all the teams.

"And then after that, I had no idea. Because I think (the Senators) were number nine or something. They didn't pick me and then (the draft) just kept going and going. I had no idea who might pick me. I was just hoping that first-round choice would come and then Toronto picked me (at 21)."

In fairness, NHL teams are historically skittish about using a top ten overall pick on a goalie. As most fans know, goalies are notoriously hard to evaluate and take longer to develop. So the Senators, who didn't have a second round pick that year, deserve some credit for seeing enough excellence in Rask to even consider drafting him that early. But ultimately, they made the decision to go with someone else they liked even better. 

So which skater did former Senators GM John Muckler and his staff believe represented a clear upgrade at ninth overall? Who did they see as the much better bet to be an impact player in the league than this young Finnish goalie they really liked?

That would be defenceman Brian Lee. 

Just like Tyler Boucher 16 years later, Lee was thought of as a good American prospect, but almost no one had him ranked inside the top 10.

With the Sens in the midst of their glory years, Lee then started down an amateur path that's highly familiar to Sens prospects – playing at North Dakota and for Team USA at the World Junior Hockey Championships. But things never quite panned out in Ottawa, not the way you'd expect for a top ten pick. 

Over parts of five seasons, Lee played 167 games, scoring 28 points. He was eventually traded to Tampa for Matt Gilroy, who played only 14 games for the club. And so the Brian Lee trade tree died right there. 

After a couple of years with the Lightning, Lee retired from the game at 26 due to a lingering knee injury. Rask, on the other hand, went on to a career in Boston that might soon take him to the Hall of Fame.

As with all draft day regrets – and with a nod to Rod Stewart – the Senators wish they knew then what they know now. It's finally something Sens and Leafs fans can agree on.

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