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Remember back in 2006? Mike O'Connell had just been fired back in March and the Boston Bruins had a massive hole in the front office at the position of General Manager.

Enter Jeff Gorton, and one of my all-time favorite trades in hockey history.

For the Bruins, Andrew Raycroft had seemed to be a real potential star. He won the Calder in 04, just before the lockout, and got Vezina votes the same year. But after the lockout and the shock trade of Thornton to San Jose, the 05-06 Bruins fell apart completely, posting absolutely terrible numbers and finishing bottom five in the league. Raycroft had completely flipped and started playing poorly (and through injuries), posting a sub-.900 SV%. Tim Thomas, in the meantime, had shown up completely out of nowhere at like, age 30, and so Raycroft became expendable.

Meanwhile, in Toronto, the goaltending situation couldn't have been the opposite. Belfour had gotten old, Tellqvist wasn't doing hot, and Aubin was a career backup. In the system, they had Justin Pogge, who had posted really solid stats while playing with the Hitmen, and a young Finnish goaltender that they'd drafted in the first round in 2005, who'd posted great numbers in Finland and at the World Juniors. Neither of those guys would be the immediate fix though, so Toronto sought experience that might bolster their goaltending now.

The trade?

Toronto receives Andrew Raycroft from Boston in exchange for the rights to that young Finnish goaltender.

Tuukka Rask.

Raycroft would go on to be an absolute disaster for the Leafs, posting a sub-.900 SV% in 72 starts in his first year with them and would eventually be bought out of his contract in his third year with the team. They would go on to have a ridiculous carousel of goaltenders that only continues to date.

Meanwhile? Boston bolstered their team with Thomas while Rask developed and eventually became a Hall of Fame netminder that would, on multiple occasions, literally come back to haunt the Leafs in the playoffs. Rask became exactly the goaltender that Boston wanted him to be and Toronto wrote their own death warrants by handing him to a division rival. Even today, Rask still stands as the winningest goaltender that Toronto has ever drafted.

And every single win was with the Bruins.