5. Matt Duchesne vs Colorado
The Colorado Avalanche, his favorite team as a child, drafted him third overall in 2009. Duchene spent the next nine seasons as one of the franchise’s greatest players, scoring the fourth-most goals (178) since they moved from Quebec in 1995. But Duchene felt it was time to leave the team, before his contract was up in summer 2019 and before it entered yet another rebuilding phase — so he had to ask the team’s general manager Joe Sakic, his favorite player growing up, to move him.
“Asking for a trade out of Colorado, from Joe Sakic, who was my idol, was the hardest thing I’ve ever had to do,” Duchene said the Senators acquired him in a three-way blockbuster trade that sent center Kyle Turris to the Nashville Predators and seven assets — players and picks — to the Avalanche.