2. Detroit Red Wings
This one is slightly out of left-field but it actually makes a lot of sense the more you think about it for a whole bevy of reasons. For starters, one of Sam Bennett’s reported reasons behind wanting out of Calgary is that he wants a bigger role. Well, he would almost certainly get that with the Detroit Red Wings given that they are pretty much devoid of any talent outside a handful of players.
It worked for Robby Fabbri who was traded by the St. Louis Blues to Detroit and, in need of resurrecting his career, the forward went on an absolute tear with the Red Wings in 2019-20 with 31 points (14 G, 17 A) in 52 games, and Bennet could do similar given that he will almost certainly be given the opportunity to establish himself as a top-six forward for Detroit.
Detroit have the cap space to make it work – just under $7 million according to CapFriendly – and they also have a bounty of picks that they could send to Calgary, in addition to an established forward in either Bobby Ryan or Vladislav Namestnikov if the Flames want a player back who can slot straight in and contribute.
Plus, for Sam Bennett, he is a RFA after this season so he will have an opportunity to either boost his stock and market value in order to attract the attention of more teams, or he could decide that the Detroit Red Wings are the team to give him the bigger role he craves and opts to sign a bridge deal that would work for both franchise and player.