Detroit Red Wings
Detroit Red Wings GM Steve Yzerman has an Yzer-plan to get the Wings back into contention much like how he helped transform the Tampa Bay Lightning into the juggernaut they are today. According to DetroitHockeyNow, Yzerman was not very pleased with the "level of competitiveness" of his team down the stretch, especially given they lingered in the playoff picture for a little while during the 2021-22 season.
Couple Yzerman's displeasure with the fact that the Boston Bruins have taken a few massive hits this offseason already with a plethora of injuries such as Charlie McAvoy, Brad Marchand, and Matt Grzlyck that could hold them all out for significant time, and the idea that its possible captain Patrice Bergeron might not return, the 2022-23 season could be the first time in a long time the Bruins don't make the postseason. That leaves the door wide open for one of the outside teams looking in, like Detroit, to step up and put themselves in the playoff picture.
The Red Wings will need to add a few pieces to their roster this summer in order to improve their chances, but with $35,771,111 in projected cap space this summer, they have plenty of money to do so. Bailey could certainly be an option for Yzerman as a solid middle-six option, and although Barry Trotz's future is still undecided, there's an outside possibility he could buy into Yzerman's plan if he decides he wants to be behind the bench in the 2022-23 season. A familiar face in Bailey could help sway him there, too.