I think the alternate history is him being on a team that actually makes the playoffs. Of course, one could argue that the teams he was on didn't make the playoffs because he was getting minutes.
16 year career but let's turf his "rookie" five game season in LA and his 2021 season of 13 games with the Rangers. So a 14 year career and he's only played in 33 total playoff games. He's only been in the playoffs seven times so do the math on how often he has gotten out of the first round. This might be the first time he has and he's only playing due to injury...don't even think he played in Round 1.
Anyways, the point is that he finally made the playoffs in LA and then got moved for the final piece of the Kings puzzle, going to a team that would then miss the playoffs for the next two seasons, make it once and then not make them again for another three seasons. In LA, he was a PPG over 12 games in the playoffs while playing 23 minutes a night. In Columbus, he's 9 points in 11 games while playing 28 (!) minutes a night.
Those numbers pretty much demolish his regular season totals and support the eye test that told you "Jack Johnson plays differently in big games". By the time he got to Pittsburgh though, he was pretty much done. Would have been nice to see him get more cracks at playoff games during his 20s.
I'm not a fan of any of the remaining teams. Both ECF teams are a huge pass and Edmonton goes without saying. The born on 3rd, think they hit a triple Avs fans have suffered a lot since dominating right out of the gate so they are the choice to stomach at this point: it would be cool for Johnson to get a Cup after all that he's been through.
Would personally be hilarious for me as well if MacDermid could get his name on the Cup after all the shit he has been given on this Board.