Crosby2010
Registered User
- Mar 4, 2023
- 1,274
- 1,113
See my issue with the idea of the Oilers contending for more than 1 cup is this:
Even if we pretend the laws of financial gravity no longer apply and all of the oilers core players stay, are happy and motivated to keep winning, and money is no object, pittsburgh, calgary, and later detroit/chicago/vancouver still exist and are coming hard for future seasons
If Gretzky stays, they beat Calgary in a 7 game war in 1989 similar to what happened in 1991 in our timeline, there is no way the Flames just fade away for 1990. The flames organization will correctly recognize that winning a cup is vital for the clubs long term survival and reload with as many upgrades as possible. As it is Im not sure a complete 1988 Oilers roster could have survived the 1989 Flames.
And that cycle will repeat with the Penguins, the Blackhawks peaking for 1991/92, eventually the Red Wings. Where exactly can you see more than 2 winnable cups in the 1989-1997 window for the 80s Oilers? If they win in 1989, theyll be relatively gassed after 3 straight cups to deal with Calgary the next year, and if they say win a 1991 final against the penguins, I think its pretty likely the Pens use that experience to win the next one.
I think they win again in 1989, and I do realize the Flames would not be an easy out, but this is still a Gretzky-Oilers team. They had just thrashed the Flames in a sweep in 1988. The Flames would be even hungrier in 1990, and again this wouldn't be easy, but let's keep in mind that Gretzky and the Kings beat the Flames in 1990. I don't know what else they do to be honest. No one knows for sure, but they would be perennial contenders well into the mid 1990s at least. If that is the case I don't know how they can't squeeze more than just the 1989 and 1990 Cups out. Mario and the Pens eventually figure it out, Roy never wins in 1993 and the Rangers never win in 1994 because there is no Messier/Oilers core there. The game doesn't tighten up and the Devils never win in 1995 either. Basically you can argue the dead puck era is either delayed or never happens, and this only benefits the Oilers. I am not saying they go 8 in a row like the 1960s Celtics, but could they win 5 in a row up until 1991? Yeah sure. And like the Golden State Warriors who won in 2022 I think there would be that extra Cup they win that isn't a shock but is one of those "They still got another one in them" type of championship that surprises no one. If I had to guess, 4 more Cups for Gretzky (1989, 1990, 1991 and maybe 1994?) Messier wins 8 overall too. They are still decent post 1994 but this is when it starts to fade a little, at least for their standards. And another thing we have to ask, does Gretzky still get run over by Suter in 1991 in this alternate reality? Because that changes a lot!