Since the draft cut off is around my birthday, I wonder about "what if" certain players had been born a day or two earlier/later.
Patrick Marleau (September 15th) - If he were born one day later, he would have been in the 1998 Draft. Coincidentally he might have still been drafted by San Jose, but then the Sharks probably would have ended up with Olli Jokinen in 1997 Draft en lieu of Brad Stuart + Jonathan Cheechoo in 1998. Marleau probably doesn't break the games played record if he had to wait another year to join the NHL.
Patrik Stefan (September 16th) - Born a day earlier and he's in the 1998 Draft. Does his career end up any better if he starts with Nashville or Vancouver instead of Atlanta? Brian Burke later told a story that he wanted to get both Sedins and Stefan in 1999.
Alexander Ovechkin (September 17th) - Comically Florida tried to draft him in 2003 on a technicality that the league denied. Panthers GM Rick Dudley knew he had a snowball's chance in hell, but figured it was worth a shot.
Auston Matthews (September 17th) - Do the stars align and Matthews ends up with the Coyotes if he were eligible in 2015?
Brady Tkachuk (September 16th) - Born a day earlier and he's in the 2017 Draft. Does he get into the conversation for the top pick?
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Maybe a slight tangent would be "what if" Rick DiPietro hadn't opted into the 2000 Draft? The Islanders would have proceeded (for at least a year) with Roberto Luongo, Olli Jokinen, and Marian Gaborik instead of DiPietro, Mark Parrish, and Oleg Kvasha.
And my favorite "almost trade" that I learned about in recent years was Quebec offering the rights to an unsigned Peter Forsberg to San Jose for the #2 pick in 1993. Quebec wanted Chris Pronger. Sharks GM Dean Lombardi fumed to the press afterwards implying he would have done the deal contingent on Forsberg signing. But since Quebec waited until the last minute, they had no time to talk to Forsberg's agent. The CBA was different in 1993 and there was no rookie salary cap plus Forsberg was about to get offer sheet rights. So San Jose couldn't risk trading the Pronger pick and having to give Forsberg a contract like Alexandre Daigle was about to sign.
But it's an interesting thought exercise with how things would have changed the next 15-20 years. How does Forsberg do in San Jose? Pronger in Quebec/Colorado? Mats Sundin maybe doesn't get traded and wins a couple Cups?