What's the most impactful flip that would've changed the course of history if results reversed?

not a flip but I remember Duhamel sucking out with JJ vs AA on a 9TQ flop I think in the main event

I had action so it was a good day

Must have been some of Stu Ungar's hands 1997.

Didn't Mike Matusow in 2005 and Allen Cunningham in 2006 bust out in coin flips at the Main event final table?

I think mike lost with Pocket Tens against Steve Dannenman's AK.

Daniel Negreanu also busted against Joe McKeehen in 2015 right before the final table.

Superman crash landing in the US as a baby, instead of landing in Nazi Germany.

super bowl LI overtime toss

Red Son

This is gold....

There also is some "fan fiction" online about "Uberman", the result of Superman landing in Nazi Germany as a child, but it is not well done in my opinion.

If Jesus was a woman

Doyle asking for help unloading the sheetrock.

greenstein vs dwan 50/50 on the flop flip for a million dollar pot.
it was one of the hands that made dwan a legend also greenstein lost a major chunk of his roll in this hand. very significant moment in both players careers.

Raymer in 2005 vs Aaron Kanter donk turn. If Kanter doesn’t hit the heart on the river, Raymer would have had 10% of the chips in play with 3 tables left. Final Tabling or even winning that probably GOATs him. Peak eyeballs were on those two years and he would have made a killing on sponsorships.

Trump vs Clinton?

This is a great one

It wasn’t a “flip” but yes. Has to be number one.

It's not even close to that impactful. Let's say Raymer wins that flip, what changes:

Most likely he still doesn't win - there's still a bunch of people to get through. Probably finishes on the final table.
Poker boom continues
Raymer gets somewhat richer - not as rich as he imagines but richer. The only real difference is if he wins, I suspect he makes outrageous demands from PokerStars, and gets shot down by Isai. He moves on to another site instead that thinks he's worth it.
Joe Hachem is just a random mid 2000s final table finisher unless he wins, in which case he signs the same deal with PokerStars that he already did

That's it.

With that said, I'm not sure I have an alternative other than maybe Moneymaker vs Ivey AQ vs 99 (even though I understand all money didn't go in preflop). Moneymaker boom isn't quite as big, but the legend of Ivey goes thermonuclear.

Bush Gore

Had Gavrilo Princip missed.

Or gone out for a burrito rather than a sandwich.

I saw one of those - my old buddy CB Trujillo flopped a wheel - bet, raise, money goes in on the flop. Stuey had 2pair hit the full on the river. Stuey kind of thought about calling the all in but not too long.

You were railing, incredible! Was the hand indoors or outdoors?

Indoors at Binions, railing allowed - no big crowds watching in those days.

negreanu vs coleman all-in A4 vs KQ has to be one too. negreanu doesn't win if he wins the flip but it'd make him very live in what was the biggest tournament ever at the time.

Moneymaker's 88 against AA, hits the two outer.