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Vaynerchuk Says He No Longer Cared About Yankees After 1996 Championship Win

Ed Mylett Show · Gary Vaynerchuk on AI, Self-Awareness, and Why Almost Everyone Is Pretending · June 23, 2026
Vaynerchuk Says He No Longer Cared About Yankees After 1996 Championship Win
Ed Mylett Show
Ed Mylett Show
Gary Vaynerchuk on AI, Self-Awareness, and Why Almost Everyone Is Pretending
"Yankees win in '96. Literally the next day, I didn't care about the Yankees anymore. And the same thing happened with the Rangers in '94. I've been a two-sport fan now for the last literally 30 years. Knicks and Jets. When the Red Sox won the 4th game against the Yankees that year, I was actually rooting for the Red Sox to come back from 3-0."
Gary Vaynerchuk revealed an unusual sports psychology quirk where he immediately lost interest in teams after championship victories, limiting himself to only rooting for perpetually struggling franchises. He admitted to rooting against the Yankees in the famous 2004 Red Sox comeback, demonstrating what he calls an 'underdog over everything' mentality that extends beyond rational fan loyalty.
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Ed Mylett Show
Ed Mylett Show

Gary Vaynerchuk on AI, Self-Awareness, and Why Almost Everyone Is Pretending

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