the fictionalized version of former Yankees owner George Steinbrenner, voiced by Seinfeld co-creator Larry David.
On Seinfeld, David's portrayal of Steinbrenner was played for laughs, but baseball fans know the real man was infamous for his quick temper. Under his watch, the Yankees had "championship or bust" expectations, which frequently led to massive turnarounds. In his first 23 seasons with New York, Steinbrenner changed managers 20 times, with Billy Martin being fired five times alone. Steinbrenner's penchant for firing people was the final punchline of the Seinfeld season 7 episode "The Wink," in which George's co-worker Mr. Morgan loses his job. Funnily enough, Steinbrenner's rambling turned out to be prophetic.
At the end of the episode, as George is leaving Steinbrenner's office, "The Boss" lists the various Yankee employees he fired over the years. The last name was then-Yankees manager Showalter. Steinbrenner catches himself mid-sentence and exclaims, "George! You didn't hear that from me!" "The Wink" originally aired on October 12, 1995. Showalter left the Yankees just a couple weeks later on October 26, 1995. When "The Wink" premiered, the Yankees had recently been eliminated from the MLB Playoffs, losing 3-2 to the Seattle Mariners in the ALDS.
The Seinfeld creative team obviously wasn't privy to any goings-on at the real Yankees organization. Showalter's name was included at the end as a joke commenting on Steinbrenner's tendencies. Still, it makes for a morbidly amusing turn of events, something akin to The Simpsons frequently predicting future events with eerie accuracy. If anything, the gag was probably originally conceived as a playful jab at the Yankees manager, who made a guest appearance as himself on the Seinfeld season 6 premiere, "The Chaperone." No one involved with Seinfeld has commented on the prediction, though Showalter has mentioned he still gets taxed for his role on "The Chaperone."
Showalter was replaced by Joe Torre, who oversaw a Yankees dynasty. During Torre's tenure, New York won four World Series and clinched six American League pennants between 1996-2003. Sadly, a majority of this run came after Seinfeld wrapped up after 9 seasons (and George had already left his job with the Yankees), so the show couldn't work New York's three-peat into some episodes. It would have been interesting to see how Seinfeld tackled the Yankees becoming the most dominant team in baseball, but at least they had some fun before g off the air.
Seinfeld is now streaming on Netflix.