When George Steinbrenner's resentment of Dave Winfield destroyed his reputation as an owner

George Steinbrenner and Dave Winfield have had a tense friendship. When Steinbrenner signed the outfielder on a ten-year contract as a free agent in 1980, the 29-year-old was already a four-time All-Star and became the highest-paid player in the game.

However, The Yankees owner never forgave the player or his agent for adding a "cost of living" adjustment to the contract's provisions, increasing its cost from around $15 million to $23 million.

In 1985, Steinbrenner, who frequently criticized Winfield, said:

"I let Mr. October get away, and I got Mr. May, Dave Winfield. He gets his numbers when it doesn't count."

Baseball Commissioner Fay Vincent opened up about the rivalry:

"It was a pretty sordid and unattractive story of George trying to destroy Dave Winfield. It was not Steinbrenner at his best."

After the 1980s, things became quite unpleasant. Steinbrenner tried to trade Winfield, but his position as a 10-and-5 person (ten years in the majors, five with the same team) gave him the power to block any deal, which hindered Steinbrenner's efforts.

Even though Winfield played much longer in the Bronx and hit 51 more home runs there than in San Diego, Steinbrenner and Winfield finally reconciled.

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When George Steinbrenner handed out a $40K payment to a Yankees gambler

George Steinbrenner and Dave Winfield

From 1973 to 2010, George Steinbrenner served as the New York Yankees' major shareholder and managing partner.

Steinbrenner was prohibited from overseeing the team in July 1990, though. That was due to the $40,000 he had spent on Bronx gambler Howard Spira to obtain damaging information about right fielder Dave Winfield.

Winfield participated in two more seasons (1988 and 1990) with the Yankees. According to author Jim McLennan, Steinbrenner harbored resentment towards the Hall of Famer because of the aforementioned 'cost of living' expenses.

Steinbrenner attempted to transfer Winfield in the late 1980s, but his efforts were unsuccessful, as any trade was subject to Winfield's veto. After that, Steinbrenner filed a lawsuit against the Winfield Foundation for "misappropriation and misuse of funds".

However, Winfield countersued Steinbrenner for failing to make the payments he had agreed to make to his foundation.