When George Steinbrenner landed in hot water after handing out a $40K payment to a Yankees gambler
George Steinbrenner was the principal owner and managing partner of the New York Yankees from 1973 to 2010. In July 1990, Steinbrenner was banned from managing the team. This was because he had paid a Bronx gambler named Howard Spira a total of $40,000 to get damning information on right fielder Dave Winfield.
Winfield played for the Yankees from 1981-1988 and then again in 1990. Steinbrenner felt animosity toward the Hall of Famer because, according to writer Jim McLennan, "the owner never forgave the player or his agent for sliding a 'cost of living' increase into the terms of the contract, raising its cost from about $15 million to $23 million."
In the late 80s, Steinbrenner then tried to trade Winfield, but to no avail. Winfield was able to veto any trade. Steinbrenner then decided to sue Winfield's foundation for "misappropriation and misuse of funds," according to McLennan. Winfield, however, countersued Steinbrenner for failure to make promised payments to his foundation.
In retaliation, George Steinbrenner had Winfield investigated.
After banning the Yankees owner, baseball commissioner Fay Vincent said the following to the press:
"He did something to harm baseball and he has to pay the price," Vincent said.
He added:
"He knew, or at least should have known, that if the payment were exposed, it would bring disrepute to him and therefore to baseball."
Vincent finished with:
"No commissioner can permit or encourage an owner to run his own investigation into serious matters that are within the jurisdiction of this office, and baseball has long forbidden the kind of association with a known gambler that permeates this case."
As mentioned above, he was only banned from managing the team. However, he remained the owner of the team and left most of the daily baseball matters to other executives, especially Gene Michaels.
When Dave Winfield said he felt relieved by George Steinbrenner's ban
Dave Winfield and George Steinbrenner's strained relationship was well documented.
Many believed that it started when the Yankees signed the right fielder for 10-year, $23 million contract in 1980, making him the highest-paid player at that time. However, Winfield did not manage to play as per the expectations in the 1985 season.
This prompted Steinbrenner to say:
"Where is Reggie Jackson? We need a Mr. October or a Mr. September. Winfield is Mr. May. My big guys are not coming through. The guys who are supposed to carry the team are not carrying the team. They aren't producing. If I don't get big performances out of Winfield, Griffey and Baylor, we can't win."
As the strained relationship worsened, Steinbrenner even hired someone to find some dirty laundry on the player, which is what led to him getting banned. In response to the news of George Steinbrenner getting banned, Dave Winfield said:
"Personally, it's a weight off me. I've been trying to play ball (throughout this) 3,000 miles away. . . I feel somewhat vindicated."
The strained relationship with Yankees owner George Steinbrenner is why Dave Winfield entered the Hall of Fame with the San Diego Padres rather than the Yankees.