If you’re like me, someone who grew up with a special nostalgia for the Derek Jeter-era New York Yankees, then the ESPN documentary about his life and career The Captain was appointment viewing. And by appointment, I mean whenever I could get around to watching it.
That time finally came Sunday, and the first episode absolutely did not disappoint. The background on who the Yankees were pre-Jeter was enlightening. There was so much I didn’t know about the franchise I grew up rooting for.
One of those things was the lifetime ban Yankees owner George Steinbrenner received for his dealings with gambler Howard Spira – and how it was the likely catalyst for the dynasty they became. Digging into the situation a little more turned up how silly and avoidable the entire ordeal was, and I’m guessing I’m not the only one who wanted to learn more.
So here’s what happened.
Steinbrenner’s feud with Dave Winfield
It all starts with a feud between The Boss and Hall of Famer Dave Winfield, which included several legal battles between the two over the course of Winfield’s 10-year stint with the team. And it began almost immediately after Winfield signed his MLB-record 10-year, $15 million contract in 1980.
As told by former Yankees beat writer Joel Sherman, Winfield’s contract included cost-of-living kickers that could take the deal up to about $23 million. Apparently, Steinbrenner and his lawyers didn’t understand that part of the contract, which led to the Yankees owner feeling humiliated and growing contempt for Winfield before he even took the field in pinstripes for the first time.
Another part of Winfield’s contract required Steinbrenner to make annual $300,000 payments to the Dave Winfield Foundation, but he refused. That’s the root of at least one legal battle, and it’s also where Howard Spira comes in.
Who is Howard Spira?
In The Captain, the Yankees broadcast from when Steinbrenner officially stepped down described Spira as a gambler. The Bronx native has admitted as much. The truth is, for a gambler, he wasn’t a very good one. Spira once said he had to borrow $100,000 from his parents due to gambling debts with the mob.
Today in 1990, gambler Howard Spira was arrested for extorting money from Yankees owner George Steinbrenner, who paid Spira $40,000. Steinbrenner would be suspended because of his relationship with the unsavory caracter. pic.twitter.com/z80KpauX1x
— Baseball Reference (@baseball_ref) March 23, 2022
However, at the time of Steinbrenner’s feud with Winfield, his gambling was secondary to what he could do for the Yankees boss. Spira claimed to have worked as a publicist for Winfield’s foundation – Winfield’s people say that’s false – and he said he had dirt on the outfielder.
Committed to Winfield’s destruction, that’s all Steinbrenner needed to hear. In exchange for that information, Spira said Steinbrenner promised him $150,000, a job and residence at a hotel Steinbrenner owned.
Ultimately, Steinbrenner only paid Spira a total of $40,000 through two separate payments. But that would be the source of huge consequences for both once the payments were publicly revealed in March 1990. For his part, Spira was convicted in 1991 of trying to extort Steinbrenner. He served 22 months in prison.
In a Post story from 2010, Spira said Steinbrenner ruined his life.
Steinbrenner’s lifetime ban
Knowing how involved Steinbrenner was with the Yankees up until his death in 2010, it’s odd to hear about a lifetime ban. But he was, in fact, banned from day-to-day operations, forced to step away as managing partner and reduce his ownership to less than 50%. And it was actually a self-imposed punishment.
“By paying Mr. Spira, Mr. Steinbrenner placed himself at a minimum in the untenable position of having possibly financed the repayment of gambling debts or of bankrolling future wagering,” MLB commissioner Fay Vincent said at the time. “No participant in Baseball, let alone the owner of a Club, should put himself in such a position.”
Vincent said the misconduct didn’t warrant permanent expulsion, though. He wanted to suspend Steinbrenner for two years. But Steinbrenner didn’t want his punishment to be perceived as a suspension, according to the New York Times, so he opted for the more severe alternative of a permanent ban on his involvement in management and day-to-day operations. He was effectively giving the team up.
Though he was reinstated in 1993, Steinbrenner’s time away and subsequent appointment of Gene “Stick” Michael as general manager is credited for laying the foundation of a Yankees team that drafted and developed players like Jeter and won four titles from 1996 to 2000.
