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Caridi told SI in August that Spira was a "degenerate gambler" who hung around a Long Island restaurant Caridi used to run. Two sources familiar with Colombo family operations told SI last week that in the early 1980s Caridi, aware that Spira was close to Winfield and was, in the words of one of the sources, "betting all over the place," decided to start taking wagers from Spira. One of the sources said that Caridi "wanted to get next to the Yankees" and figured that Spira would be able to help him do that. The source said that Spira soon ran up large gambling debts to Caridi. The two sources describe this scene in which Spira and Caridi rode through Manhattan in Caridi's limo:
Spira owes Caridi $57,100, and Caridi is demanding payment. Spira reaches into his pocket and pulls out a baseball signed "To Anthony from Dave Winfield." Anthony is Caridi's son. Spira then pulls out a couple of glossy photos of Winfield signed the same way. Caridi tosses those offerings aside and again demands his money. "I'm a little short," Spira replies. "Well, I think I could borrow the $100. But I can't get you the $57,000." Caridi grabs Spira by the front of the shirt, lifts him up through the limo's sunroof and partially closes the roof, leaving Spira's head sticking outside the car.
One of the sources said that Caridi and Spira later agreed that Spira would gradually pay off the debt and that Caridi would keep Spira's other bookmakers at bay. Why Caridi would offer Spira such a deal is not known. Steinbrenner says, "It astounded me that anybody could owe bookmakers that much money. I was concerned that [Spira] was passing on information to the people that he owed money to. They [organized crime] didn't want to cut off their source into the New York Yankees. If it was one of their own, he would have been in the river." A source with knowledge of organized crime activities said Caridi never succeeded in getting "next to the Yankees."
Spira was deep enough into organized crime that according to two sources familiar with the situation, the FBI offered in 1986 to pay him $100,000 and put him into the federal witness protection program if he would testify against mob figures. Spira turned down the offer, but the fact that the FBI wanted to use him as a witness suggests that federal investigators put more stock in his credibility than baseball did.
While baseball continued to discount what Spira had to say, it was unbothered by the questionable veracity of Winfield. On Jan. 10, 1989, Spira went public with his claim that Winfield had lent him $15,000 in December '81. Spira said he had needed the money to pay off sports gambling debts. "Give me a break," Winfield told the New York Daily News when asked about the allegation. "I never gave him any money." Spira later produced a photocopy of the check, which was reprinted in newspapers. Winfield then acknowledged that he had indeed made the loan, though he said he couldn't remember what the money was for.
The day after the Daily News story, baseball issued a press release: "The Office of the Commissioner has been aware of the charges raised by the New York Yankees about the possible involvement of Dave Winfield with an individual who allegedly has participated in sports betting. To date evidence has not been presented or uncovered which would warrant Commissioner action. We will continue to investigate the matter."
In truth, baseball was conducting no such ~investigation. Hallinan said in sworn testimony given in the Steinbrenner case that baseball's use of the word investigation "may have been a misstatement."
It was only after Spira started pestering the commissioner's staff, claiming that he had damaging information about Winfield, that Hallinan finally interviewed Spira, on Feb. 15, 1989. According to a transcript of that interview, Spira asserted that Winfield had been aware of Spira's gambling on baseball games, including Yankee games, during the early '80s and had regularly discussed the subject with Spira. "I never, never said, nor did anybody ever ask me to ask Dave to throw a game, get a hit, strike out—I'll make that very clear," said Spira in the interview. But then he added that Winfield "always wanted to know which side I was betting" on in baseball games, including Yankee games. Spira said he had bet $1,000 or more at a time, often calling his bookies from the Winfield foundation offices.
Spira also told Hallinan that Tony Dill, a producer for NBC News and a friend of Spira's, had heard Winfield mention Spira's gambling debts while Winfield was preparing for a taping of NBC's Tomorrow show in December '81. Dill told SI that Spira introduced him to Winfield backstage and that Winfield was kidding Spira about the debts. "Dave knew Howard was gambling," Dill said. "Anybody who Howard got to know would know about his gambling."
During Hallinan's questioning of him, Spira also alleged that Whitton had placed bets for Spira on the 1981 Series. "All I'll say about this Al [Whitton] is I know he had heavy ties with a guy named Little Al [Grecco] in the Genovese crime family. And he was making the bets for me," said Spira. Whitton has admitted to SI that he hooked Spira up with at least one bookmaker in the early '80s, but he denied that he had placed World Series bets for Spira. Grecco is currently in jail awaiting trial on federal charges of murder, extortion and gambling. Grecco's indictment identified him as head of the Genovese family's New York and New Jersey sports gambling operations.