On September 19, 1968 at Tiger Stadium, Detroit right-hander Denny McLain was cruising along in the top of the eighth with a 6-1 lead over the New York Yankees. He had won his 30th game five days earlier, and the Tigers had already clinched the American League pennant. When Yankee first baseman Mickey Mantle came to bat with one out and nobody on, McLain let Mantle know that he would give him whatever pitch Mickey wanted. Mantle signaled for a fastball letter high, McLain delivered it, and Mantle hit it into the right field seats for his 535th career home run. Although McLain was coy after the game in the locker room, everyone knew what had happened.

It was classic McLain: charming, cocky, arrogant, reckless. A rebel or a punk, take your pick, and your choice likely depended on your age and your politics. Just 24 years old, McLain had played by his own rules his whole life, and as the first 30-game winner in baseball in 34 years, he could get away with just about anything. He knew it. He had a prickly relationship with his teammates, managers, and the fans, all of whom he was apt to criticize in the press. Bill Freehan, his catcher, once wrote, “The rules for Denny just don’t seem to be the same as for the rest of us.”

On the mound, he was a gunfighter. He pulled his hat brim down so low that he had to cock his head upwards to see the signs from his catcher. He worked fast and without deception. He used fastballs and hard sliders for the most part, challenging the hitter with every pitch. If a batter hit the ball hard, the next time up McLain would give him the same pitch in the same location.

Off the field, McLain’s life was equally carefree and, it would turn out, even more reckless. His idol was Frank Sinatra, not so much for his singing voice but because he exuded wealth and power. He was an accomplished organist–he played the Ed Sullivan Show, headlined gigs in Las Vegas, cut a few records. He flew his own airplane.

In 1969 McLain and Pete Rose co-authored an instructional booklet called “How to Play Better Baseball.” The project likely did not require that Rose and McLain get together to work on the book, which is unfortunate. If they had, they would have discovered that they had a lot in common.

McLain won the Cy Young Award, MVP, and the World Series in 1968, and won the Cy Young again in 1969 when he won 24 games. He made $100,000 from the Tigers, and at least that much off the field. He seemed to be living the dream life. And suddenly, he wasn’t.

In February 1970, Sports Illustrated broke the story of McLain’s off-field woes. According to the magazine, in early 1967 McLain invested in a bookmaking operation based out of a restaurant in Flint, Michigan; many of his partners were part of the Syrian mob. When a gambler named Edward Voshen won $46,000 on a horse race in February 1967, his bookie couldn’t pay it off, suggesting instead that Voshen find the bookie’s partners. One of his partners was McLain. Voshen spent several months trying to get his money, finally enlisting the aid of mobster Tony Giacolone. According to the magazine’s sources, Giacolone met with McLain in early September and, while threatening much worse, brought his heel down on McLain’s toes and dislocated them.

McLain had, in fact, hurt his foot in September 1967. After several poorly pitched games–no wins, two losses, 13 runs allowed in 13 2/3 innings over four starts–McLain reported that he had severely injured two toes on his left foot. His foot had fallen asleep while he was watching television, and he stubbed it when he got up. No, wait a minute, he hurt his toes chasing raccoons that were getting into his garbage cans. Uh, actually he kicked a water cooler (or was it a locker?) after getting removed from a game. Anyhow, he did not pitch again for 13 days, until the very last game of the season. If Detroit had won, the club would have forced a one-game playoff with the Red Sox for the American League pennant. Unfortunately, McLain was again ineffective, and the Tigers lost to the Angels to fall one game short.

SI also reported that Giacolone had bet heavily on the Red Sox and Twins to win the pennant, and had made a large bet on the Angels in McLain’s final start.

McLain denied most of the story. He admitted to investing in the bookmaking business, to the tune of $15,000, but claimed that his partners reneged on him, causing McLain to withdraw his support. He told Bowie Kuhn, baseball’s commissioner, that he was completely uninvolved in the ring at the time of the Voshen bet, but oddly admitted that he had loaned $10,000 to one of the partners to help pay off the debt. Furthermore, he had never met Giacolone, and McLain repeated that he had hurt his toes first by stubbing them at night when his foot was asleep, and then by kicking a locker. Just prior to spring training, Kuhn suspended McLain while he conducted an investigation.

To be fair, the problem with all of these accusations was that many of the people making them were criminals and lowlives, as SI acknowledged. This problem also exists in the Pete Rose imbroglio: Since virtually all of Rose’s associates seemed to have been losers with rap sheets, it is hard to find a credible witness.

Without his baseball income, McLain’s financial problems caused him to file for bankruptcy. Claiming that all of his problems were due to “poor business decisions,” his petition listed debts of $446,069 and assets of $413.

Kuhn did not investigate McLain’s mess himself, of course. The case was handled by Henry Fitzgibbon, a former FBI agent recently hired to run baseball’s new security office. Fitzgibbon and his staff were to keep abreast of players’ off-field problems, specifically those involving drugs and gambling. McLain was the staff’s first big investigation. (Their second one involved Rose, whose gambling problems raised red flags for baseball as early as 1970. Fitzgibbon suspected for many years that Rose bet huge sums of money with bookmakers, which Rose almost certainly did, but Fitzgibbon was never able to catch him. The bookies, of course, were not talking.)

In considering McLain’s punishment, Kuhn had a long history to draw upon. In addition to the eight players barred for conspiring to fix the 1919 World Series, many other players and officials had been punished over the years for gambling-related offenses. In 1947, commissioner Happy Chandler suspended Dodger manager Leo Durocher for the season, mainly because Durocher ran around with the likes of gangsters Bugsy Siegel and Joe Adonis. Durocher had not been accused of doing business with these men, only of socializing with them.

On April 1, 1970, Kuhn announced his decision. He continued McLain’s suspension until July 1, roughly half of the season. Kuhn’s report, among other things, said: “While McLain believed he had become a partner in this operation and has so admitted to me…it would appear that he was the victim of a confidence scheme. I would thus conclude that McLain was never a partner and had no proprietary interest in the bookmaking operation.” Kuhn also absolved McLain from any charges that his actions had any effect on baseball games or on the 1967 pennant race.

After Kuhn read his statement, a reporter asked him to explain the difference between McLain attempting to become a bookmaker, and actually becoming one. In a classic reply, Kuhn answered, “I think you have to consider the difference is the same as between murder and attempted murder.”

(It is interesting to compare Kuhn’s decision in 1970 with one he made in 1979, disallowing Willie Mays from working for the Mets because he took a job doing publicity for Bally’s casino in Atlantic City. Four years later, Mickey Mantle took a similar job at a different casino and was required to sever his ties with the Yankees.)

Reporters all over the country, and especially in Detroit, thought the decision was a whitewash. McLain’s teammates seemed surprised as well. Dick McAuliffe spoke for many when he said: “If Denny’s innocent, it should be nothing. If he’s guilty, then this is not enough.” Jim Price, the Tigers’ player representative, said that most Tigers thought McLain would get one or two years, or else nothing at all. Nonetheless, three months it was.

McLain returned on July 1 to a packed house, but struggled that night and for the next several weeks. On August 28, he doused two Detroit writers with buckets of ice water, earning him a seven-day suspension by the club. Before the week was up, commissioner Kuhn discovered that McLain had carried a gun on a team flight in August, so he was declared ineligible for the rest of the season. His 1970 record was 3-5 with a 4.63 ERA.

A few days after the season, McLain was traded to the Senators in an eight-player deal. Although he was just 26 years old and was six months removed from being considered one of the best players in the game, the Tigers considered themselves fortunate to acquire pitchers Joe Coleman and Jim Hannan and infielders Aurelio Rodriguez and Eddie Brinkman for him.

They were fortunate indeed. In his one year in Washington, McLain carried on a yearlong battle with manager Ted Williams, and finished 10-22. He spent 1972 with the Oakland A’s, the Birmingham Barons, and the Atlanta Braves, getting hammered at all three stops, before finally drawing his release by the Braves the next spring. McLain claims to have suddenly lost his fastball in 1970, but one couldn’t help but notice that he was putting on 10 pounds of fat per year. At the time of his release, he was 29 and looked 45.

Without his baseball career to get in the way, McLain could now devote all his energies to his “successful” business ventures. Always looking for the fast buck, he invested in a big screen television business, ran a bar, wrote a book, and opened a line of walk-in medical clinics. In the mid-’70s he was the general manager of the minor league Memphis Blues, who soon went belly up. McLain filed for bankruptcy again in 1977.

He made a living for a while by hustling on the golf course. While involved with a financial services company in Tampa, he turned to loan sharking and bookmaking. With losses piling up, he and his colleagues got more adventurous. He once made $160,000 smuggling a fugitive out of the country in his airplane.

Eventually, the U.S. Justice department began to sniff around McLain’s associates, several of whom were willing to talk. In March 1984, McLain was indicted on charges of racketeering, extortion, and cocaine trafficking. He was tried, convicted, and sentenced to 23 years in prison. Thirty months later, an appeals court threw out the verdict on procedural grounds, setting McLain free, with the government eventually deciding not to retry the case.

McLain spent the next several years putting his life back together. He wrote another book, appeared at card shows, worked for a minor league hockey team, and got his own radio show. He was doing what he could have done all along–making a living being Denny McLain. It was a good living, reportedly $400,000 a year.

It wasn’t enough. In 1993 he and a friend bought Peet Packing, a struggling 100-year old meat packing firm in Chesaning, Michigan. Within a month after the sale, $3 million was taken from the company’s pension fund, and by 1995 the company was bankrupt. McLain and his partner were eventually convicted on charges of embezzlement, money laundering, mail fraud, and conspiracy. In 1998, McLain was also named (along with John Gotti, Jr.) in an indictment on charges involving bogus telephone calling cards, though those charges were eventually dropped.

Nonetheless, McLain began serving his eight-year sentence for the other charges in 1996, and has since spent much of his time denying that he did anything wrong, while trying to get his conviction thrown out. His wife, the most loyal woman on this planet, finally left McLain on the day he returned to prison.

The scary question to ponder about McLain is this: if he had not lost his pitching ability so rapidly in the early 1970s, how and when would he have self-destructed? It is not likely that McLain could have negotiated all of his land mines for 10 or 12 more years, is it?

This is a man who was involved in bookmaking, the trafficking of fugitives, and narcotics at an age when he might still have been winning baseball games. It’s easy to suppose that he would have just put off a life of crime for another decade while his career wound down. But this was not McLain’s style. His life as a well-compensated hero was never enough for him. More likely, he would have continued to try to balance his duel passions–baseball and organized crime–and at some point the two would have crashed together.

When McLain got in hot water in 1970, Bowie Kuhn’s big concern was whether he had bet on baseball games. Getting involved with a mob crime ring was one thing; putting a hundred bucks on the Astros was the bigger problem. Kuhn found no evidence that McLain was gambling on baseball, so he gave him a fairly light sentence.

McLain admitted to wagering large sums on other sports, but claimed that he never placed a bet on baseball, either during or after his career. Can you imagine? We are to believe that a man who was comfortable trafficking in narcotics and stealing from a retirement fund, could not bring himself to gambling on a baseball game? What stopped him exactly? He didn’t want to damage the game he loved? What about the damage he did to his wife and children?

Baseball has a paranoia about gambling, a paranoia that is fully justified. Let’s face it: The nature of gambling, for the most part, is that you end up losing a lot of money. The people that you owe that money to tend to be unforgiving sorts, and there are no safe places to turn without having to answer a lot of uncomfortable questions. At a 1978 meeting of Reds’ executives, general manager Dick Wagner reportedly said, speaking of Rose, “Pete’s legs might get broken when his playing days are over.” In McLain’s case, his friends might not have even had the decency to wait for his retirement party before breaking body parts.

How hard is it to imagine McLain fixing a game? Here is a man who has shown himself to be willing to do anything imaginable, no matter how ethically repugnant, to make a few bucks. He took $160,000 to transport a criminal out of the country. Why not throw a few fat fastballs to Reggie Jackson–that’s a hell of lot easier, isn’t it? He threw one to Mantle in 1968, and everyone got a big kick out of it. How hard would it be to throw a baseball game? For a manager, it might get a little messy, but for a starting pitcher, the right pitch with men on base could all but put the game in the bag.

Baseball dodged a bullet with McLain. Because of a bad arm or too many fatty foods he was not in a position to inflict too much damage to the game. Bowie Kuhn believed that poor Denny fell in with the wrong crowd and was fortunate to have been double crossed before he got in too deep. As the list of felonies for which he has been convicted approaches double digits, we might now pity those poor saps who fell in with him.

Thank you for reading

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One very minor correction to the above. In 1969, he was co-winner of the Cy Young Award, along with Mike Cuellar. Sadly (at least for Cuellar), one voter completely left him off the ballot, while voting for Dave McNally, his teammate and fellow lefty.