In the fall of 1967, in the middle of a tight pennant race with the Boston Red Sox, the Detroit Tigers’ 23-year-old flamethrower Denny McLain, a 17-game winner through August, badly injured two toes on his left foot. McLain, who claimed he had stubbed his toes after his foot had fallen asleep while watching television, missed a few key starts before returning to lose the final game of the season as the Tigers fell one game short of the Red Sox.

McLain rebounded the following season to become baseball’s first 30-game winner since 1934 (and likely its last), going 31-6 and earning MVP and Cy Young honors. The Tigers won the World Series and McLain, on the verge of a storybook career, truly seemed to have it all — if by “have it all” you also meant massive debts, gambling problems and mob ties. Then the roof came crashing in on Denny McLain in February 1970, when Sports Illustrated published a cover story — under the headline “Downfall of a Hero” — about his off-the-field entanglements, including the claim that the true source of his dislocated toes was the punishing heel of mobster Tony Giacalone. (McLain did not respond to requests for comment but has repeatedly denied the allegation.)

McLain lost more than money that season. He lost his fastball and his career.

“A self-admitted hustler, McLain was always looking for a big deal,” writes Daniel E. Ginsburg in The Fix Is In, “a way to make easy money.” Born on Chicago’s South Side, he was a numbers runner for gamblers by the age of 15, and after his hometown White Sox signed the right-handed pitcher with a devastating fastball for $17,000 in 1962, McLain immediately went out and purchased two Pontiac LeMans — a convertible for himself and a hardtop for his mom. Later picked up by the Tigers, the young hurler was always looking to make a quick buck. Even after winning the World Series in 1968 and signing a six-figure deal with the Tigers, McLain took an off-season gig playing the organ — another of his many talents — at a Las Vegas Hotel.

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On the mound, McLain, his hat brim pulled down low, was cocksure and fearless, challenging hitters with a steady diet of fastballs and sliders. In 1966, his first full season in the majors, the 6-foot-1, 190-pounder won 20 games. The following year, according to the SI story, McLain invested in a bookmaking operation in Flint, Michigan. When one of the bookies failed to make a large payoff to a gambler named Edward Voshen, the story said, he sent Giacalone after McLain to collect. Baseball commissioner Bowie Kuhn sprung to action in response to the article, enlisting a former FBI agent to investigate the allegations against the game’s best pitcher. On April 1, 1970, Kuhn regrettably announced that McLain would be suspended for three months for his connection to the operation, even though he claimed McLain “had no proprietary interest in the bookmaking operation” and his actions did not affect any baseball games.

Denny

In 1966, his first full season in the majors, pitcher Denny McLain won 20 games.

Source: Getty

With no baseball income coming in for those months, McLain was forced to file for bankruptcy due to “poor business decisions.” “I was not quite 26 years old,” McLain later observed in his first autobiography. “I was making at least $150,000 a year [but] … the F.B.I., the Internal Revenue Service, the commissioner of baseball, 86 creditors, and a few other vultures were on my back. … I owed more than $446,000!”

McLain lost more than money that season. He lost his fastball and his career, going just 3-5 in 14 games while incurring further suspensions for dumping ice water on two reporters and carrying a gun on a commercial flight. After the season, he was traded to the last-place Washington Senators, where he led the league in losses with 22 in 1971. He was out of baseball by 1973.

But life for the fallen pitcher hardly slowed down after he left the game. Among many other things, McLain opened a chain of walk-in medical clinics, played baccarat in Atlantic City and did commercials for local car dealerships. He was also given a suitcase filled with $160,000 for helping smuggle an accused criminal out of the country to avoid prosecution.

McLain was less adept at avoiding prosecution himself. In 1984, he was indicted on charges of racketeering, extortion and cocaine trafficking, and sentenced to 23 years in prison, a verdict that was later thrown out on procedural grounds. A decade later he was back in the slammer for embezzling from the pension fund of a meat-packing company he had set up with a partner. He served more than six years before being released in 2003.

These days, McLain, 71, is still busy, making a few bucks doing public appearances and promoting his two books, Nobody’s Perfect and I Told You I Wasn’t Perfect. “Everyone has a story,” McLain reflects in the latter, “and all of us have experienced some kind of hell in our lives.” True, but few people — in or out of baseball — will ever experience the perfect hell that Denny McLain made of his life.