"He's the original flim-flam man. Any day I expect him to come riding on a Conestoga wagon selling elixir out the back end as he's leaving town. Probably being run out of town. But that's Denny," says former Tigers teammate Jim Northrup about Denny McLain on ESPN Classic's SportsCentury series.

Denny McLain will be remembered for two things: He was the last 30-game winner of the 20th century and that he spent a lot of time in prison. His off-field activities as a player and his post-retirement involvement in a string of felonies have cast long shadows over the Detroit Tigers righthander who dominated the American League in 1968 when he became the first pitcher in 34 years to win 30 games.

Recording a 31-6 record with a 1.96 ERA, he earned MVP and Cy Young honors. His 280 strikeouts - as opposed to only 63 walks - also contributed to Detroit's first pennant since 1945. At 24, McLain seemed to have it all.

But within 16 months, McLain's image was badly tarnished. In February of 1970, Commissioner Bowie Kuhn suspended him until July 1 for bookmaking activities, one of three suspensions he was hit with that year.

Life after baseball also proved troublesome to McLain. In the mid-eighties, he spent 27 months in prison after convictions on federal racketeering charges involving gambling and cocaine. A decade later, McLain was back in prison for looting a company's pension fund. He's not scheduled for release until 2004.

McLain was born on March 29, 1944 on Chicago's South Side and was raised with his younger brother Timmy in the Chicago suburb of Markham. Denny played his way onto Little League and Babe Ruth League teams from other towns because Markham didn't have organized leagues. He starred - as both a pitcher and shortstop - at Chicago's Mount Carmel High School, leading the school to back-to-back Catholic League championships in his junior and senior years.

During his freshman season in the spring of 1959, perhaps the most traumatic event in McLain's life occurred: the death of his father Tom. His father was his inspiration - both in baseball and in playing the organ.

McLain signed with the Chicago White Sox for $17,000 after graduating from high school in 1962, but was claimed by the Tigers organization on first-year waivers the following spring. He was brought up late in 1963 and went 2-1 with Detroit. A few days after the season ended, he and Sharyn Boudreau, the daughter of Hall of Famer Lou Boudreau, eloped to New Buffalo, Mich.

In 1964 McLain was farmed out to Syracuse of the International League but was called up in late May. In an injury-ridden season, he went 4-5. The following year he came into his own, going 16-6 with a 2.61 ERA as he learned to throw a curveball and changeup to go with his outstanding fastball.

During this time, McLain also learned another thing. His manager, Charlie Dressen, taught him how to handicap horses, a skill that exacerbated a lifelong obsession with gambling. What McLain picked up on his own was his womanizing, another lifelong obsession. He and Sharyn separated several times before they divorced in 1998.

Despite arm problems, the 6-foot-1, 185-pound McLain soared to the verge of stardom, going 20-14 with a 3.92 ERA in 1966 and 17-16, 3.79 in 1967. During the latter season, McLain raised some eyebrows when he missed the last two weeks in September because of a mysterious foot injury while Detroit was involved in a heated pennant race.

But it was 1968 that put McLain's name in the record book. By the All-Star break, he was 16-2. Besides his 31 victories, he led the American League by completing 28 of his 41 starts and pitching 336 innings as he became the first 30-game winner in the majors since Dizzy Dean in 1934.

While McLain went 1-2 in the World Series, losing twice to the Cardinals' Bob Gibson, the Tigers won in seven games, with Mickey Lolich picking up the slack with three victories. Almost immediately after the Series, McLain accepted a gig playing the organ at a Las Vegas hotel.

In 1969, McLain again led the AL in victories, going 24-9 with a 2.80 ERA, and shared a second Cy Young prize, with Baltimore's Mike Cuellar. But that season brought trouble in the clubhouse. McLain clashed with manager Mayo Smith over the latter's role in getting pitching coach Johnny Sain fired. McLain showed his displeasure by missing workouts between starts and arriving at the park only shortly before game time.

The next year, 1970, was an outright disaster for McLain - and the beginning of the end of the road for his baseball career. Kuhn suspended McLain after Sports Illustrated detailed the pitcher's role in a bookmaking operation in Michigan during the 1967 season.

McLain injured his toes that September; he gave different descriptions of how the accident happened. The Sports Illustrated story offered another possible version: A member of the mob brought his heel down on McLain's toes and told him to pay a $46,000 bookmaking debt.

In late August 1970, McLain dumped ice water on two reporters and the Tigers suspended him. Then in September Kuhn told McLain he would not be allowed to pitch the rest of the season because the pitcher carried a gun - he waved it in a Chicago restaurant - and violated the terms of his probation.

That year, McLain also applied for bankruptcy despite his having become the franchise's first $100,000 player after the 1968 season. He had lost not only his money but his fastball as well. Appearing in only 14 games, he could do no better than a 3-5 record.

It came as no surprise when he was traded after the season, being sent to the last-place Washington Senators. McLain and manager Ted Williams developed a mutual animosity. By losing 22 games (against only 10 wins) in 1971, McLain earned the distinction of falling from the league lead in victories to the league lead in losses in just two seasons.

In 1972, McLain was traded twice, to the Oakland A's and then the Atlanta Braves. His combined record was 4-7 with a 6.39 ERA.

He tried to make a comeback the following year, in the minors with Des Moines and Shreveport, but the fastball wasn't there anymore and neither was the desire. McLain finished his major league career with a 131-91 record and 3.39 ERA.

He tried a number of jobs after leaving baseball. None succeeded for long. Among McLain's other "careers" were as promotions director for a minor league hockey team and a plan to buy a South Carolina radio station. The former ended when he was fired over a problem with the team budget, the latter when his partners won a suit to get their money back.

He played the organ in a variety of cocktail lounges, cut an album, and opened his own place called Gaffner's that failed in a short time. One job was playing synthesizer in a Detroit bar where former heavyweight champion Leon Spinks was a greeter-bartender. McLain's weight shot up to more than 300 pounds.

After moving to Lakeland, Fla., he became a partner in First Fidelity Financial Services, rumored to be backed by the Mafia. In 1985, McLain was found guilty of federal charges involving racketeering, extortion and narcotics and sentenced to 23 years. In 1987, his convictions were overturned due to procedural violations. When the government re-indicted him, he pleaded guilty. He received a 12-year sentence, but the feds let him off with five years probation and time served, so he was free.

Returning to Detroit, McLain was a hit as a radio talk-show host. That wasn't good enough for him.

In 1994, he and some associates bought a Chesaning, Mich., meat-processing company that went bankrupt two years later. He and an associate were indicted for looting the company's pension fund of $12.5 million. Convicted in December 1996 of conspiracy, theft, money laundering and mail fraud, he was sentenced to eight years.

McLain served more than six years in the McLean Federal Correctional Institution in Bradford, Pa., until he was released in 2003 and transferred to a halfway house in Detroit for six months. During that time, he was employed in a 7-Eleven. He is on supervised release for three years, during which he must remain in regular touch with his probation officer.