The Disgrace of Denny McLain, Baseball’s Last 30 Game Winner

Detroit Tigers Hurler was Suspended for Gambling, Later Served Time for Racketeering & Embezzlement

Jon Hopwood
12 min readSep 7, 2020
A John Weeks “Mr. Baseball” Memorial Review of the History of Baseball

The 50th anniversary of Denny McLain’s monumental 30-game winning season of 1968 wasn’t honored. Neither was the 60th anniversary.

Before the short COVID-19 season of 2020, some baseball pundits predicted that we might see the first .400 hitter in over three quarters of a century, when Ted Williams hit .406 in 1941. That’s not likely to happen, though a .400 hitter is not outside the realm of possibility in the future.

What is outside the realm of possibility, perhaps forever, in a baseball world of five-man rotations and Cy Young Award winning starting pitchers with all of 10 victories is the 30-game winner.

The Year of the Pitcher

In a year when America was racked by race riots in the wake of the assassination of the Rev. Dr. Martin Luther King, Jr., 1968 was the “Year of the Pitcher.” In that season, only one batter in the American League, future Hall of Famer Carl Yastrzemski, hit over .300. Yaz, the defending A.L. Most Valuable Player, hit all of .301, the lowest average ever to top the junior circuit. Yaz lost his MVP crown that year to Denny McClain, the first pitcher to notch 30 wins since Dizzy Dean in 1934 and the last 30-game winner in baseball history. McLain also garnered the Cy Young Memorial Award as best pitcher in the American League.

So momentous was Denny McLain’s achievement, that it overwhelmed the regular season performance of future first ballot Hall of Famer Bob Gibson in the Senior Circuit, who had an Earned Run Average of a 1.12. For his outstanding season, Gibson likewise won MVP and Cy Young honors. Gibby’s ERA led both leagues and harkened back to the Dead Ball Era of the pre-Babe Ruth 20th Century. (Gibby threw an amazing 13 shutouts in 1968. In three of his nine losses, he gave up just one earned run, and he surrendered just two earned runs in three other losses. He had a 2.14 ERA in his nine losses and would have racked up a 30–2 record had the Cardinals plated four runs in each of his starts that year.)

McLain and Gibson would face off in the 1968 World Series.

Denny McLain helped his Detroit Tigers dethrone Bob Gibson’s St. Louis Cardinals, the defending world’s champions, though he lost the first two games he pitched in. Game One, the Series opener, matched him against Gibson.

Gibby, supposedly enraged by all the media attention McLain got by winning 30, and believing himself the better pitcher, opened the Fall Classic by fanning a record 17 batters while posting a game-winning, five-hit shutout. Gibby would establish a World Series record of seven straight wins, dating back to the 1964 Fall Classic when the Cards beat the New York Yankees, by also winning Game 4, putting the Tigers on the brink of elimination.

In Game 4, Gibby beat McLain again, surrendering just one run in nine innings, and hitting a home run off his American League nemesis.

Future donut shop-owner and Game 2-winner Mickey Lolich, who sported a large donut if not rubber tire around his midsection, staved off elimination by winning Game 5 for Detroit, and subsequently, Denny McLain kept the Tigers’ hopes alive when, on two days rest, he beat the Cards in Game 6.

McLain scattered nine hits, surrendering just one run in the ninth. This victory enabled Lolich to outduel Gibby in the seventh and deciding game.

The Tigers wound up winning their first World Series title in 23 years, a year after the race riots that tore Detroit apart. For that one summer, a baseball team brought Motown together.

American League All-Star

A three-time All-Star, Denny McLain reprised his Cy Young win the following year, when the pitcher’s mound was lowered from 15 inches to 10 and the strike zone was reduced in the interest of maintaining competitive balance between pitchers and hitters. (This was a concept that was unceremoniously ash-canned by Baseball Commissioner Bud Selig after the 1994–95 strike, when — desperate to get fans back — juiced balls and juiced hitters became the norm, triggering an offensive explosion not seen since the introduction of a lively ball into the National League in 1930, an experiment that lasted one year.)

A 20 game-winner in 1966 (a late season foot injury in ’67 limited him to 17 victories), McLain followed up his 31 victory season with a league-leading 24 wins in 1969. He was sitting in the catbird’s seat among American League pitchers at the end of the 1960s, yet Denny is not in the Hall of Fame, nor will he ever be, unlike his father-in-law, Lou Boudreau.

McLain entered The Show for a “cup of coffee” at the end of the 1963 season, when he was 19 years old. Despite an early start and tremendous talent, McLain only played in the Big Leagues for 10 years.

Other pitchers with abbreviated careers are in the Hall of Fame, such as Dizzy Dean and Sandy Koufax, but their careers were shortened by injuries: McLain’s career was shortened by gambling. In fact, some believe that McLain’s gambling addiction might have cost the 1967 Detroit Tigers the American League crown, in one of the most exciting pennant races ever. There are stories that McLain’s foo was broken by mobsters, taking him out of the lineup at a crucial time for the Tigers’ chance of winning the League title.

In 1968, McClain went 24–9 with a 2.80 ERA. For his second superlative season, Denny McLain won his second Cy Young Award, ending up tied after the baseball writers’ vote with the Baltimore Orioles’ 23 game-winner, Mike Cuellar. However, McLain’s happiness was destined to be short-lived, as as with career, as Sports Illustrated soon revealed that McLain, a degenerate gambler, was covering his gambling losses by running a bookmaking operation and associated not only with fellow gamblers but with Mafia figures.

The Wages of Sin

The Sports Illustrated article (published in February 1970) claimed that the foot injury suffered by McLain late in the 1967 season that limited his appearances during the critical end-of-season pennant race was the result of a mafiaso stomping on it due to the pitcher having failed to pay off a gambling bet. McLain’s bookmaking operation, which operated out of a restaurant in Flint, Michigan, had failed to cover a $43,000 loss by one of its subordinate bookies. When McLain refused to pay off after several months, the disgruntled gambler contacted mafia soldier Tony Giacolone, who threatened McLain, then broke his foot.

The foot injury, the cause of which McLain never satisfactorily explained, led to his missing six starts during the climax of the 1967 season, when the Tigers were in contention with three other teams, including the Boston Red Sox and the Minnesota Twins (the 1965 American League champions) for the A.L. pennant. The race went down to the final day, and when McLain was called on to pitch the final game of the season for Detroit, he lost, which meant that the Red Sox, managed by rookie field boss Dick Williams (a future Hall of Famer), won the pennant. The 1867 Red Sox victory was dubbed “The Impossible Dream” pennant.

Tony Giacolone, according to the Sports Illustrated story, had bet on the Red Sox and the Twins to win the pennant. He also put a bet on the Angels to win the last game of the season, a game that was lost by McLain.

McLain denied most of the details in the story. He told Baseball Commissioner Bowie Kuhn that he had invested $15,000 in a bookmaking operation, but was no longer involved with it at the time of the ’67 pennant race. However, McLain also admitted to loaning one of his “former” partners in the bookmaking operation $10,000 to pay off the gambling debt that Sports Illustrated had linked to his broken foot, but he claimed to have never met Giacolone.

The revelations lead Kuhn to suspend McLain for the first three months of the 1970 season. After an investigation conducted by the newly constituted Major League Baseball Office of Investigations, Kuhn exonerated McLain for his involvement in bookmaking, claiming that he had been duped. Most sportswriters considered the Kuhn investigation a whitewash.


Denny McLain’s performance on and off the field that during the last half of the 1970 season was erratic, and the Tigers suspended him for throwing water on two sportswriters. This was followed by his second suspension by Commissioner Kuhn, for carrying a gun on a team flight. This second suspension cost McLain the rest of the season, during which the reigning Cy Young champ went 3–5 with a 4.63 E.R.A.

Deprived of most of his income from baseball, McLain declared bankruptcy, claiming debts of $446,069 (approximately $3 million in 2020 dollars, when factored for inflation) against assets of $413. The troubled McLain never recovered his sense of equilibrium. Traded to the Washington Senators (“Washington: First in war, first in peace, and last in the American League”) the following season, the three-time 20-game winner lost 20 games, going 10–22 with a 4.28 E.R.A.

McLain’s 22 losses lead both leagues. The closest to another 20-game loser was Steve Arlin of the San Diego Padres in their sophomore year, who lost 19.

The former MVP was traded to the A.L. East Champion Oakland A’s for former 1967 National League M.V.P.(and future Hall of Famer) Orlando Cepeda, who had faced McLain in the ’68 World Series. Already in possession of his own MVP & Cy Young Award-winning pitcher Vida Blue, no-nonsense ex-Marine manager Dick Williams ( whose ticket to the Hall of Fame was piloting three different teams that won four pennants and two World Series) was unimpressed.

Williams cut McLain from his team that would go on to win the first of its three straight World Series Championships that October, after his first five starts produced only one victory against two losses and a 6.04 E.R.A. (This was an era when an E.R.A. over 4.00 could doom a starting pitcher.) McLain ended his major league career later that season in the National League East on the Atlanta Braves, where as a spot starter and reliever, he went 3–5 with an egregious 6.50 E.R.A.

Denny McLain was through at the age of 28. His troubles were not.


Denny McLain attempted a comeback in 1973, by pitching in the minor leagues. He also pitched in the minors in 1974, but his performance was hampered by arm troubles. After abandoning his attempts at a comeback, McLain continued to associate with gamblers and organized crime figures, including Anthony “The Ant” Spilotro, a notorious enforcer for the Chicago “Outfit”, as organized the Mob is known in the Windy City. A talented golf player, McLain hustled marks for cash. As a licensed pilot, he reportedly once flew a felon out of the country for a fee reported variously as $100,000 and $160,000.

Eventually, Deny McLain’s association with gamblers and the Mob caught up with him. In March 1984, the U.S. Justice Department indicted McLain under the federal Racketeer Influenced and Corrupt Organizations Act (RICO) statute for racketeering, extortion, and trafficking in cocaine. Convicted, McLain received 23 years in prison, though he was released less than three years later on a technicality. The federal government dropped the case.

After being released from prison, McLain seemed to get his life in order. He made the rounds of card-signing shows and got a gig as a radio-announcer. However, McLain seemingly had a taste for criminality. Some observers speculated that it was rooted in the star athlete’s feeling of omnipotence, that they could do no wrong.

Along with a partner, McLain bought a financially troubled meat-packing company In 1993. Soon after the sale, it was found out that $2.5 million in Peet Packing’s pension funds were missing, and the firm went bankrupt in 1995. McLain and his partner were convicted for embezzlement, money laundering, mail fraud, and conspiracy, and Denny McLain was once again sentenced to jail: In 1996, he received an eight-year sentence.

Even then, his legal woes persisted. In 1998, McLain was indicted along with John Gotti, Jr. on charges of running a phony telephone calling card ring, though the charges eventually were dropped.

Denny McLain served six years of his eight-year prison term. After his release, he tried to get his life back in order, remarrying his wife (who had divorced him after his second stint in stir), and writing his autobiography, I Told You I Wasn’t Perfect, which was published in 2007. But the legal woes continued. McLain found himself in legal hot water in April 2008, when he was arrested for failing to appear in court in a civil matter.

At that time, Denny McLain owed creditors over $60,000. One creditor, a Texas-based law firm that represented McLain and his telecommunications company, CloudVoice Telecom, has been hounding him for $17,500 in fees. (CloudVoice Telecom was based at McLain’s home in the Detroit suburbs and listed him as its president.) The law firm has attempted to collect on its debt since late 2007, but claimed that McLain, who still generated income at card shows, funneled the card show funds through an out-of-state agent. For failing to appear at a court hearing into the matter, McLain was arrested by the sheriff, who had gone to his home to seize property to satisfy his outstanding debts.

When he was arraigned and bail was set on the charge, McLain told the court he was broke, though he later managed to raise the amount needed to spring himself from jail. The sheriff has seized property and sports memorabilia and plans to auction off McLain’s possessions to satisfy the judgments against him. The IRS put a lien on his baseball pension to help pay restitution to his victims.

Good Standing

Unlike Pete Rose, who was banned from life from the game, Denny McLain remains in “good standing” with major league baseball, despite his troubles, past and present. In fact, he was back on the field at Detroit’s Comerica Park on the night of June 26, 2008, when the Tigers organization honored the World Series winners of 40 summers ago. He signed autographs for fans at one of the desks set up for the 1968 Tigers teammates who made it back for the festivities.

Writing in the Detroit Free Press , freelance writer Ryan Schreiber said that the fan reaction to McLain was mostly positive.

“Because of his off-field problems, including two stints in the federal prison system,” Schreiber wrote, “McLain has been an enemy of many in the Detroit area, but he received mostly cheers when announced before Tuesday’s game. Why? Have fans forgiven and forgotten, or do they just look the other way when is comes to talented athletes?”

Writing in the same paper, Drew Sharp reported, “A mixture of applause and jeers greeted McLain’s introduction Tuesday at Comerica Park with other members of the 1968 World Series champions.”

Sharp believes that the Tigers should officially recognize Denny McLain’s achievement, despite his personal odiousness, as winning 30 games is a sports feat that will never be matched again.

It is true that the feat never will be accomplished again. Unlike Barry Bonds’ home run record, or even Joe DiMaggio’s hitting streak, the game of baseball has changed significantly in ways that ensure a pitcher never gets a crack at 30 wins again. Trends in baseball during the last generation have favored hitters, but it is not just an issue of those things that have eroded the competitive balance between pitchers and hitters, like the under-reported story of the proliferation of baseballs with off-centered pills being used in the Big Leagues.

A healthy hitter can go out and play in 162 games a year if he wants to. By contrast, a #1 starter will get, at most, 33–34 starts a year. Since the 2010 season, when Chris Carpenter racked up 35 starts one year after Justin Verlander did the same thing, the past nine full seasons have produced only two pitchers who started 35 games: Boston’s David Price in 2016 and Milwaukee’s Jhoulys Chacín in 2018.

Price won 17 games, and Chacin notched won 15, less than half the total number of victories scored by Denny McLain in 1969.

In McLain’s time, a #1 starter got 40 starts, and the #1 starter 41, or more if needed, being brought in on short-rest during a tight pennant race. Today’s top pitchers go to the mound every fifth day and are expected to last only six innings. In Denny McLain’s era, starting pitchers went to the hill every fourth day, and were expected to last as long as they could. In 1968 & ’69, McLain averaged over 8 innings a start, racking up 661 innings in 83 games, all but one of them starts.

Yes, Denny McLain’s 30+ victories was a feat likely never to be repeated. There has been only one 30 game-winner in the past three-quarters of a century. But as for the Tigers or Major League Baseball honoring him for his achievement, I wouldn’t bet on it.