Retired Major League Baseball star and convicted felon Denny McLain’s reputed ties to the New York mafia are explored in a new book penned by former U.S. Secret Service agent Nino Perrotta, who investigated a phone-card scam allegedly perpetrated in tandem between McLain and New York’s infamous Gambino crime family in the late 1990s. Perrotta’s book is called Dual Mission. Charged alongside several top Gambino syndicate leaders in a 1998 federal racketeering indictment, the case against McLain, 72, was eventually dropped.

Deadline Detroit ran an excerpt from Dual Mission this week on its website. You can see the article and read the excerpt here.

A two-time CY Young Award winner and the last MLB hurler to post a 30-win season, McLain has been dogged by rumors of intermingling with the mob since his professional pitching prime in the late 1960s. McLain went 31-6 in 1968, leading his Detroit Tigers to a World Series championship, claiming an American League MVP award and his first of two straight Cy Youngs.

The year before, the Tigers’ ace missed two starts deep in the 1967 pennant race which they wound up narrowly losing to the Boston Red Sox due to a toe injury law enforcement sources attribute to a physical altercation with Detroit mob captain Vito (Billy Jack) Giacalone and related to a hefty unpaid debt belonging to the Chicago born-and-bred McLain. Giacalone and his older brother Anthony (Tony Jack) Giacalone controlled all the illegal gambling in the area and were suspects in multiple gangland slayings.

According to underworld lore and statements made by federal informants, McLain racked up close to $50,000 in debts tied to betting on horse racing and encountered an ornery Billy Giacalone at a Labor Day weekend party held on a yacht docked on the Detroit River where Giacalone intentionally stomped on his foot. Giacalone was far from star struck upon seeing his celebrity debtor at the gathering.

“I don’t know how they do things in Chicago, fat boy, but in this town you pay what you owe no matter who you are,” he is alleged to have told the husky-built McLain prior to obliterating his toe with the heel of his boot.

In 1970, McLain served three separate suspensions issued by MLB, one for running an illegal gambling operation himself, one for dousing a pair of sports writers with a bucket of water and still another for bringing a gun on the Tigers’ team airplane. MLB investigators found McLain had booked bets for a local mob-backed gambling outfit overseen by Don (Donnie Dice) Dawson, a highly-placed associate of the mafia in Detroit and one of the most prolific bookmakers in the country throughout the 1950s and 1960s.

Dawson admitted to paying players on the Detroit Lions to fix pro football games. Lions Hall of Fame defensive lineman Alex Karras was suspended by the NFL for the entire 1963 season for his gambling affairs, ownership stake in a mob-connected bar and grill in downtown Detroit and links to Dawson, the Giacalone brothers and other Motor City mobsters as well. Tony Jack died in 2001 of natural causes, his baby bro Billy Jack followed more than a decade later in 2012.

FBI surveillance logs from the 1970s show McLain dining and socializing with Chicago mob enforcer Anthony (Tony the Ant) Spilotro in Las Vegas. McLain spent a great deal of time in Las Vegas, even holding gigs at hotels on the Strip playing the organ. The small, but ferocious Spilotro was the Chicago mob’s point man in Vegas and on the west coast and died viciously, beaten, stomped and strangled to death in June 1986 for gross insubordination in a gruesome killing depicted in the movie Casino.

McLain pitched his last game in the pros in 1972 for the Atlanta Braves. Retirement wasn’t kind to him. Twice he was imprisoned, first in 1985 for racketeering and narcotics conspiracy charges out of Tampa, Florida and then in the 1990s for stealing three million bucks in pensions from workers at a meat-packing plant he owned in Chesaning, Michigan. The racketeering and drug bust was overturned on appeal and he pled guilty to lesser charges in 1988.

McLain’s co-defendant in the racketeering and drug case was New Jersey organized crime figure Frank Cocchiaro. Court records named Cocchiaro a protégé to slain Monmouth County mob boss Anthony (Little Pusso) Russo of the Genovese crime family.

While McLain was serving time in prison for his pension fraud case, he got himself indicted with 40 members and associates of the Gambino mob out of New York stemming from his ownership of a telecommunications company in Michigan. The indictment alleged McLain was teaming with the east coast wiseguys – and in some cases even ripping them off – in a series of phone-card scams aimed at duping foreigners. Federal wiretaps intercepted chatter between several different sets of Gambinos mentioning McLain and his company by name in their conversations about the alleged scams.

McLain’s son-in-law told investigators he and McLain traveled to New York on a number of occasions to meet with Gambino mob soldier Anthony (Tony the Carpenter) Plomitallo and discuss details of the racket. Plomitallo was a driver, bodyguard and emissary for then-Gambino boss John Gotti, Jr., who pled guilty in the case much to the chagrin of his incarcerated father, John (The Dapper Don) Gotti, the iconic, image-obsessed 1980s and early 1990s Big Apple Godfather. “Old school” Gambino capo Greg DePalma was also nailed in the case.

The elder Gotti succumbed to cancer behind bars in 2002. Today, Gotti, Jr. is said to be retired from the mafia. McLain has repeatedly denied ever knowing Gotti Jr. and currently lives back in suburban Detroit.

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