John Matassa, Longtime Union Boss and Reputed Mob Figure Pleads Guilty to Embezzlement

A reputed Chicago mob figure and longtime union boss pleaded guilty Tuesday to a federal felony charge of embezzlement in an alleged scheme to fraudulently qualify for early retirement benefits.

John Matassa Jr., 67, known by the nickname “Pudgy,” faces up to about 21 months in prison after entering his plea on the lone count before U.S. District Judge Matthew Kennelly, according to a plea agreement with prosecutors.

"The guy's hanging on to the carpet like a cat," one union member told the Tribune at the time. "He's just not cooperating at all. I just can't wait until he's gone."

Matassa’s name also surfaced during the 2009 trial of a deputy U.S. marshal who was convicted of leaking sensitive information to a family friend with alleged mob ties, knowing the details would end up in the Outfit's hands. Matassa allegedly acted as a go-between.

The leak involved the then-secret cooperation of Outfit turncoat Nicholas Calabrese, whose testimony led to the convictions of numerous mob figures — including Marcello — in the landmark Operation Family Secrets investigation.

Calabrese testified at the Family Secrets trial that Matassa was present in October 1983 when Calabrese was indoctrinated as a “made” member of the mob at a ceremony at a shuttered restaurant on Mannheim Road.

Matassa, the former secretary-treasurer of the Independent Union of Amalgamated Workers Local 711, was charged in a 10-count indictment in 2017 with putting his wife on the union’s payroll in a do-nothing job while lowering his own salary.

He then applied for early retirement benefits from the Social Security Administration's Old-Age Insurance program, listing his reduced salary to qualify for those benefits, the indictment alleged.

The charges also alleged that Matassa personally signed his wife's paychecks from the union over a four-year period and had them deposited into the couple's bank account.

According to Matassa’s 18-page plea agreement, preliminary sentencing calculations call for him to be given 15 to 21 months in prison, but Kennelly will make the final decision. Matassa must also pay a total of $66,500 in restitution to the union and Social Security Administration, according to the agreement.

Kennelly set sentencing for May 22.

Dressed in a purple checkered shirt, the husky Matassa, of Arlington Heights, leaned against a lectern and answered, “Yes, your honor” in a deep voice as Kennelly asked him if he understood the terms of his plea deal. About halfway thought the 40-minute hearing, Matassa accepted the judge’s offer and took a seat.

For years, Matassa has been associated with some of the Outfit’s most notorious figures, including former reputed boss James “Jimmy Light” Marcello.

In the late 1990s, Matassa was kicked out as president of the Laborers Union Chicago local over his alleged extensive ties to organized crime — a move Matassa fought for years.

"The guy's hanging on to the carpet like a cat," one union member told the Tribune at the time. "He's just not cooperating at all. I just can't wait until he's gone."

Matassa’s name also surfaced during the 2009 trial of a deputy U.S. marshal who was convicted of leaking sensitive information to a family friend with alleged mob ties, knowing the details would end up in the Outfit's hands. Matassa allegedly acted as a go-between.

The leak involved the then-secret cooperation of Outfit turncoat Nicholas Calabrese, whose testimony led to the convictions of numerous mob figures — including Marcello — in the landmark Operation Family Secrets investigation.

Calabrese testified at the Family Secrets trial that Matassa was present in October 1983 when Calabrese was indoctrinated as a “made” member of the mob at a ceremony at a shuttered restaurant on Mannheim Road.

Thanks to Jason Meisner.