How Cleveland Mafioso Allie Calabrese Died In ’99 Might Have Gone To The Grave With Joe Loose

April 20, 2020 — The mystery surrounding the 1999 death of Cleveland mobster Alfred (Allie Con) Calabrese is an intriguing part of Joseph (Joe Loose) Iacobacci’s legacy as mafia don of Ohio. Iacobacci, 70, died of natural causes in retirement last Thursday. He headed the Cleveland mafia from the early 1990s until he voluntarily walked away from the underworld and his role as boss at the end of 2005, per FBI records.

Joe Loose and Calabrese were longtime close friends. They were both known for their tenacity as gangsters. As a tandem, they brought the crime family in Cleveland back from the brink of extinction three decades ago and then went down together in a multi-million dollar bank scam, which reportedly fractured their tight relationship and led to lingering bad feelings.

It might have also led to Calabrese’s murder behind bars. Or maybe it wasn’t a murder at all.

In the 1970s, Iacobacci and Calabrese were part of a prolific burglary and mob enforcement crew operating out of the Collinwood neighborhood on Cleveland’s southeast side. Iacobacci, mustachioed and built like a bull with a barrel chest and meat-clever hands, was a bodyguard for Cleveland mafia don James (Jack White) Licavoli. Calabrese, smaller, slimmer and darker-skinned, ran gambling and loansharking rackets for capo Tommy (The Chinaman) Sinito. Along with Sinito, they were suspects in a spate of murder conspiracy investigations during Licavoli’s reign tied to a war against the city’s Irish mob that raged for a chunk of the “Me” decade.

By the late 1980s, Joe Loose and Calabrese were both in federal prison for narcotics trafficking, serving their time together in a correctional facility in Milan, Michigan, near the Ohio border. Calabrese got nailed for selling five kilos of cocaine to an undercover FBI agent in 1984. Iacobacci was busted in a separate cocaine-trafficking conspiracy case three years later.

While in Milan, Joe Loose, Calabrese and Calabrese’s pal Paul Weisenbach, a white-collar criminal with a talent for stock rip-offs and the flimflam game, began planning a restructuring of the Cleveland mob for when they got out, per court documents. Weisenbach was locked up for defrauding the Society National Bank by putting up phony stock options as collateral for three loans totaling almost a quarter million bucks. He had grown up in Collinwood, but moved to New York, got his stockbroker’s license and went on to fleece Wall Street for years before getting jammed up in the Society National Bank securities fraud case.

Using Weisenbach’s huckster skill-set as a base, Iacobacci and Calabrese decided to focus their regime around boardroom racketeering and non-violent con artistry, more than traditional street crimes and gangland thuggery of their youth. When they were all finally on the outside together in the early 1990s, Iacobacci officially took power in the Cleveland mafia and named Calabrese his underboss. Weisenbach was their unofficial “finance consigliere.”

Jack White had died of a heart attack in a Wisconsin federal prison in 1985. Tommy Sinito dropped dead of a bad ticker in the yard at an Ohio correctional facility in 1997. The mob in Cleveland was Iacobacci’s and Calabrese’s to do with what they pleased.

They followed Weisenbach down a road filled with stacks of money and a return to gangland prominence that eventually winded into a forest of peril, sending them both back to the clink and severing their friendship forever. The cash proved too blinding.

Doing an interview with Cleveland Scene magazine in 2004, Weisenbach laid out the bank scam the buried the Ohio mafia.

Weisenbach introduced Joe Loose and Calabrese to a scam he called the “California Swing,” where they opened east coast bank accounts and deposited millions of dollars of bad checks with California routing numbers that couldn’t be voided for ten days. During the lag time, Weisenbach would move the money to offshore accounts and then to Swiss accounts days and finally back to the U.S. through Chicago banks before the financial institutions in New Jersey knew what was going on.

Iacobacci and Calabrese brought mobsters from Chi-Town and Jersey in on the California Swing score and things were flush once again in the Cleveland mafia. Over a period of less than two years, they stole upwards of $5,000,000. The good times were short-lived though.

Calabrese had to attend a sit down in Newark, New Jersey with Lucchese crime family capo Mike (Mad Dog) Taccetta in January 1992 in to settle a beef with the Jersey wing of the California Swing score over past Weisenbach indiscretions related to the Taccetta crew. Taccetta and his relatives run the Lucchese’s Jersey rackets.

As part of the deal made at the sitdown, Taccetta was supposed to receive an extra cut of the California Swing to make up for the some $200,000 Weisenbach had stolen from a Jersey mob button back in the 1980s. Iacobacci felt the money should come out of Weisenbach’s cut, but Weisenbach thought Joe Loose should foot the bill because the whole score was Weisenbach’s brainchild. Tension between the pair began to rise with Calabrese playing mediator.

In July 1992, the FBI pinched Weisenbach for a parole violation and convinced him to cooperate and help agents break up the California Swing scam. Weisenbach claims the feds played a wiretapped conversation of Iacobacci discussing killing him. Per court filings, he taped 200 meetings with associates. He admitted to allowing the FBI to bug his car and avoided indictment in the case.

Weisenbach’s cooperation drew the ire of Joe Loose. Calabrese had to run interference on Weisenbach’s behalf again and the issue drove a wedge between the two wiseguys and Cleveland mob leaders.

On November 20, 1994, Weisenbach was shot in the wrist in an attack outside a bar in The Flats, Cleveland’s main nightlife district at the time, that killed his friend, 26-year old Mike Roman. Weisenbach thinks it was a mob hit gone wrong aimed at taking him out that felled Roman instead.

After a night of drinking at the Flat Iron Inn, Roman and Weisenbach headed for the parking lot when they were approached by a local drug dealer named Sam Bulgin, who Roman had verbally sparred minutes earlier and then took a swing at him. Bulgin took out a .38 revolver and took aim and pumped three bullets into Roman’s chest. He turned to Weisenbach, but Weisenbach grabbed the gun as it went off and was able to flee with just a surface wound.

In the months before Sam Bulgin was found guilty at 1998 trial for the Roman murder, his brother Pete was found shot to death inside his apartment on Cleveland’s eastside. Sam Bulgin denies that he was the triggerman in the slaying. Weisenbach told Cleveland Scene that the Pete Bulgin hit was punishment for Sam botching the first job.

Joe Loose and Allie Calabrese were indicted in 1995 in the California Swing scam. Weisenbach wasn’t arrested in the case, deemed an unindicted co-conspirator. Iacobacci pleaded guilty and served two years in prison. He walked free in April 1998. Calabrese had more time to do because his arrest in the California Swing case violated his parole from his coke conviction.

This is where things get even more hazy. On August 10, 1999, Calabrese died in prison at 56 under a shroud of speculation, whispers and innuendo. Some say he was beat to death with a pipe on a murder contract placed on his head from the outside via Joe Loose. Some say, he suffered a stroke. Others, that he died after accidentally slipping and hitting his head on a sink.

No charges were ever brought in Calabrese’s death. The Cleveland mob in 2020 is a modest band of old-school bookies, gamblers, thieves and minor drug pushers.

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