Ex-bookie gets 2 years in prison in case tied to Chicago mob probe

A Wood Dale man was sentenced to two years in prison Friday for running an illicit sports gambling ring uncovered as part of a larger federal investigation into the Chicago Outfit.

Michael Frontier, 39, a former mixed-martial arts fighter who currently works for a national cannabis firm, pleaded guilty in January to one count of running an illegal gambling business.

In a plea agreement with prosecutors, Frontier admitted that in 2015 and 2016, he ran a team of at least five agents, recruiting gamblers and placing wagers on games through an online company based in Costa Rica. To avoid detection, Frontier paid an underling to use MoneyGram to wire cash to Costa Rica under aliases such as “Ira Goldberg” and “Brian Seagal,” according to his plea deal.

Frontier admitted in the plea that he hid his substantial income as a bookie in bankruptcy proceedings in an effort to avoid paying a $1.5 million civil judgment filed against him as part of a lawsuit over a motorcycle accident in DuPage County.

In September 2015, Frontier testified under oath in the bankruptcy case that his occupation was “mainly painting, but also carpentry” and that he made only $7,500 in gross earnings that year, according to the plea agreement.

Before the sentence was handed down Friday, Frontier stood in court and apologized to U.S. District Judge John Robert Blakey for his actions, saying he’s turned his life around since voluntarily quitting the gambling business in 2016, before he even knew he was under investigation.

“I’m a whole different person from that time until now,” said Frontier, dressed in all black and sporting tattoos on top of his shaved head. “I’ve changed my life and I’m just hoping I get a second chance.”

While Frontier was not accused of being in the mob himself, he was captured on federal wiretaps in 2016 and 2017 as the FBI was attempting to build racketeering cases involving the Outfit’s notorious Elmwood Park and Grand Avenue street crews, court records show. The investigation was focused on two of the Outfit’s bread-and-butter rackets: Prostitution and gambling, according to the court records.

Among those under investigation were a close relative of Outfit loan shark Joseph “Joe Gags” Gagliano, a twice-convicted mob bookmaker reputed to be a “capo” in the Elmwood Park crew, and gambling chief Marco “The Mover” D’Amico, the onetime second-in-command in Elmwood Park who died in 2020 at age 84, the records show.

Frontier was captured on the wiretaps talking and meeting with Gagliano’s relative, as well as with Gene “Gino” Cassano, a mob-connected west suburban businessman and bookie who was later charged with extortion related to a customer’s beating over an unpaid “juice” loan, according to court records.

Recordings made in the case captured one episode where Frontier threatened a gambler who was having trouble paying back a $25,000 loan Assistant U.S. Attorney Amarjeet Bhachu revealed in court Friday.

“I swear on my mother, if I don’t get my money, I’ll kick your ass,” Frontier told him, according to Bhachu.

In another recording about the debtor, Frontier told an associate, “He’s getting beat up no matter what now,” Bhachu said.

Bhachu said that while no beating ever occurred, the conversations showed Frontier “at one point in time” was operating his business “through the use of threats and violence.”

Another bettor told investigators that when he did not have the money to pay his gambling debt, “Frontier put him in contact with someone from whom he could borrow money,” according to a court ruling from Blakey last year.

When that bettor showed up to meet the person, he was “blindsided and beaten” by several men who told him to pay up or else, according to an FBI affidavit quoted in Blakey’s ruling.

In arguing last year for a hearing on whether the FBI misled the judge who approved the wiretaps, Frontier’s attorney, Francis Lipuma, said investigators unfairly lumped Frontier in with real mobsters and relied on informants with sordid pasts who often gave conflicting accounts.

“If you look at the mob figures that they talk about, all the way back to Joey Lombardo and James Marcello and the murder of the Spilotro brothers, there’s pages and pages of their criminal history in there but they don’t give the same treatment to their informants,” Lipuma said, according to a transcript of the July 1, 2023, hearing.

In arguing Friday for a sentence of one year in prison, Lipuma said Frontier’s bookmaking lasted only for a short period and never grew to a scale typically seen in federal prosecutions. He also noted that Frontier was abusing alcohol at the time following the tragic death of his brother, and later “made an independent decision on his own” to shut down his gambling business and stop hanging out with people who led him astray.

“He expelled all the negative influences in his life,” Lipuma said, without naming anyone specific. “He has had no association with them in years.”

In the eight years since ending his bookmaking, Frontier has made a name for himself at Verano, a leading cannabis company where he helped the business nationally and has recently transitioned into a role helping develop new products, according to Lipuma’s recent sentencing filing.

He’s also expecting his first child with his girlfriend in June, Lipuma wrote.

“Nowadays, you can find him in one of three places: at work, at the gym, or at home,” Lipuma wrote.

Frontier was among a handful of defendants charged as part of the wider Outfit probe, though none of the reputed bosses who were under investigation have been indicted.

Also charged was Jessica Nesbitt, a Chicago madam who was running a fetish and prostitution business out of her Near West Side condo building and was suspected of paying protection money to Gagliano’s relative. Nesbitt pleaded guilty and was sentenced last year to home confinement and probation.

Cassano, meanwhile, was charged along with an associate, Gioacchino “Jack” Galione, with extortion related to a “juice” loan beating in Addison. All charges against them were dismissed last month after their trial ended in a mistrial.