Chicago Outfit-tied scammer Lee Anglin promised to make good to his victims. Now, he’s going back to prison.

After doing 12 years for stealing $10 million in a Ponzi scheme, he said he was a changed man. But a judge is sending him back to prison over his latest ventures.

SHARE Chicago Outfit-tied scammer Lee Anglin promised to make good to his victims. Now, he’s going back to prison.
Lee Anglin in 2018.

Lee Anglin in 2018.

Maria de la Guardia / Sun-Times file

After Lee Anglin walked out of prison nearly three years ago, he said he was a changed man, no longer interested in the temptations offered by his former Chicago underworld associates.

He even vowed to repay the people from whom he’d stolen more than $10 million in a real-estate Ponzi scheme.

Now, he’s headed back to prison.

Federal prosecutors say Anglin, 50, came up with new money-making schemes and violated the terms of his probation, which a federal judge in Chicago has revoked. U.S. District Judge Robert Gettleman has ordered Anglin to report by June 29 to begin serving six more months in prison.

Anglin — whose colorful past includes stints as a debt collector for loansharks and as the owner of a restaurant and bar in business with the Chicago Outfit — failed to provide his probation officer with details of his latest business dealings, which she needed to know about so she could monitor the “risk to others,” according to the judge’s order.

Those ventures included providing legal services for inmates, even though he isn’t a lawyer, and negotiating to buy two businesses in Utah.

Gettleman wrote that Anglin — who once boasted of having been a jailhouse legal adviser to his fellow inmates — also failed to get his permission for “any employment providing legal services, consultation or representation without the permission of the court.”

Anglin, who couldn’t be reached, denied he violated the terms of his probation, according to the judge’s order.

In a series of interviews for a Chicago Sun-Times story in July 2018, Anglin spoke about his shady past. He said then that he’d run a bookmaking operation at a bar in Melrose Park, splitting the take with James “Little Jimmy” Marcello, a mob underboss authorities said controlled the west suburbs for the Chicago Outfit and went to prison for life after being convicted in the landmark Operation Family Secrets trial.

Anglin said he also was once in business with Outfit figures in restaurants and bars and partnered in one venture with the sister of the late reputed mob hit man Anthony “Tough Tony” Calabrese.

He said then, “I led a normal businessman’s life in the corporate world by day and a criminal lifestyle at night.”

He spoke of his plans to repay the millions prosecutors say he scammed from investors and said, “I’m a different person now.”

“I don’t want to be having backroom meetings and exchanging envelopes and dealing with, you know, illegal gambling and all those things,” he said then. “I’m done with all that.”

He’d served 12 years of a 15-year sentence for running a sham real-estate scheme between 2004 and 2006 in which his early investors got paid off with money put in by later investors who were left with nothing, though he’d run ads in The Wall Street Journal promising a “guaranteed return.”

After he was freed in 2018, Anglin was required to live in Chicago to serve out his probation. His wife Jenni stayed in Utah where she’d been living while was in prison.

Lee Anglin in 2000 at the office of a newspaper he ran.

Lee Anglin in 2000 at the office of a newspaper he ran.

Sun-Times file

Anglin and his wife operated an investment company after he got out of prison, according to prosecutors, who told the judge that, in 2019, Anglin negotiated on behalf of the investment company to buy a heavy-equipment rental business in Utah. The deal wasn’t completed but Anglin didn’t tell his probation officer about it, as required.

Last year, Anglin negotiated to buy All Torqued Up — an oilfield-servicing business in Utah — from a couple “experiencing personal difficulties” including their child’s treatment for leukemia.

But the Anglins’ company failed to pay off the company debts, a requirement for the deal to go through, prosecutors say. That put the couple who owned All Torqued Up at “further financial risk,” according to Anglin’s probation officer, who said in a court filing she wasn’t told in advance about either deal.

Prosecutors say that, while on probation, Lee Anglin also was paid to prepare legal documents for inmates through Nationwide Legal Assistance Group, a company he and his wife created, and that he didn’t get the judge’s permission, as required.

After Gettleman was told about Anglin’s legal work, the judge asked Anglin’s criminal defense lawyer to finish handling it.

Brian Whitfield, who’s doing 12 years for tax fraud, wrote to Gettleman to complain about Anglin’s legal work on his case. Whitfield, who owned a Tennessee employee-outsourcing company, said in his letter to the judge that Anglin submitted a “shoddy” post-conviction petition on his behalf without letting him see it first.

“Lee and Jenni Anglin are unscrupulous people,” Whitfield told the judge, according to court records. “At a minimum, they grossly misrepresented their competencies, concealed Anglin’s issues with this court and scammed Whitfield out of more than $24,000 in the process.”


Click here to read the Sun-Times’ July 29, 2018, report on Lee Anglin.

Click here to read the Sun-Times’ July 29, 2018, report.

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