Lee Anglin is back in town.
He might not be a household name, but he certainly is well known in Chicago’s underworld.
His colorful resume includes stints as: a debt collector for loansharks, a politically connected newspaper publisher, a restaurant and bar owner in business with the Chicago Outfit, a crooked real-estate investor and scam artist and a legal adviser to his fellow prison inmates.
Anglin was released in May after more than 12 years behind bars for stealing millions of dollars from investors in a real-estate scheme.
After getting out, the 47-year-old South Sider’s plan was to move to Utah. He says he wants to get far away from the temptations of Chicago and his former criminal associates.
“I am no longer interested in strip clubs and party nights,” Anglin says.
He got approval from a federal judge to go to Utah, his fiancée’s home state. But then he found out he’d have to stay in prison for several more months before the federal Bureau of Prisons could process his paperwork.
So he decided to come home. He began his three years of probation with a stay at a Salvation Army halfway house in Chicago. Earlier this month, he moved to the south suburbs. He’s living with his fiancée in a modest brick house in Lansing for now.
In a series of interviews with the Chicago Sun-Times, Anglin spoke about growing up on the South Side and how he connected with legendary Chicago figures such as former Ald. Edward “Fast Eddie” Vrdolyak (10th) and mob boss James “Little Jimmie” Marcello. He talked about life in prison and his intention to repay the millions of dollars prosecutors say he pilfered from investors.
And he described how, for him, the worlds of commerce and crime in Chicago intersected.
“I led a normal businessman’s life in the corporate world by day and a criminal lifestyle at night,” says Anglin.
Anglin, who’s Italian-American, grew up on the Southeast Side, in Hegewisch. He says he learned to box and, as a teenager, began collecting gambling debts for loansharks.
Vrdolyak, who was the most powerful politician in the neighborhood, was his idol.
“I was always grabbing buddies of mine and, in the middle of the night, tearing down political signs from opposing candidates,” Anglin says.
He says he saved enough from various hustles to be able to buy an Italian restaurant when he was just 18.
A few years later, when the Hegewisch News went bankrupt, Anglin says that, with Vrdolyak’s encouragement, he bought the weekly newspaper in 1990 and used the publication to support Vrdolyak and other 10th Ward politicians.
“I was losing money on the paper because it was so biased,” Anglin says, and he laughs. “But that was made up with illegal earnings from bookmaking and loansharking.”
Vrdolyak, a part-owner of the News, wrote a law column for the paper. He’s now facing federal charges that accuse him of obstructing an IRS investigation.
Anglin says he opened another newspaper, the Midway Times, in 1993 in partnership with then-Ald. James Laski, who later served as Chicago’s city clerk before going to prison for corruption in the scandal that engulfed the city’s Hired Truck Program.
The purpose of the Midway Times was to oppose then-U.S. Rep. Bill Lipinski, D-Chicago, according to Anglin, who at the time was in his early 20s. He says Lipinski pressured him to close it.
The following year, 1994, Anglin declared personal bankruptcy. Later, he ran a weekly newspaper chain in the south suburbs and northwest Indiana called the Journal News Group, which went bust in 2002.
While he was running newspapers and writing outrageous columns, Anglin says he also was rehabbing houses and buying restaurants, bars and other businesses, some of his enterprises in partnership with the Outfit.
He says he ran a bookmaking operation at a bar in Melrose Park and split the proceeds with Marcello, a mob underboss authorities have said controlled the west suburbs, who’s now doing life in prison after being convicted in the landmark Operation Family Secrets mob trial. He says he also partnered in a restaurant venture with the sister of the late reputed mob hit man Anthony “Tough Tony” Calabrese.
“You ask me what my association with the Outfit is,” Anglin says. “Well, to me, it’s none. I did business with them.”
He says that, since he’s been out of prison, some Outfit guys have reached out to him.
“I’ve had a few messages sent to me from the guys saying, you know, ‘Congratulations on getting out,’ ‘best wishes,’ things of that nature,” he says. “I have not responded to any of them. I don’t plan on it. There’s really nothing to communicate with them anymore.”
Anglin says he was always a “stand-up” guy, refusing to help the FBI prosecute Outfit bosses.
Anglin says Vrdolyak urged him to run for a seat in the Illinois House of Representatives. Anglin won the Republican primary in 1994 but lost in the general election.
It was more than a decade afterwards that Anglin’s property deals landed him in prison. He was convicted of bilking dozens of people out of more than $10 million between 2004 and 2006. The scheme worked like this: He advertised in newspapers to find investors to buy securities that supposedly were backed by real estate. Sometimes, though, the property didn’t exist. Other times, the buildings were little more than abandoned structures, according to prosecutors.
They said Anglin ran a Ponzi scheme in which early investors were paid off with money put in by later investors, who then were left with nothing.
Anglin didn’t admit guilt but accepted a conviction. He says prosecutors exaggerated his investors’ losses, which he pegs at around $5 million — about half of what he was accused of stealing.
For more than four years, Anglin was held at the Metropolitan Correctional Center in downtown Chicago as he awaited trial. He says he hung out with Marcello and other mobsters in the federal high-rise jail. Marcello “had a lot of power” in the jail, according to Anglin.
“I was given a television chair next to him, which is unheard of, and I watched a lot of baseball and comedies with him,” Anglin says. “Him and I would eat dinner every night together. We did not eat the food they gave us. We ate a lot of pizza.
“It was easy to get things like cellphones, drugs, liquor, etc.,” he says. “For me, it was phones and food I wanted. I had an endless supply of beef and meatball sandwiches and pizza coming to me. The guards there are on the take, big time, and you can own one for just a few thousand dollars.”
Anglin says Marcello warned him not to play poker with inmates who weren’t in their inner circle. “He looks me in the eye and says, ‘We do not play poker with these people. If they do not pay, we have no choice but to resolve the issue, and right now we have too many issues.’
“I am 6 feet tall and was 300 pounds at the time, and here he is, about 5-foot-6 and 165, and some say it’s fear, some say it’s respect, but everyone just listens to him,” Anglin says.
In 2010, Anglin was sent to prison. He says he spent a lot of his time there — first in Minnesota and later in Colorado — studying the law and helping inmates with their appeals.
“I called it Burrito Law,” he says. “Guys kept wanting to feed me burritos, thanking me.”
Anglin calculates that his work led to inmates getting a combined 224 years knocked off their sentences.
One inmate he helped was Stacey Peltier, who was serving a 292-month sentence for possession of a gun and drugs when he met Anglin in prison in Minnesota. Anglin researched Peltier’s case and thought he’d been wrongly sentenced as an armed career criminal. Peltier filed an appeal and was freed from prison in May 2017, getting seven years shaved off his sentence, court records show.
“Lee was better at the legal jargon than I was,” Peltier says from his home in North Dakota. “I kept trying myself but could not get the courts to agree with me.
“He is one of my best friends now,” Peltier says. “If it wasn’t for him, I’d still be sitting in there.”
He says that he and Anglin worked together to try to ease the racial tensions among inmates.
“He organized the whites, and I organized the natives,” says Peltier. “The natives and the Spanish stick together. We would squash a lot of stuff.”
Scott Carlberg, the “Time Bandit” convicted of robbing banks in Chicago’s south suburbs, says Anglin also helped keep the peace at the Metropolitan Correctional Center before he went to prison.
“One of the most endearing qualities about Lee was his uncanny ability to navigate to less tumultuous and safer waters,” Carlberg says by email from prison.
Carlberg says he passed messages between Anglin and Marcello in the downtown Chicago jail.
“I can tell you Mr. Marcello holds Lee in the highest esteem,” says Carlberg, who was dubbed the Time Bandit because he would order tellers to count to 300 before calling the police.
Now that Anglin is free, he vows to repay his victims, some of whom have expressed anger at him in letters filed in federal court. In one, written in 2009, a victim said Anglin was an “entrepreneur, thief [and] liar” who was “preying on honest folk.”
The man said, “I had to go back to square one and I was in the financial poor house.”
He wrote that he “would greatly appreciate recouping my financial loss.”
Anglin insists that’s going to happen.
“I have no worries about paying it back,” he says.
And: “I will continue with investments.”
He says he has stayed in touch with some of his investors and that some want to continue to do business with him.
He says the government froze millions of dollars of his assets and that he hopes to negotiate a settlement to recover some of that in September after completing a drug-counseling program.
Anglin says he’ll also continue to help hundreds of inmates with their legal problems. He plans to work for his former attorney Gerardo Gutierrez, who says he’ll be a clerk in his office.
“I like Lee and am willing to help him in any way I can,” Gutierrez says, noting that Anglin needs a job as a condition of his probation.
Eventually, Anglin says he might try to take the bar exam and become a lawyer, though he recognizes that, as tough as that would be without going to law school, he might have a bigger problem with the requirement that he’d need to show he’s a person of “good moral character.”
Asked about that, Gutierrez says, “I never shoot down a person’s dreams. There are people who have committed felonious crimes, turned their lives around and have gone on to become lawyers. It’s not impossible but very improbable.”
More than anything, Anglin says, he wants to be a family man. He says he plans to move with fiancée Jenni West to Utah one day.
“Being dragged through everything helped change who I am,” Anglin says. “It certainly humbles you a lot.
“I’m a different person now. I want to be home. I want to enjoy family. I want peace and quiet. I don’t want to be running nightclubs and owning them and hanging out in them. I don’t want to be having backroom meetings and exchanging envelopes and dealing with, you know, illegal gambling and all those things. I’m done with all that.”
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