Al U., better known as “Chicago Al”, likes to gamble. Scratch that. He loves to gamble—Al claims that his longest gambling streak lasted 22,000 days. That’s over 60 years. Now, for the first time in his life, the 72-year-old resident of Beit T’Shuvah has finally laid down the cards and horse-betting for one final gamble: a shot at redemption.
The son of a doctor and a college professor, Al was raised Jewish and had a seemingly idyllic childhood. He was born in Chicago and moved to El Paso when his father was called there for the army in 1953. He played tennis and the bassoon and was a natural at academics. “I was in the top 2% of my high school class, and I didn’t study. I played tennis every day. And baseball. I was a model student,” he says. Precocious and clever, young Al found a new way to put his intellect and craving for excitement into practice. When Al first started gambling, he quickly realized that he was very good at cards and rarely lost. Compared to the alcoholic, Al’s addiction was harder to spot. “You never knew what I was,” he reflects.
Al’s good marks earned him a scholarship to the University of Texas. But instead of El Paso, Al went to Mexico and supported his education by paying other students to attend classes for him. Al’s academic standing was important to him and was his main financial priority.
To fund his hired student proxies, Al wrote a lot of bad checks. “A lot of bad checks got me into jail,” he smirks. Al forged tens of thousands of dollars, but what landed him in jail the first time was a measly fifty dollar check. Disapproving of his son’s behavior, Al’s dad arranged for him to go to prison when he was 20 years old. Al would end up going to prison a total of 11 times throughout his life. Al’s grifter lifestyle involved many hustles. His most peculiar – and most profitable – revolved around stamps. Al would walk into a store and purchase several thousands of dollars worth of postage, which he paid for with bad checks. Al would then peddle the stamps to his “connections” and sell them for around 85% of their value, netting him a sizable profit.
Over the years, Al would spend $100,000 on stamps, all funded with bad checks. “They were the easiest to carry around. Booze and gems were harder to take with me,” he says with a sly smile. As Al ventured deeper into the world of crime, he clung to the belief that he’d eventually be able to turn things around. “I always used my name and my real bank account because even though I was giving them a bad check, it was my hope that one day, I’d have money in my account to pay for them,” he explains.
Although Al’s hustles ultimately landed him behind bars, that didn’t mean he’d cleaned up his act. “I ran the prisons too. I didn’t run them physically, but I ran the gambling yard wherever I went,” he says. Al “booked the whole yard” i.e., he’d put out a ticket on a sports game and everybody would bet on it. One of his more lucrative schemes scored him $15,000 while locked up in Nevada. He spent part of the money hoarding soups, shampoos, and cigarettes in his locker and lending them out to other prisoners like a benevolent mafioso. A sucker for a good sob story, Al explains, “I didn’t like to charge interest or anything; I’m very easy going. I’m very generous. If somebody needed to have anything I’d give ‘em stuff. I still do.”
Al met his fair share of interesting characters while he was incarcerated. From sharing a wing with the Manson family’s Tex Watson to run-ins with members of the Aryan Brotherhood while he was locked up in San Quentin Prison, Al took everybody in stride. Even around the Aryan Brothers, Al refused to hide his Jewish heritage. “Most kids who were Jewish—and there weren’t many—wouldn’t say they were Jewish. They were scared. I wasn’t,” he explains. Al often acted as a Jewish spokesman, speaking to visiting rabbis on behalf of every Jewish inmate—despite the admission that he’s “not very learned.”
Al’s pride in his Jewish heritage and his on-and-off incarceration would eventually land him in the same room as Harriet Rossetto, Beit T’Shuvah’s fearless founder. Al met Harriet in county jail 35 years ago. She was working for Gateways Hospital and was sent to various jails to interview Jewish inmates. “She always talked about opening [Beit T’Shuvah]. It was a fantasy at that time,” he remembers. A few months later, he got out of jail and within a year helped Harriet open Beit T’Shuvah on Lake Street. “I was there when the ribbon was cut. We had a rabbi, a chef, and about six inmates,” he says. Al is thrilled that Harriet’s dream came true. “She’s a remarkable woman. Not many people have done what she does in the whole world,” he explains.
This is the first time Al has ever been to any kind of treatment center. Before coming to Beit T’Shuvah, he was living with his girlfriend in Indiana and collecting $700 a month in social security. When his girlfriend got sick, she was moved into a home and Al was left to fend for himself. He couldn’t afford to live. It was at this time that Harriet called Al. She had remained friends with Al’s sister who had informed Harriet of Al’s current lot in life. “She called me one day and said: ‘Come, you’re ready,’” he says. Al was indeed ready. He’d had enough.
Al has a lot to repair, financially and personally. He has no relationship with his kids or grandkids. As he explains, “I have an unusual past. I’m a gambler of big, big money, even though I never had big money. I stole it. I’ve hurt a lot of people. I’ve hurt a lot of businesses, and I regret that. I would never do it again.”
Today, Al is helping residents of Beit T’Shuvah write résumés, serving meat with Chicago flair, and he is still happy to give a spare five dollars to anybody with a good sob story. Al spends the entirety of his social security checks, every month, paying back his debts. Age doesn’t stop him. For the first time in his life, Al is betting on himself, and he’s all in.