Why you should care

Because, apparently, there are plenty of second acts in American lives.

There’s always a piece of the immigrant story that’s absolutely present through its absence in almost any retelling of the immigrant story. Very simply it’s this: Despite all the present presidential chitchat about shithole countries, not many arrivals to these shores showed up rich. You showed up with what you brought, or with what brought you, and went forth and attempted to prosper. And for many, it wasn’t so much “poor” as it was “dirt poor.”

So when Macy Motie Friedman, born in 1898 on New York’s Lower East Side to parents from Eastern Europe, started stealing, he was just getting started. With an early stop that involved stealing from his father no less, Friedman then moved on to shoplifting bagels and whatever else he could get his hands on, including his new name, Morris “Red” Rudensky. That he stole from a neighborhood kid to draw a shorter jail sentence.

So not at all a shocker that by 1911, when he was 13 years old — after first being arrested at age 9 — he was deemed “incorrigible” and sent to a reformatory, aka a prison for kids. “Unless you’re a degenerate piece of shit, there are only three reasons why you choose crime,” says John Gotti defense attorney Bruce Cutler in a past tête-à-tête with us. “Poverty, despair and culture.” For Rudensky, while poverty might have fueled his frenzy for felony, ultimately it was something else that drove him to crime. Largely, and without many doubts, he was just too smart for his station in life.

His first escape, and it should be noted this was from Leavenworth prison, not a cakewalk by any stretch, came in a body bag with another body already in it. A dead one.

“People generally think it’s stupid kids who are getting arrested,” says Irma Norman, a longtime counselor at New York’s now-defunct Spofford Juvenile Detention Center. “You have those too, but lots of those kids are just not getting enough breaks fast enough.” With Rudensky, it was probably this and something else as well. He was just too smart to be OK with getting paid like he wasn’t.

So despite spending around 35 years in prison before all was said and done, Rudensky made his time out of prison pay as big as he could swing it. Initially by honing his skills at breaking into the places where the most money was kept — safes and lockboxes. But first, he had to break out of the reformatory, and he did so, with a quickness, and headed west to Chicago, where he found a home with Al Capone and Bugs Moran on the strength of his reputation for stealing.

A home that paid him well enough to buy a whorehouse in Chicago with $50,000 in stolen gold. A relatively modest strike compared to his heist of $2 million of seized liquor from a government warehouse. But because all good things come to an end, so it was that the 29-year-old Rudensky was back inside before too long and back to getting back outside before too long too. His first escape, and it should be noted this was from Leavenworth prison, not a cakewalk by any stretch, came in a body bag with another body already in it. A dead one.

Hours into his ride to freedom, Rudensky started bleeding. From his ears.

Though Rudensky was caught, it just wised him up, so much so that the next time, he shipped himself out of prison in a trunk instead of a body bag. Although he wrote “This Side Up” on the trunk, he nevertheless was loaded onto a service train and made it out of the prison upside down. All well and good for short trips, but despite trying to rock the trunk on its side, it had been wedged in tight, and hours into his ride to freedom, Rudensky started bleeding. From his ears. The blood flowing from the trunk tipped off the authorities, and this time around he ended up with a sentence that would give even the hardest of cases pause.

Which is where the real magic kicked in. After being taught to read and write in prison, he started publishing a prison newspaper and organizing prisoners to help in the war effort, for which he earned a commendation from President Franklin D. Roosevelt. He also happened to save the life of another prisoner during a prison riot. The ex-con, on release, ultimately became president of a large advertising firm that hired Rudensky when he got out of prison in 1944.

So from a copy editor at the ad agency, he went on to work at 3M, where he climbed the corporate ladder to become a chief security consultant, because who knew more about keeping stuff safe than a safecracker. Then, on a whim, he published a book in 1970, The Gonif (“thief” in Yiddish), which sold well. Rudensky, thick New York accent and all, became a national hit: TV talk shows, tours and a celebrity that lasted until he died at the age of 89 in 1988. Having successfully outlived his wife, his former cellmate Robert Stroud (the famous Birdman of Alcatraz) and another former cellmate, Capone. See, Rudensky had pulled the greatest escape of them all: He died a free man.

But insofar as all of the attention paid to his criminal exploits, Rudensky was unforgiving about himself. In an interview with journalist Al Aronowitz, he put a finer point on it. “It’s a lot of crap,” he said. “I’m not very proud of it. How can you be proud of a lousy life like that?”

OZYFlashback

Tales from the past to titillate and educate while giving you a lens on the present and future.