‘Craigslist Mobster’ Shows Major Pitfall of Choosing ‘The Life’

DeGerolamo, at 66, a career Lucchese associate,
wears results of latest would-be heist
If you are 66 years old and still an associate in a mob family –  it’s probably time to change professions. In fact, it was probably time to change professions 30 years ago. I mean, if you're not even a made guy by 66, but still a struggling associate, is it really worth it?

If Gerard DeGerolamo, the now-dubbed 'Craigslist Mobster,' had held down a regular job, he wouldn't have to waste his time now developing needlessly complicated, low-pay-off cons that probably aggravate his arthritis. He would get Social Security and maybe what’s left of any 401k plans or other investments he accrued over the decades of his career. He wouldn't have gotten arrested waving a can of mace while trying to rob a 31 year old  -- a 31 year old who had the guts to stand his ground and fight back, giving DeGerolamo a pretty good beating for his troubles.

Jimmy Breslin, in "The Good Rat," wrote about how "the life" treats older mobsters, guys past their earning prime, who mostly sit around and drink coffee -- and not even in their old social clubs, which the law closed down on them years ago. "Tony Cafe" is the name he uses for one of the mob bosses on the street today, or at least he was a few years ago when Breslin spoke with him.

Tony Cafe was actually pick-pocketed by a streetwalker -- a prostitute. Mob bosses, no matter how old they were, used to be universally known and respected, at least in their own neighborhoods, and Tony Cafe gets robbed on the street. In the book, there is also a scene with Tony and his cronies complaining about money, how much they had to spend on lawyers, how the government denied them social security. One veteran was even denied his VA payments. These guys -- who were all made, by the way -- were mostly living with relatives, their mothers, their wives.

Two things about mobsters: they would rather do time than spend a minute doing honest work, and they spend money like water, on clothes, on meals -- and on bills, too, as well as the typical expenses we civilians have to deal with.

Not that some of them don't try to plan for their retirement.

Joe Watts, the former Gotti crony I wrote about recently, 10 years ago, at the age of 59, was planning to retire to an eight-mile-long barrier island in the Florida Keys where he allegedly owned two luxurious homes (listed in the names of others, of course.)

The homes were worth an estimated $4 to $5 million and were on Casey Key, an island of 340 or so million-dollar homes, according to an article on ganglandnews.com. But Watts had to say bye-bye to his retirement paradise. Gangsters don't get to retire the way stockbrokers do, not when there are so many levels of law enforcement looking for something to do, like dig up more dirt on old mobsters to make sure they do life -- on the installment plan, if necessary.

Watts wasn't made, but only because he was a non-Italian. Otherwise he was highly respected and made wealthy from the high-level rackets Gambino bosses shared with him. What is DeGerolamo's excuse?

Here's the 66-year-old low-level associate's story as related in an article in the Daily News:

A 66-year-old con man was sentenced to 5 1/2 years in prison Tuesday for trying to swipe a $30,000 engagement ring from a man selling it on Craigslist.

Gerald DeGerolamo proclaimed his innocence.

"I never hurt anybody in my life," DeGerolamo, a Vietnam veteran, insisted to Manhattan Supreme Court Justice Thomas Farber. "To this day, I can't believe I was convicted."

"Preposterous," Farber said before handing down the prison term that will be followed by five years probation.

DeGerolamo - who served a decade in jail for a $3 million heist in the '90s - was found guilty by a Manhattan jury of grand larceny for a December 2009 West Village assault on jilted groom David Cushman.

Cushman was trying to sell a copy of a Tiffany Legacy ring through a classified ad posting on the internet.

"I was desperate because I was broken-hearted," Cushman said. "I felt that getting rid of the ring was like getting rid of the broken engagement."

Cushman said he met with DeGerolamo to show him the ring and the meeting turned into a violent struggle - DeGerolamo sprayed him with mace, shoved him and tried to grab the ring.

DeGerolamo, who sported bandages on his head after his arrest, claimed Cushman attacked him.

DeGerolamo, who faced up to 15 years in prison, is due back in court next month on charges he stole two diamond rings, worth $75,000, from a woman who was getting a divorce.

She also posted ads for her valuables online. (End of News story.)

The Post added more color to the story:

Ring Worm (as the article calls him) had repeatedly emailed and met with the lovelorn bachelor for weeks, each time insisting he was really, really on the verge of coughing up $30,000 to buy the ring.

Finally, in Dec., 2009, DeGerolamo, 66, lured the victim, salesman David Cushman, 31, to a vestibule on Christopher Street, on the pretext of meeting there with DeGerolamo's "daughter."

Once in the vestibule, DeGerolamo whipped out a can of Mace, blasted Cushman in the face, and grabbed the ring box.

Nearly blinded, with his face burning, Cushman still managed to turn the tables.

Cushman testified at trial last month that he chased the thug back out the door, tackling him, taking back the ring and delivering a sound beating that sent DeGerolamo to the hospital for facial stitches.

"He got the worst of it," defense lawyer Martin Morris told Manhattan Supreme Court Justice Thomas Farber, in asking for less time than the eight-year sentence requested by prosecutors. ...

DeGerolamo's rap sheet shows he has a flair for elaborate, wacky and ultimately failed criminal plots.

In 1989, DeGerolamo, his son, and another accomplice stole $3.7 million by taking off in an armored car he'd been hired to drive. The following year, he absconded off the grounds of a minimum-security federal prison.

In 1992, he and two associates were caught in the midst of yet another armored car heist -- in which the smallest of the trio was hidden in a packing crate to gain entrance into a cash-filled vault. He served a decade behind bars for that crime.

He remains charged with a second Craigslist attempted robbery -- this one of a 33-year-old woman selling two diamond rings that her husband, who she was divorcing, had given her.

That case is back before the same judge next month. (End of Post story.)

Now I am not a betting man, but I wouldn't be surprised if DeGerolamo--at least a small part of him--appreciates the time in the can -- it's probably like a vacation for him. He doesn't have to earn. And, at least if he ends up on the street at a later point in life, he can easily get himself arrested and spend the rest of his days with a roof over his head and three squares a day, maybe even some television.