Donald Trump’s Mugshot a Great Addition to History of Distinctive Booking Photos

To commemorate POTUS’ instantly iconic shot, here are a few of my favorites.

Mugshots are like anything else – some people just instinctively know how to do ‘em right, others not so much.

President Trump took a beautiful, perfect mugshot in Atlanta the other night.

It got me to thinking about other memorable mugshots. I’ve been collecting them for decades, from all over New England.

To commemorate POTUS’ instantly iconic shot, here are a few of my favorites, some of which impart lessons for anyone who might someday have the misfortune of being lugged.

Gennaro “Jerry” Angiulo

Whitey Bulger

The bigger the hat, the bigger the hood. These are the two preeminent Boston mobsters of the late 20th century, in their early years – Gennaro “Jerry” Angiulo and Whitey Bulger.

Jimmy “the Bear” Flemmi

Jimmy “the Bear” Flemmi could have been posing for one of those “This is your mind on drugs!” posters when this 1979 prison mugshot was taken. He was the brother of Stevie Flemmi. The Bear died at MCI-Walpole a few months later – of a drug overdose.

Myer Sherman

Francis McPartland

Never let ’em see you sweat. Myer Sherman, busted on a gambling rap, seems to be wondering what his mother will think. Francis X. McPartland is just angry, even though he’s wearing that groovy shirt.

Toby Zimmerman Wagner

The bulls seldom let molls visit the powder room to freshen up. So Toby Zimmerman Wagner looked a little rough here. She would die in a 1963 shootout in Egleston Square that her wise-guy boyfriend had with the Boston cops.

J.R. Russo

Teddy Venus

Fashion statements: Mafia hitman J.R. Russo designed his own clothes, and he used this mugshot to strut his bespoke chapeau. Teddy Venus (real name Venios) ran “clubs” in the Combat Zone, but here oddly he’s going with that Somerset Club-style bow-tie look.

Bobo Petricone

You could learn from an unflattering mugshot. Winter Hill’s Bobo Petricone noticed that he was too fat, so when he fled to Hollywood, he took off 50 pounds, changed his name to “Alex Rocco” and then got the role of Moe Greene in The Godfather.

Carmen Gagliardi

You can never predict how far your mugshot will go. Gagliardi was a small-time hood, and he was barely awake when he got lugged in Malden in 1965. He didn’t care how wasted he looked. A couple years later, he was transporting the body of a Mafia hit victim to a shallow grave when the cops pulled over his car. He escaped, and ended up on the FBI’s Most Wanted List. His stupid photo ended up on every Post Office wall in all 50 states. Gags died of a drug overdose in prison in 1975.

Chico Amico

Peter Stenstrom

The Edd “Kookie” Brynes look was very big in the late 1950s. Of the two punks using that greasy kids’ stuff here, the better known was Chico Amico. He was executed by a Mafia hit squad outside Alphonse’s Broken Heart Lounge in Revere in 1966.

Paul James Botteri

Botteri, born in 1926, did not take direction well. Hey pal, look at the camera!

Francis J. Smith, Jr.

It probably wasn’t too difficult to pick Smith out of a lineup.

Milton Powers

In all his mugshots, Powers always went with the bleep-eating grin.

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