As spring approached in 1925, the Pittsburgh Daily Post warned its readers: “Fainting Bertha,” member of the most despised fraternity of lawbreakers, would soon be stalking victims in the Golden Triangle.
Fear of this woman with an odd nickname kept authorities awake at night. Infamous as one of the “yellow dogs” of crime, Fainting Bertha, aka Margaret Reilly, never drove a knife into anyone’s torso or put a bullet in a poor soul’s brain.
No, much worse. Fainting Bertha was a pickpocket.
Here in the ‘Burgh, we’re obsessed with wallet-lifters. The Pittsburgh Press called them “rats,” hated even by other criminals. “A good burglar, stickup man or safe-blower would sooner fondle a rattlesnake than have it known he ever numbered a ‘cannon’ (as pickpockets were known) among his associates,” the Press wrote in 1927.
Pittsburgh newspapers considered it a civic duty to show readers the methods utilized by professional “dips.” A Post-Gazette photo file labeled “Pickpockets” contains several pictures of city detectives awkwardly and sometimes comically demonstrating various methods of thievery. Accompanying stories, which offered blow-by-blow accounts a typical pickpocket operation, certainly alerted readers, though we couldn’t help but notice the articles also served as textbooks for aspiring thieves.
Pickpockets in the 20s and 30s wore suits and ties and sported fedoras or straw hats on their heads. They were a stern, unsmiling and rather mean-looking crew. We know this because our files contain dozens of pickpocket mug shots. These guys look like they stepped out of a James Cagney gangster movie.
This was the golden era of pickpockets, a time when thieves acquired magnificent nicknames. Lurking along Pittsburgh’s sidewalks were criminals like Crooked Neck Smitty, Shoe String Kid, Knee Pants Kid (he stood 5-foot-2), Silent Sam, Silk Hat Harry and Sleepy City Jake.
Then there was Fainting Bertha. She earned her moniker by feigning illness and collapsing during court appearances. The act often kept her out of the pokey. Her arrest record dated to 1923, when she was picked up in a Downtown department store on suspicion she’d lifted thousands of dollars in cash.
“Clothed in the latest style garments and maintaining a dignity that was astounding,” wrote the Daily Post, “detectives thought they had made a mistake, but when they noticed the English accent of their prisoner, they concluded to take her to headquarters for questioning.”
We found no stories indicating Fainting Bertha was British, mind you. Nor could we determine why speaking with an “English accent” would render someone “suspicious” in the eyes of a Pittsburgh police detective.
Umbrella Jack gained fame by dropping lifted wallets into a folded canopy. Praying Emma invited holy retribution by preying upon kneeling church-goers. Scissors Mary carried snub-nosed clippers to snip purse handles and make off with entire handbags.
Many pickpockets were transient — they moved between East Coast cities and Chicago; Pittsburgh was simply a stop along the way. Others followed a bird-like pattern, migrating north when the weather warmed and victims gathered at carnivals and circuses.
Pickpockets loved the holidays, when gullible “suckers” loaded with cash squeezed into trolleys and department stores. Police responded in 1940 by assigning twenty detectives to protect the wallets and purses of Christmas shoppers in the Golden Triangle.
“The lads on the pickpocket detail were chosen because of their memory for faces,” reported the Post-Gazette. “Each spent a few hours each week studying 3,000 mug shots of convicted con men and leather lifters.”
Pittsburgh tried to make life difficult for dips by passing a law allowing magistrates to sentence known pickpockets to three months of hard labor without the option of paying a fine. “This sentence can be carried out regardless of whether the thief has committed a crime or not,” The Pittsburgh Press wrote in 1927. “The law merely requires that he be seen in a crowd or any place where the public congregates.”
The newspaper admitted questions about the law’s constitutionality, but wrote that no one had been tempted to test a statute aimed squarely at the rats of the underworld.
Our city’s obsession with pickpockets continued for several decades. The Pittsburgh Press devoted a portion of Roto Magazine in February 1973 to yet another story and photo layout explaining the manner in which a team of pickpockets set up and then fleeced the unsuspecting.
It wasn’t the same, though. The only nickname we found in the story was “Jostling Jerry.”
