Hamilton’s Boardwalk Empire

Annie Newman tries to hide her face from photographers as she is led off to prison. (Trevor Cole photo)

Back in the wild days of Prohibition, Hamilton, Ont., gangster Rocco Perri used to call himself the “King of the Bootleggers,” because he was so successful at getting illegal alcohol to thirsty people throughout Ontario.

He made a fortune in bootlegging, gambling, prostitution and drug smuggling, and owed a large part of his success to a pair of remarkable Jewish women who helped run his rackets.

In an age when opportunities for women were, for the most part, rigidly constrained, Besha (Bessie) Starkman and Annie Newman saw in the little Italian criminal a chance to earn more money than they ever imagined growing up poor and Jewish in Toronto.

Their lives have been captured in author Trevor Cole’s book, The Whiskey King, a tale he shared with the local chapter of Na’amat Canada last month.

In an interview with The CJN ahead of his presentation, Cole said that while there’s room for some debate over the claims that Starkman and Newman were the “brains” behind Perri’s gang, it’s clear that they brought skills to the crime world that Perri lacked.

“I think it’s clear Rocco would not have been nearly as successful as he was without Bessie and Annie,” Cole said. “Bessie saw advantages and business opportunities that Rocco might not have seen on his own.”

As bootleggers, Cole said, “Rocco had the network of men they needed for distribution and enforcement, but Bessie understood business. She advised him, encouraged him and facilitated a lot of what he did. She had an innate understanding of how to take advantage of certain situations.”

Those qualities of Starkman’s emerged most fully when the end of Prohibition forced the Perri gang to look for new revenue streams – finding them in the growing field of narcotics smuggling.

“People have a kind of romantic view that Bessie was responsible for much of what they did in bootlegging, but it’s certainly clear that she was responsible for the narcotics traffic,” Cole said. “That was her impetus, it was her baby.”


Starkman was born in Poland in 1889 and arrived in Canada with her family sometime around 1900. She married at age 18, had two daughters and then, in 1912, decided to abandon them and run off with an Italian boarder she and her husband had taken in.

From then, until she was murdered in 1930 in an assassination in which some say Perri helped orchestrate, she lived a life that was unknown to poor Jewish immigrants.

“Bessie was a somewhat vain woman who was somewhat ruthless but undoubtedly very smart,” Cole said. “She was someone who loved diamonds and saw the benefits of wealth. She liked expensive clothes and diamonds and liked to show them off in a way Rocco didn’t.”

Starkman’s criminal career ended suddenly on Aug. 13, 1930. She and Perri pulled into the garage of their mansion and she stepped out of their car and into a pair of shotgun blasts.

That death, and the way she lived her life, caused serious debate in Hamilton’s Jewish community – to the point where the rabbi of the city’s now-defunct Hess Street shul refused to bury her. A visiting rabbi who had once lived in the city was drafted to oversee the service.

The death of his long-time partner seemed to deflate Perri.

“He seemed to lose his mojo after that. He just wasn’t the same,” Cole said, adding that the hood’s spirits didn’t start to revive until he met another Jewish woman from Toronto and brought her back to Hamilton.

“It’s not really clear how he met Annie, but he immediately saw in her Bessie 2.0,” Cole said. “Annie was just as corrupt and business-like as Bessie.”

Cole said little is known about Newman’s background, where she was born or her life before and after Rocco Perri. She was short and buxom, a platinum blonde who seemed to pour most of her affection into a little Pomeranian she named Fifi.

Together, the new criminal power couple bootlegged liquor, sold drugs and made money from other illegal enterprises, but their time together was short. In 1943, Newman went to prison on a gold-smuggling conviction and the next year, Perri was visiting a cousin in Hamilton when he complained of a headache and went for a walk to clear his head. He was never seen again.

While local legend holds that he “sleeps with the fishes” in a cement-filled barrel at the bottom of Hamilton harbour, a more recent theory, backed by a letter he allegedly wrote a cousin in the 1950s, holds that he moved to a small New York town and lived out his days in obscurity.

Whichever fate befell him, Perri never reunited with Newman. She served her prison sentence, returned to Hamilton and sold their fancy home. Cole said he didn’t research her life after Perri, but one source says she married twice and died in 1974 at age 85.