The CON-tessa

Article Overview: 

In the early 1970s, the worlds of organized crime and Toronto high society collided in a high-stakes game of international cat-and-mouse. Our key players? Ted Robertson, a seasoned DEA agent, masquerading as a corrupt union official, and Anna Von Bernadotte, a striking Canadian model with a mysterious European title that added just the right amount of mystery. When a tip leads Robertson to Anna’s opulent apartment, she is caught in a sting of her own making. This first blog post is her reimagined story.

The CON-tessa

by Suzen Fromstein

In the early 1970s, the world of organized crime and high society collide in a high-stakes game of deception. Ted Robertson, a veteran DEA agent from Chicago, and Anna Von Bernadotte, a striking Canadian model with a mysterious European title, were at the centre of this real-life sting operation.

In July 1972, one of Robertson’s regular informants tipped him off about a Canadian gang’s plans to establish a cocaine distribution network in Chicago. The informant had overheard this while attending a lavish party in a posh Toronto apartment hosted by one Lynda Anne MacIntosh, an attractive 6’2” former model with a claim to Swedish royalty, known publicly as Countess Anna Von Bernadotte.

Anna’s life of luxury stemmed from her relationship with Superior Court Judge Charles Pentland III, whom she met while working as a legal secretary for a prominent local criminal lawyer. The Swedish beauty quickly adapted to a storybook lifestyle that far surpassed her humble beginnings.

The couple resided in the judge’s upscale downtown Toronto apartment. Their public appearances were rare, limited mostly to outings at the opera, ballet, or charity events befitting the judge’s standing in the community. Most of their social life took place within the confines of their opulent home, where Anna, an exceptional cook, hosted intimate dinners.

When the Judge died of a heart attack three years into their common-law relationship, Anna had no intention of relinquishing the lavish lifestyle he had provided. With the judge’s reputation no longer a concern, Anna’s social circle expanded to include not just Canadian intellectuals, Olympiads, politicians, actors, and corporate titans, but also a more eclectic mix: astrologers and tarot card readers, boosters, pushers, and white collar criminals.

Among her new acquaintances was Giuseppe Luciano who became a close friend and mentor. “Big G” as Anna liked to call him, had a knack for delivering lucrative tips, including one about a Japanese carmaker developing a state-of-the art, energy-efficient vehicle – at a time when Canadian and US manufacturers had nothing to rival it. This tip, among others, was just the beginning.

Conning the Con

Coming from humble beginnings, the Countess understood the desire to elevate one’s status and often shared her latest stock tips with her confidants, who reciprocated with their own insider information.

One such exchange introduced her to MRI technology courtesy of a well-travelled Chicago businessman who often visited Toronto. Both Big G and the Countess profited handsomely from that tip, and they were always delighted to host him whenever his business brought him to the city.

During one of these gatherings, the Countess discreetly pulled the businessman aside and hinted at a lucrative business opportunity: a chance to buy unlimited quantities of a cocaine provided she could find the right distribution partner. “Maybe I can help,” the businessman offered.

Upon returning to Chicago, the businessman relayed the story to Robertson. Recognizing the potential, Robertson immediately requested an introduction as soon as possible and contacted the RCMP. It didn’t surprise him to learn that they had been wiretapping and bugging the Countess and Big G for over two years.

The next time the businessman was in Toronto, he arranges a private dinner at Barberiens Steak House to introduce Robertson, a big, brash Texan and an official of the Teamsters Union Pension Fund eager to make a fortune in the cocaine market to Anna.

Robertson played the role to perfection, flashing $50,000 in $100 bills and presenting cards and papers identifying him as a legitimate Teamsters official.

The evening passed smoothly, and the next day Robertson sent flowers to the Countess, thanking her for a delightful evening and expressing his eagerness to see her again, whether in Toronto or if she ever found herself in the Windy City.

The Sting

Over the next few months, the Countess and Robertson spoke on the telephone frequently, slowly building a foundation of trust. After several months, the Countess hinted that she had something important to discuss but was reluctant to share details over the phone. A man of action, Robertson sent her a plane ticket and they agreed to meet at a cocktail lounge near O’Hare International Airport.

During their meeting, the Countess made an interesting offer: her clients wanted to move 20 kg of cocaine every month and needed to know if Robertson could facilitate the distribution.

“That shouldn’t be a problem,” Robertson assured her, explaining that he could easily “maneuver the books around.” It was a plausible cover, especially given the scrutiny the International Teamsters Union was under for the mismanagement of its vast pension fund.

Despite his convincing performance, the Countess remained wary. She requested two random $100 bills, inspecting them closely by the flame of her gold Dunhill cigarette lighter. She admitted that while everything appeared legitimate, she wasn’t a currency expert and needed her client to verify the bills. Robertson, confident in his cover, smiled and agreed. Later that summer the Countess called to confirm that “her people” were ready to do business.

Sbortly thereafter, Robertson flew to Toronto to meet with the Countess again, this time at the Toronto International Airport lounge. She was accompanied by two burly, rough-around-the edges men, the twins Sunny and Franco Fiumara.

As they settled in, the Countess drops a bombshell – her client wasn’t interested in moving cocaine after all. Instead, they wanted to deal in an unlimited supply of 93% pure heroin from southern Italy, priced at $10,000 a kilogram. “That shouldn’t be a problem,” Robertson replied, maintaining his composure. However, before finalizing their arrangements, the Countess insisted that Robertson provide a reference – business was business, after all.

Without hesitation, Robertson replied, “Frank Lucas. The Manhattan heroin king. I’m assuming you know him. And, nothing personal, but I also need a reference.” Sunny smirked and said, “Franklin ‘Lefty’ Rosenthal. ‘Lefty’ handles the books at Chicago’s Stardust, Fremont, Marina and Hacienda casinos.”

Several months later, Countess Anna sold $20,000 worth of heroin to Robertson. As she turned to leave, the RCMP moved in. The woman who had charmed the upper echelons of society, and toyed with some of the most dangerous men in the world, was now a convicted felon. She served four years in the Kingston Penitentiary, where she exchanged a cold, gray cell for her posh Toronto apartment. After probabtion and because she didn’t reoffend her record was expunged.

After her death, investigators uncovered at least five other false identities – each with its own trail of social insurance numbers and credit cards. Anna’s entire life had been a masterclass in deception, her true identity hidden beneath layers of lies.

In a 2021 Psychology Today article, Rob Whitley, PhD, explains how individuals like Anna might construct such elaborate facades. He suggests that that when internal desires clash with lived reality, the result can be the creation of a “false self.” This false self may grant temporary solace, but it often leads to fractured identities and poor mental health.

Anna’s life was a dazzling illusion, but beneath the sparkle, she was lost – trapped in a web of her own making. Perhaps, in the end, like Anna, we are all at risk of losing ourselves in the stories we tell.