Many Leasiders know that Divadale Drive takes its name from the magnificent Bayview estate once owned and occupied in the late 1930s-early 1940s by the millionaire American oil executive and soldier of fortune, Captain James Flanagan (1872-1950). Flanagan named his residence “Divadale” after his daughter Diva. While his fabulous mansion is long gone, the street itself, originally called Mitchell Avenue, has flourished and kept Diva’s name alive. Who was this mysterious woman after whom one of North Leaside’s best-known boulevards is named?
Poor little rich girl
Diva Flanagan was born in Denver, Colorado on June 6, 1921. Her parents were incredibly wealthy, and she lacked for nothing while growing up. As a young girl, she attended elite boarding schools in California, Mississippi and Denver. When she was only seven, she accompanied her mother on a two-week trip to Hawaii. As a 15-year-old student in Mississippi, her father arranged for her to meet President Franklin D. Roosevelt as he travelled through the state.
Despite her privileged position, Diva’s life was far from ideal. Her parents divorced in 1927, and she spent much of the time away from home at school. In a gesture that suggests resentment, she reportedly changed her name from Hazel (her mother’s name) to Diva soon after their separation. When she wasn’t attending school, she lived in Denver with her mother and saw her father only occasionally throughout the 1930s.
Visits Toronto
By then, Captain Flanagan had moved to Toronto where he served as president of the Andian National Corporation, Limited and was busy developing oil production operations in South America. It was during this time that Diva would visit him – often with her mother, despite the divorce. One visit took place in early 1933, another in October 1934 and another in October 1938. She visited him again in May 1939 with her grandmother, when King George VI and Queen Elizabeth came to Toronto. Captain Flanagan, who had amazing connections, arranged for them to meet the royal couple. Soon after arriving at Divadale, however, Diva’s grandmother died of a heart attack and the meeting presumably never took place.
A disastrous marriage
After graduating from the University of Denver in 1944, Diva went to live with her father in Palm Beach. The captain had sold Divadale and now resided in Florida. It was there that she met Anthony John Bittson, who was almost 30 years her senior, was married previously and had a child. A successful engineer and “exporter,” he also claimed to be a Russian prince who had personally known Rasputin, Trotsky, Lenin and Stalin. Diva fell madly in love. She married Bittson in April 1945, less than four months after meeting and despite strong opposition from her father.
The couple settled in affluent Great Neck, Long Island and by 1951 had two children – both boys. During that time, Captain Flanagan died, leaving 60 per cent of his vast fortune to Diva. She was now a very wealthy woman. Soon afterwards the marital problems started.
By September 1953, the couple had already separated following an argument during which Bittson assaulted Diva as she was trying to leave their house. Weeks later, despite a restraining order, he took their two boys and flew with them to Lisbon, Portugal. For the next several years, Diva pursued a protracted court battle for custody. She eventually moved to Lisbon in the mid-1950s to be closer to her children whom the Portuguese courts had placed under third-party protection. She died there in 1962 at age 41. The death certificate listed pneumonia as the cause, but there were rumours that foul play may have been a factor.
Thus ended the troubled, tumultuous life of Diva Flanagan Bittson – the poor little rich girl who gave her name to a Leaside street.2
1 See Jeanne Hopkins, “Divadale Drive,” Leaside Life January 2018.
2 Sources consulted for this article consisted of online primary and secondary material available through such outlets as the Toronto Public Library and ancestry.com. The author would also like to thank Mitch Bubulj for providing important observations contributing to this article.
