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In ‘The Phelan Feud,’ Stephen Kimber Delves into a Canadian ‘Succession’ Story

The bitter family dispute over control of Cara Operations, a restaurant and catering behemoth, is rife with bad behaviour and unresolved conflict / BY Jennifer Wilson / June 6th, 2024


After two successful inter-generational transitions, you might assume the third-generation leader of a 100-year-old family business would be willing and able to manage his own succession. You would be wrong.  

In The Phelan Feud: The Bitter Struggle for Control of a Great Canadian Empire, award-winning Halifax writer, editor and broadcaster Stephen Kimber delivers a detailed account of a bitter dispute over control of Cara Operations, a family business known best for airport catering, Swiss Chalet and Harvey’s. The conflict embroiled three generations in decades of uncertainty, shifting loyalties, and – ultimately – ruined relationships.

As the author of 11 nonfiction books, ranging from a biography of NDP politician Alexa McDonough to a thriller about Cuban intelligence agents, Kimber loves exploring new topics and delving into the archival research required to present them thoroughly and accurately. “I don’t think of myself as a traditional business journalist,” Kimber says. “I didn’t know much about what was going on [with Cara] … So, I learned.”

 

Stephen Kimber

 

As a second-generation family business leader of The Canada Homestay Network, I was hooked from the opening scene. Kimber invites the reader into the elegant living room of the Phelan family home in Toronto on a spring morning in 1988, where a discussion about a surprising change to Paul James Phelan’s will was unfolding. Instead of dividing his voting shares (which effectively controlled Cara) equally among his progeny, the new will established a proxy committee made up of his son and two outside advisors. At times, the book reads like a real-life Canadian Succession story, complete with an ailing father, substance abuse and sibling rivalry. 

But it’s not all drama and tension. Kimber reviews the fascinating history of the first two generations in the business, taking the reader back to 1826 and the arrival in Montreal of orphaned Irish siblings, Mary and Thomas. Over time, four of their children ended up in business together. They began peddling apples and newspapers to steamship passengers in the 1850s, progressing to concessions on railroads throughout Canada. They incorporated Cara – originally known as the Canada Railway News Company – in 1883. Thomas Patrick (TP) Phelan, one of Cara’s founders and its president, was a natural entrepreneur and salesman. By 1895, he had begun Cara’s first restaurant in Gravenhurst, Ont., which, along with catering, would eventually become their main source of revenue.

When TP died, his brother-in-law briefly took over, followed by TP’s son. In those days, succession was determined by primogeniture: the practice of leaving the business to the first male child. Eventually, this logic, along with what Kimber describes as the “prevalence of substance abuse among family members and the cascading issues that that created,” were two of the key factors that lead to the Phelan family dysfunction. Yet even this is an oversimplified explanation for what happened. When it comes to families, there are never easy answers.

Paul James (PJ) Phelan, the third-generation leader who became president in 1961, was “in every way, the true successor to swashbuckling founder Thomas Patrick Phelan, and the man who would lead the company to its greatest successes,” Kimber writes. He portrays PJ as a complex character who, on the one hand, wasn’t ready or willing to let go. He caused an irreparable rift between his daughter, Gail, and his son, Paul David – the heir apparent – by inviting both of them into the business, but not creating a clear path for either of them to take over. He was also an alcoholic who never conceded he had a problem. On the other hand, “this was a man who had a thing about family,” Kimber says. “He was passionate about them working together. He’s not a sympathetic character in terms of what he did, but he’s sympathetic to me in terms of what he wanted.” 

Without a clear path to succession, trouble in the fourth generation seemed inevitable, but Paul David made it worse. “Paul David was an entitled guy,” Kimber says. “He was described by his father as a prince who would one day become king.” He was so certain of taking over his father’s throne that he spent more time outside the office than in it. In addition to commodity trading, he was devoted to sailing – a passion he shared with his father – and raced Finn class sailboats internationally, backed several teams in major competitions and financed sailing documentaries. At the same time, Kimber is quick to say that “it is important not to turn people into one-dimensional characters. I didn’t want the book to be a hatchet job on Paul David.” 

Gail and Rosemary Phelan, the sisters who ultimately assumed control of Cara along with their niece Holly, said they didn’t want that either. They wanted the story to be told – they commissioned the book, turned over their personal correspondence and introduced Kimber to several of the people he interviewed. 

 

Sisters Rosemary Phelan and Gail Regan savour the results of a 2004 vote that allowed Cara to go private after decades of being publicly traded. Photo: Tibor Kolley/Canadian Press

 

As much as Gail and Rosemary invited Kimber into their family’s history, Kimber acknowledges the process “stirred up a lot of stuff, especially for Rosemary.… For her, this was painful. I was putting her back through all this stuff in as much detail as she could manage.”

While The Phelan Feud is rife with bad behaviour and unresolved conflict, there is a triumph of sorts in the way Gail and Rosemary prevailed as women in business. PJ and his wife Helen couldn’t seem to imagine a place for their daughters in company leadership – partly due to their own views on gender roles, and partly because the question of suitability was blurry for both Gail and Paul David. At the same time, Helen had a public reputation as a feminist; she served on boards and was a prominent philanthropist in women’s health and the arts. Rosemary and Gail had a complicated relationship with their mother, but said she gave them the courage to challenge their brother and father. 

Are there lessons in this story? “I don’t know … other than not to do anything they did,” Kimber says with a laugh. But he does have a few parting thoughts. “There is this sense that the family business has to continue forever through the generations,” he says. “And yet, we know that the majority of businesses only last two or three years. A family business that lasts 25 or 30 years is a real accomplishment. The founders really have to step back and say, ‘What is in the best interest of the family, and the business?’” 

In my own case, my parents and I recently decided to hire non-family managers for our company. “That’s a right decision,” Kimber told me. “That allows you to be part of the business, but not day-to-day involved in it. The business dominated the Phelans’ lives. It owned them.” This story is not a teachable moment for most businesses. It’s more of a cautionary tale, but it’s certainly a fascinating one.

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