Sir Kyffin Simpson, a self-made billionaire from Barbados, is on the brink of a monumental victory in his ongoing battle for control of Parkland Corp., the Calgary-based powerhouse that operates 4,000 gas stations and On the Run convenience stores.

Next week's annual meeting could see Simpson's handpicked directors take over the board, a move that has already garnered backing from influential shareholder advisory firms. If successful, the shake-up will likely lead to the ousting of long-standing CEO Bob Espey, paving the way for significant changes in the company that owns notable brands like Esso and Chevron.

Simpson's family-owned company, Simpson Oil Ltd., announced that over 60% of Parkland shareholders support its director nominations. This endorsement signals a possible board majority for Simpson, who, despite holding a hefty 19.8% stake in Parkland—worth approximately $1.2 billion—has had limited influence until now.

The tension stems from an earlier agreement that kept Simpson Oil on the sidelines. Until February, the billionaire's stake was muted by a standstill agreement linked to the sale of Caribbean gas stations that netted $2.35 billion in cash and Parkland shares. But a recent Ontario Supreme Court ruling has restored his activist rights and reignited his ambitions.

Now, Simpson’s proposed board slate, which includes nine nominees, is pushing back against Espey’s leadership, citing years of underperformance, missed targets, and a poorly executed M&A strategy as reasons for change.

A Strategic Redirection?

Last year's appointment of veteran oil executive Michael Jennings as chair has not quelled the discord. Jennings has expressed frustration over failed governance negotiations with Simpson Oil, stating, "The message back has always been one of control." As tensions rise, Parkland's strategic review conducted by investment banks could pave the way for potential sale discussions.

Interestingly, Parkland recently turned down an $8 billion takeover bid from Sunoco LP, indicating its reluctance to part with the company despite potential interest from Simpson Oil for such a deal.

A Legacy in Transition

Simpson made headlines more than just for his corporate maneuvers. Known as Caribbean royalty and an evangelical Christian, he built his empire from humble beginnings—transitioning from managing a single Texaco station in Barbados to becoming a titan in the fuel distribution sector. His business acumen is evident in his recent strategic moves to cash in on past successes.

With significant support from proxy advisory firms like Glass Lewis and Institutional Shareholder Services, the momentum appears to be shifting in Simpson's favor. Both firms have critiqued Parkland's stagnant stock performance and lack of proactive governance.

As the dynamics within Parkland shift, all eyes will be on Tuesday's annual meeting—a decisive moment that could redefine the future of one of Canada’s largest retail chains.