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When titans Barry Sternlicht and Stephen Hanson began clashing over how to run BR Guest Hospitality, Mr. Sternlicht quietly began casting around for a new chief executive for the restaurant company.

In June 2013, the investment banker hired James Gersten, a veteran restaurateur, as a senior vice president overseeing hospitality for his growing hotel portfolio—but he had bigger plans for him.

"I thought James could take over BR Guest when I hired him," said Mr. Sternlicht, chief executive of Starwood Capital Group, the private-equity firm that owns BR Guest, operator of such well-known eateries as Dos Caminos, Blue Water Grill and Strip House. "You always have to have a backup plan," he added.

It took just seven months for Mr. Sternlicht's strategy to play out as he cleared the runway for Mr. Gersten by making Mr. Hanson an offer he couldn't refuse.

"I was paid to leave," said Mr. Hanson, who owned 50% of BR Guest and in December 2013 walked away from the company he launched 27 years earlier. He did not reveal his windfall, but said it "could not have been fairer." In fact, Mr. Hanson is busy hatching his next business plan.

Mr. Gersten, 45, who had been a director of the restaurant company from the moment he joined Starwood, was named chief executive, setting in motion an ambitious $15 million plan to expand and revamp BR Guest's 24 restaurants for a sale. It will be the second time Mr. Sternlicht has tried to unload BR Guest.

The company's troubles began almost immediately after Starwood Capital paid an eye-popping $150 million to acquire a 50% stake in 2007.

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