J. Crew, Michelle Obama’s sometime clothing retailer, is yet another struggling private equity buyout. J. Crew’s owners, TPG Capital and Leonard Green & Partners, are stuck, tied to the bargain they struck with the company’s chief executive, Millard S. Drexler. Call it the “great man” problem.

J. Crew went private in 2011 in a $3 billion deal that was controversial because of Mr. Drexler’s actions. He began discussing a buyout with the two private equity groups and waited seven weeks before informing the company’s board. Mr. Drexler then refused to consider a buyout with another party. To cap it off, the two private equity firms lowered the price they were willing to pay at the last minute, a move supported by Mr. Drexler.

Mr. Drexler’s actions led to a bit of an outcry that he was abusing his position to engineer an acquisition of the company and force J. Crew’s shareholders into a deal with him alone. Not only that, but Mr. Drexler was teaming up with TPG, which had previously taken the company private and had recruited Mr. Drexler as chief executive.

It was also a testament to the “great man” theory of business. Mr. Drexler is a retail legend — the man who made the Gap into the Gap and, after being fired, the one who turned the same trick of creating a well-known fashion brand out of J. Crew. Because Mr. Drexler built J. Crew, the theory goes, he was the only one who could run it, leaving the board with no choice but to sell despite Mr. Drexler’s machinations.