Stephen Squeri appeared to check all the boxes as the next CEO of American Express. By 2016 he had spent three decades at the credit card colossus, reshaped tech operations, headed the corporate and merchant franchises, and orchestrated a spectacularly successful restructuring. But the Queens, N.Y., native had a giant liability in his quest to succeed the crisply tailored, cuff-link-sporting Ken Chenault: He didn’t dress like a Wall Street CEO.
A year or two earlier, Squeri had appeared at a board meeting, held during a New York Jets playoff game, wearing his lucky Curtis Martin jersey under a suit jacket as a “go get ’em” shout-out to his prized team. “Some directors were a bit put off,” he told Fortune. “People judged a book by its cover, and my cover wasn’t all that good.” Coworkers took notice as well. Years earlier, recalls Squeri, “one fellow manager asked me, ‘Where did you get that suit?’ and I said, ‘I’ve got five more just like it I bought for a couple hundred dollars, total.’” The colleague’s rejoinder: “Therein lies the problem.”
