“What the hell is Gary doing down there?” a Wall Street source asked me, referring to Donald Trump’s chief economic adviser, Gary Cohn. It’s the same question I asked myself last week, when the president turned a press conference about infrastructure into an impromptu defense of a white supremacist mob that descended on Charlottesville, Virginia, to protest the proposed removal of a Confederate statue. Cohn, who took the lectern afterward in a failed attempt to steer the conversation back to potholes and the federal permitting process, looked shaken. The former Goldman Sachs president, who is Jewish, was “disgusted” and “upset,” according to people close to him. Another old Washington hand told me that Cohn had planned to resign last Friday but held off when White House strategist Stephen Bannon, who reportedly encouraged Trump’s comments, stepped down first. He still has not decided what to do. (A White House spokesman declined to comment.)

A New York Democrat with a long history of supporting Jewish charities, Cohn was always an odd fit with Trump, whose campaign ran an ad targeting his former boss, Goldman Sachs C.E.O. Lloyd Blankfein, that the Anti-Defamation League denounced as anti-Semitic. The Hillel building at Kent State University is named after Cohn and his wife, who has also served on the board of Planned Parenthood, and both are major donors to the Jewish Federation of Palm Beach County. But he is probably feeling heartened by Bannon’s departure, which has tipped the scales within the West Wing from the so-called “nationalist” wing to the “globalist” group, comprised of himself, Jared Kushner, and Ivanka Trump, who are also Jewish, as well as National Security Adviser H.R. McMaster and his deputy, Dina Powell. Now, the so-called globalists are in charge. “They feel like they are making a difference, right?” said a person who knows Cohn and Powell well. “They can’t control what comes out of the president’s mouth—and he’s saying a lot of stupid stuff —but they do feel like they are making headway versus the nationalists.” He said they feel like they have a “better chance of succeeding” now with their agenda, “but you could argue, ‘What does success look like?’”

That is the problem for Cohn, who has a flair for taking risks. “I always saw 95 percent of my great decisions start out as bad decisions,” he told students at American University, his alma mater, in 2009, at the height of the financial crisis. And remaining by Trump’s side, after an illustrious career on Wall Street, is his riskiest bet yet. On the one hand, with the departures of Bannon, Reince Priebus, and Sean Spicer, he might think he has gained an advantage in the never-ending battle for Trump’s ear. On the other hand, that thinking ignores the ongoing presence of a few lesser lights on the nationalist team—Sebastian Gorka, Stephen Miller, and Peter Navarro—and the fact that Trump never wants anyone to think he is listening to them instead of someone else. At stake is Cohn’s hope that Trump will name him chairman of the Federal Reserve, replacing Janet Yellen when her term expires next February.

But this is likely a bad long-term play for Cohn. He may have won the latest battle, but he surely has lost quite a few other skirmishes too: against his wishes, Trump excised the country from the Paris climate accord and persists in trying to impose some sort of cockamamie immigration ban. Meanwhile, large-scale legislative wins, such as reforming the tax code, are looking more and more elusive every day. And Yellen’s term isn’t up until six months from now; much can happen between now and then in Trumpworld. The very fact that Cohn has let it be known that he wants the job—Trump appointed him head of the search committee—is probably reason enough for Trump not to give it to him. Who ever gets what they are hoping for, or what they deserve, when Donald Trump is the decider?

The irony for Cohn is that he made his bones at Goldman as a shrewd risk taker. For instance, as the financial crisis was unfolding, he was clever enough to urge Goldman to not only short the housing market as a proprietary firm bet but also to sell down Goldman’s inventory of squirrelly mortgage-backed securities, regardless of the prices they would fetch. It was a brilliant move. Whatever Goldman lost by selling its mortgage securities at a loss throughout the first half of 2007 was more than made up for by what Goldman made in the second half of 2007 by shorting the mortgage market. Not for nothing was Cohn paid some $70 million in compensation in 2007.