Grand Cayman, the largest of the Cayman Islands, is distinguished by a crescent-shaped, white-sand beach lined with four- and five-star hotels, dive shops, and stores selling luxury goods at a price point you might expect in the Zurich airport. Two of the most popular activities are swimming with stingrays and operating offshore tax havens. It is also a favored destination for corporate retreats, and for four days this April more than five hundred financial compliance officers converged on the Ritz-Carlton in Grand Cayman. Between sets of tennis, rounds of golf, and seminars on operational due diligence and cash-management efficiencies, it became clear that some of them were a little nervous about their futures. Compliance officers are supposed to keep banks, hedge funds, and other companies out of trouble. Doing so sometimes means telling powerful money-makers that they have to follow rules, which might mean that they make less money. This is not always an easy task. For every insider-trading arrest, fake-account scandal, Bank Secrecy Act fine, or money-laundering investigation, there is a compliance department that failed in its job. In the movies, compliance officers are usually the meek ones wearing glasses, hidden in windowless rooms at the end of long hallways. Compliance officers live in fear of missing something. “There are no great days, like, ‘Oh, my God, we just found that one of our portfolio managers was doing something wrong and we told it to the C.I.O. and we’re going to get him kicked out of here,’ ” Thomas Sporkin, a securities lawyer who represents compliance officers, said. “There’s no victory there.” When Mark Schein, a former Bronx prosecutor and enforcement lawyer for the New York Stock Exchange, became the chief compliance officer of the hedge fund York Capital Management, in 2005, he had golf shirts made. “On one side, it says ‘Your Capital Management Compliance Department,’ ” he said. “On the other side, it says ‘We Take the Fun Out of Funds.’ “ Despite compliance’s reputation as a buzzkill profession, its status rose during the Obama Administration. Regulations implemented after the financial crisis created a need for internal watchdogs, as did the concern raised by prosecutions of banks and hedge funds for mortgage fraud, currency-market rigging, and insider trading. In 2014, the Wall Street Journal went so far as to describe compliance as a potential “dream career.” But President Donald Trump, with his disregard for business-ethics standards, both in and out of office, is creating a new atmosphere. During cocktail hour by Camana Bay, holding plates of crab claws and sushi, conference-goers exchanged anecdotes about how traders at their firms were starting to ask whether the old, strict rules still applied. The compliance officers seemed to be channelling a concern about what leadership theorists call “tone at the top.” Michael Useem, a professor of management at Wharton, said that words alone don’t change rules, “but when repeated, promoted, articulated, in a whole variety of communication channels, it does affect the tone in the middle.” He went on, “The tone at the top right now coming from Washington may be sending a corrosive message on compliance, ethical behavior, and so on. I think it probably is, but we are going to have to wait and see.” (Useem did not attend the Grand Cayman conference, which is called GAIM Ops; I was there as a speaker.) Trump’s tone has been aggressive. In early February, he signed an executive order directing the Treasury Secretary to revisit Obama-era banking rules, and he has repeatedly complained about the burden of excessive regulation. (“Dodd-Frank is a disaster,” he declared, in January, referring to the financial-reform legislation that was passed after the 2008 crisis. “We’re going to be doing a big number on Dodd-Frank.”) His Administration has been hostile toward the Consumer Financial Protection Bureau, which was set up to protect consumers from the skullduggery of financial institutions, and, in March, he fired Preet Bharara, the U.S. Attorney for the Southern District of New York, who became famous for bringing insider-trading prosecutions. For the most part, Wall Street has been pleased by these signals. But Andrew Kandel, the chief compliance officer and co-general counsel at Cerberus Capital Management, a private-equity firm, said that regulation helps promote ethical behavior. He and Schein have given seminars at the Grand Cayman conference for seven years. “I try to scare people all the time by talking about the regulatory environment and how difficult it is, that the S.E.C. could examine us, or the C.F.T.C.,” he said, referring to the Commodities Futures Trading Commission. It’s one way to “remind people of how important it is to be compliant.” There are other ways as well, such as setting an example. “Making a lot of money any way you can is something that Trump brags about and advocates. And that creates a general climate. And you really need your people to be intimidated,” Schein told me. “When you have an atmosphere where people feel they can do whatever they want to make money, and regulation is going to be going away, it just makes our job a lot harder.”