WHEN YOU CAN'T EVEN BUY FRIENDS:

The old conundrum about whether it is better to be loved or feared has never posed much of a dilemma for Icahn. In "King Icahn," a 1993 biography, the author, Mark Stevens, described his subject as a "germophobic, detached, relatively loveless man," and quoted one contemporary saying, "Carl's dream in life is to have the only fire truck in town. Then when your house is in flames, he can hold you up for every penny you have." When the biography was published, Icahn stocked his office with copies to give to visitors. These days, he bristles at the term "corporate raider," favoring the euphemism "activist investor," but the reality is that when Icahn targets a company the response from management is generally terror. He has a volatile temper and a vindictive streak. [...]

 Icahn and Trump have known each other for decades, and Icahn supported his friend's aspirations for the White House at a time when they still looked quixotic. Trump has long boasted about his association with more successful businesspeople, dropping references to potentates the way kids decorate their school binders with the names of their favorite pop stars. But, in reality, many New York financiers considered him a buffoon. In 2015, Lloyd Blankfein, the C.E.O. of Goldman Sachs, greeted the suggestion that Trump might run for President by remarking that the notion of the former star of "The Apprentice" having his "finger on the button blows my mind." In this context, an endorsement from Icahn was a precious credential. On the campaign trail, Trump bragged about his "very dear friend Carl Icahn," the name functioning as a byword for boundless prosperity.

If Icahn was willing to be enlisted in this fashion, he was also prepared to drop Trump's name when it served his interest. Appearing on Bloomberg TV on August 16, 2016, he vowed that Trump would put an end to "these crazy regulations" on his first day in office. In fact, Icahn continued, he had spoken with Trump about the E.P.A. rule obliging his refiner to purchase renewable-fuel credits. If elected, Trump "will stop that," Icahn promised. "That's a hundred per cent."

Several weeks after Trump's victory, Icahn tweeted, "I've agreed to serve as a special advisor to the president on issues relating to regulatory reform." In a press release, Trump said, "Carl was with me from the beginning and with his being one of the world's great businessmen, that was something I truly appreciated. He is not only a brilliant negotiator, but also someone who is innately able to predict the future, especially having to do with finances and economies." He added that Icahn would help him address regulations that were "strangling" American business.

Icahn's role was novel. He would be an adviser with a formal title, but he would not receive a salary, and he would not be required to divest himself of any of his holdings, or to make any disclosures about potential conflicts of interest. "Carl Icahn will be advising the President in his individual capacity," Trump's transition team asserted.

In the months after the election, the stock price of CVR, Icahn's refiner, nearly doubled--a surge that is difficult to explain without acknowledging the appointment of the company's lead shareholder to a White House position. The rally meant a personal benefit for Icahn, at least on paper, of half a billion dollars. There was an expectation in the market--an expectation created, in part, by Icahn's own remarks--that, with Trump in the White House and Icahn playing consigliere, the rules were about to change, and not just at the E.P.A. Icahn's empire ranges across many economic sectors, from energy to pharmaceuticals to auto supplies to mining, and all of them are governed by the types of regulations about which he would now potentially be advising Trump.

Janet McCabe, who left the E.P.A. in January, and now works at the Environmental Law and Policy Center, told me, "I'm not naïve. People in business try to influence the government. But the job of the government is to serve the American people, not the specific business interests of the President's friends. To think that you have somebody with that kind of agenda bending the President's ear is troubling."

Conflicts of interest have been a defining trait of the Trump Administration. The President has not only refused to release his tax returns; he has declined to divest from his companies, instead putting them in a trust managed by his children. Questions have emerged about the ongoing business ties of his daughter and son-in-law, Ivanka Trump and Jared Kushner, who, since Trump took office, have reaped nearly two hundred million dollars from the Trump hotel in Washington, D.C., and from other investments. Although Trump promised to "drain the swamp," he has assembled a Cabinet of ultra-rich Americans, including two billionaires: Betsy DeVos, the Secretary of Education, and Wilbur Ross, the Secretary of Commerce.

But Icahn is worth more than the Trump family and all the members of the Cabinet combined--and, with no constraint on his license to counsel the President on regulations that might help his businesses, he was poised to become much richer. Robert Weissman, who runs the watchdog group Public Citizen, told me, "This kind of self-enrichment and influence over decision-making by an individual mogul who is simultaneously inside and outside the Administration is unprecedented. In terms of corruption, there's nothing like it. Maybe ever." In conversations with me, financiers who have worked with Icahn described his appointment as a kind of corporate raid on Washington. One said, "It's the cheapest takeover Carl's ever done."

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