On June 27, 1988, Mike Tyson and Michael Spinks stepped inside an Atlantic City boxing ring to spar for the title of world heavyweight champion. Billed as "Once and for All," the fight was hosted by Donald Trump, a then 42-year-old (and still only moderately famous) casino owner who paid $11 million for the privilege of splashing his name all over the high-profile showdown.
Less obviously to the public, that night also brought Trump into contact with a powerful investor named Carl Icahn. And while Tyson knocked out Spinks in 91 seconds, the relationship between the two businessmen went on to span decades. Crucially, as Trump's Taj Mahal casino was going bankrupt for the first time in 1991, the man he bonded with over boxing was there to help him weather the storm.
Now Icahn, an 81-year-old who made a fortune wresting control of the Taj, is already curating the new administration's policies. And the conflicts of interest are rampant: Most jarringly, Icahn is pushing to overhaul a major energy rule that cost his oil-refining business hundreds of millions of dollars last year. Out of the myriad ethical issues plaguing Trump's White House, from Kellyanne Conway shilling clothes on TV to the president constantly bringing the press to his own hotels, this one is uniquely galling because it could mean breaking a campaign pledge and sticking it to voters in a state he won last November.
If Trump is loathe to admit anyone might be a better capitalist than he it, he's come awful close to giving Icahn that honor. Despite Icahn once telling the Washington Post he "barely knew" Trump and arguing in court that the reality TV star was not trustworthy, the president has repeatedly referred to the man as his friend and as one of the world's greatest businessmen. Now that Trump is president, ethics watchdogs fear Icahn is all too willing to exploit what amounts to a one-sided love affair.
"[Icahn's] a little bit older, he's a little bit richer, he's also tall, which is very important to Trump," Jeff Hauser, executive director of the corruption watchdog group the Revolving Door Project, told me about their relationship. "It's not a mutual respect, but I think Icahn is definitely willing to sort of utilize the man crush that I think Trump has on him for his own advantage."
As the New York Times reports, Icahn helped Trump interview climate change denier Scott Pruitt before he was picked a Environmental Protection Agency (EPA) chairman, specifically asking about energy policy affecting his bottom line. He was also apparently involved with the appointment of Jay Clayton, whose firm has represented Goldman Sachs and other big banks, as chair of the Securities and Exchange Commission (SEC). And even if he weren't vetting personnel, Icahn being involved at all raised red flags given that he's a major fossil fuel and Wall Street player, and a company he owns a billion dollars of stock in is currently being investigated for alleged bribery in China.
But when Trump's transition team officially announced Icahn would serve as a special adviser on regulatory policies in December, it was careful to note he would not be a federal employee or a "special government employee"—distinctions that come with a bunch of legal and ethical restrictions. Semantics aside, the Times adds it didn't take long for Icahn to start trying to change what the paper dubbed an "obscure" EPA rule involving the gas Americans put in their cars every day.
The rule in question puts the onus on oil refineries to blend ethanol into gasoline. Trump once described himself as "100 percent" behind the ethanol mandate as part of his second-place caucus campaign in Iowa, where the biofuel is manufactured in large quantities from local corn. But Trump now has to balance the interests of Hawkeye State voters with those of his buddy. And Icahn is not exactly shy about it.
"Especially if I think he respects me, why the hell shouldn't I call him?" Icahn asked a Bloomberg reporter of his lobbying Trump on the issue, later adding, "And yeah, it helps me. I'm not apologizing for that."
Biofuel was originally pitched to America as something that might reduce national dependence on fossil fuels and decrease the carbon footprint, while critics argue it encourages deforestation and increases food costs. But if there's still (some) debate over whether or not biofuel is actually good for the environment in the long run, there's no question that Iowa's economy likes the stuff. Biofuels support more than 43,000 jobs there and account for about 3.5 percent of the state's GDP, according to the Iowa Renewable Fuels Association, an industry group.
The association's executive director, Monte Shaw, recognizes that fibbing to the people of Iowa about corn is a time-honored political tradition—and that the ethanol lobby has outsized power because Iowa enjoys special status in vetting presidential candidates. But even as Shaw concedes the new EPA director Icahn helped pick has the ability to tinker with renewable fuel standards, people in his industry are holding out hope that Trump will keep his word.
"President Trump has always said all the right things from the caucuses to the more recent public statements, but at the same time, he's appointed people who have said the opposite," he told me. "It makes you stay on your toes, but I don't see any reason to pull the fire alarm right now. I am making sure the extinguisher works."
Meanwhile, investors seem to believe the opposite: SEC filings from the oil refinery Icahn owns a majority stake in show that the ethanol rule cost the company, CVR Energy, $205 million last year. After Trump won, stock in CVR promptly skyrocketed.
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Democrats are understandably concerned about all of this. Seven US senators, including Elizabeth Warren and Sheldon Whitehouse, penned a letter to Icahn last week asking him to answer a list of questions, including whether he's been required to divest himself of any holdings and if he has an official government email address. Unfortunately for these would-be watchdogs, they probably can't compel Icahn to respond in a Republican-controlled Congress. The Democrats did CC Attorney General Jeff Sessions, but it's hard to imagine there will be any serious investigation unless and until the midterm elections shift the balance of power in Washington.
A better bet for getting to the bottom of this might be via an inspector general poking around internally or a regular person suing Icahn over the ethanol rule changes and compelling discovery. For now, the good-government group Common Cause is pushing the White House to classify Icahn as a special government employee so he has to adhere to budisclosure laws. But that's up to White House ethics counselor Stefan Passantino—the same guy who declined to discipline Kellyanne Conway for encouraging Americans to buy Ivanka Trump's clothes.
"The Trump White House claims that Carl Icahn isn't subject to federal conflict of interest laws applicable to executive branch employees," said David Vance, national media strategist at Common Cause. "The White House is wrong."
For his part, Hauser suspects that Icahn, who is 81, is making a risky but morbid gamble—that he's likely to die before any annoying oversight actually makes his life stressful, and that even if he were to get formally charged with some kind of ethics or legal violation, he'd be too old to experience real pain. After all, a 77-year-old former mentor to New Jersey governor Chris Christie was just sentenced to home confinement rather than a prison cell in a bribery case partially because he's a senior.
"This happened in the Sopranos, too," Hauser said. "We have a real problem in our society if we allow people who are old to do stuff while they are, like, functionally free of the possible sanction of jail."
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