In the spring of 2016, Donald Trump’s incessant name-dropping of “fellow Queens-born billionaire” Carl Icahn on the stump motivated the Washington Post to publish a lengthy feature exploring their relationship:

These days, the tension has given way to apparent harmony. As Trump runs for president, he often fawns over the elite investor 11 years his senior, saying Icahn is one of “the great businessmen of the world” and sharp enough to master U.S. negotiations with China or run the Treasury Department. Icahn has endorsed Trump, saying the country would be “lucky” to have him in the Oval Office.

When the Grab ‘Em By the Pussy tape came out in October, Ichan stood by his man.

“Over my years I’ve listened to a lot of salacious talk in locker rooms, bachelor parties, et cetera, by a lot of high-level people, some of whom are now supposedly so outraged,” Icahn told CNBC.com in a phone interview. “All I can do is refer to that great quote, ‘Let he who has not sinned cast the first stone.’”

And he was rewarded, although not with a position as Treasury Secretary. Trump made him “a special advisor to the president on regulatory reform,” but to avoid scrutiny he wasn’t hired as a federal employee. In that roll, Icahn vetted candidates to lead the Environmental Protection Agency and Securities and Exchange Commission. His conflicts of interest were so glaring and the criticism so relentless, that he submitted his resignation in August 2017, having served less than seven months in the position.

Billionaire investor Carl Icahn ended his role as a special adviser to U.S. President Donald Trump on Friday after facing criticism that policy recommendations he offered could help his own investments.

Some Democratic lawmakers and biofuels advocates argued that Icahn’s guidance to the Republican administration created a conflict of interest with his businesses, including oil refining company CVR Energy Inc.

This may be the only example of anyone resigning from Trump’s administration over a conflict of interest. But Icahn had bigger problems. In 2023, Hindenburg Research released a damaging examination of his market cap holding company, Icahn Enterprises (IEP). They discovered that Icahn’s investment portfolio had lost 53 percent of its value since 2014, compared to a 147 percent gain for the S&P 500. A deeper dive revealed other troubling facts, including that, by a wide margin, it traded at the highest premium relative to net asset value of any of the “526 U.S. based closed end funds (CEFs) in Bloomberg’s database.” And they publicized that Icahn had “pledged 181 million units, worth over $9 billion, to secure his own “personal indebtedness,” which put investors at “potential risk of a margin call and forced asset sale should IEP units eventually trade around or at a discount to NAV, like virtually all of its peers.”

In truth, Icahn only belatedly admitted that he had secured billions of dollars of personal margin loans by pledging outstanding stock in IEP. And that failure to report turned out to be criminal fraud.

The U.S. Securities and Exchange Commission announced Monday that it settled charges against billionaire activist investor Carl Icahn and his publicly traded company Icahn Enterprises L.P. IEP after regulators alleged that he failed to disclose billions worth of personal loans pledged against Icahn Enterprises’ securities.

The problem for Icahn is that Jay Clayton, the man he had approved to head the SEC, and who subsequently brought the fewest insider trading cases since the Reagan administration, is no longer on the job. He was replaced in the Biden administration by Gary Gensler. So, this happened:

Washington D.C., Aug. 19, 2024 —
The Securities and Exchange Commission today announced charges against Carl C. Icahn and his publicly traded company, Icahn Enterprises L.P. (IEP), for failing to disclose information relating to Icahn’s pledges of IEP securities as collateral to secure personal margin loans worth billions of dollars under agreements with various lenders. IEP and Icahn agreed to pay $1.5 million and $500,000 in civil penalties, respectively, to settle the SEC’s charges.

This may be couch change to Icahn, but on the other hand, he sounds kinda broke. IEP is trading 76 percent below its 2019 level, and 23 percent below its price one year ago. And he’s been breaking the law to secure his own personal finances.

He doesn’t seem, as Trump claimed, to be one of “the great businessmen of the world.” He seems like another “Queens-born billionaire” who has built a house of cards based on an unearned reputation.

He and Trump are birds of a feather, and their comeuppance is overdue.

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