Anthony Jeselnik
Ben Cohen—NBC/Getty Images
By Daniel White
September 17, 2015

As a presidential candidate, Donald Trump has not taken kindly to people who question his business acumen and his fortune. At Wednesday’s Republican debate, he took offense when former Hewlett Packard CEO Carly Fiorina attacked his business record.

“You ran up mountains of debt, as well as losses, using other people’s money, and you were forced to file for bankruptcy,” Fiorina said. “I never filed for bankruptcy” Trump shot back. (They’re both right. Although Trump’s casinos have restructured in bankruptcy court, he has never filed for personal bankruptcy.)

As it turns out, this may be Trump’s Achilles heel. In an interview with the Broward-Palm Beach New Times last year, comedian Anthony Jeselnik revealed Trump has long been sensitive about his wealth. Jeselnik said that comedians at the 2011 Comedy Central roast of Trump were barred from joking that The Donald has less money than he says.

Roastees typically are allowed to bar jokes on sensitive topics, but the choice was unusual. In a 2012 interview with WatchMojo.com, Jeselnik said Charlie Sheen said roasters had to avoid bringing up his mother, while Mike Tyson said his rape conviction was off limits. Trump, meantime, was willing to take barbs about his spouse and his treatment of black tenants, but he didn’t want to be criticized over his bank account.

The Trump campaign did not respond to a request for commment.

For Republicans who have been debating how to handle the current frontrunner, Jeselnik’s advice seems pretty revealing. Still, he said that he found it hard to pin Trump down, noting that he’s “super rich, and it doesn’t seem like he could be hurt.”

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