Jeff Ross Reveals The One Roast Joke Donald Trump Absolutely Can’t Stand

News & Entertainment Writer
07.22.16

Donald Trump accepted the Republican Party’s nomination on Thursday night, proving that what many thought was a joke candidacy announcement last summer is a bona fide bid for the White House. Throughout the entire process, however, one joke that has never changed is the one about all the times the Donald’s many business ventures have struggled through bankruptcy proceedings, or failed outright. A month after comedians Anthony Jeselnik and Lisa Lampanelli revealed just how much Trump hated such jabs, roastmaster Jeff Ross confirmed the nominee’s thin skin on Jimmy Kimmel Live.

“You could even make fun of his family and he doesn’t care,” Ross told Jimmy Kimmel. “What hurts him is if you make fun of the fact that he has gone bankrupt in the past. That’s the one thing that he’s super sensitive about. You can’t make fun of how much money he’s lost.”

When Kimmel pressed Ross for details, the comic told a behind-the-scenes story about Trump’s Comedy Central roast in 2011 that’s too good to be true (but probably is):

“The writers were sending him his jokes, and one of them said, ‘What’s the difference between a wet squirrel and Donald Trump?’ The punchline was, ‘A wet squirrel doesn’t have $2 billion.’ He wrote back, ‘Make it $10 billion.’ The writers wrote back, ‘How about $4 million?’ It became a business negotiation. They settled on $7 million. He didn’t care that they were making fun of his hair.”

Ross added that, should Trump actually become president and Kimmel steal the VP slot from Pence, there should be a new cabinet position for Roastmaster General: “He’s going to be like, ‘I need four insults about North Korea by three o’clock.”

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