30 times Stephen Colbert embarrassed Donald Trump

Photo: CBS
Photo: CBS /
6 of 30

25. Trump says a million dollars is no big deal

Donald Trump was born richer than most of us can ever hope to be, but you wouldn’t know that by talking to him. Trump insists that he has always been an “underdog” fighting from the very bottom to get to where he is today. The problem with that is it’s clearly not true.

On The Late Show, Stephen Colbert played a clip of Donald Trump talking about starting his own business in Manhattan, brushing past the fact that his father gave him “a small loan” of one million dollars. The late night host found it so hilarious Trump considered such a high sum of money to be no big deal, and encouraged Trump to prove that point.

Colbert unveiled a giant check on the show, with a million dollars addressed to the charity of the Harlem Children’s Zone courtesy of Trump. All Trump would need to do is sign the check, which would truly show that this amount is no big deal to give away:

“Now Mr. Trump, all you have to do is come here and sign it, proving that a million dollars is a small amount of money. Especially when it’s helping other people get a start in Manhattan. Who knows, the kids you help might one day be so rich, they can blow their cash on a presidential campaign.”

Next: 24. Trump is a bully