According to the Huffington Post, Trump reportedly made comments about Khloe Kardashian's weight when she was a contestant on 2009's Celebrity Apprentice. Three different sources at the show confirmed that Trump called her a "piglet" off camera and was looking for a reason to fire her. He also inferred that she was the "ugly" Kardashian.
On camera, he shamed her for a DUI.
Kardashian hasn't yet responded, but she was on Ellen recently.H/T Huffington Post