In doing so, Trump missed an opportunity to take some of the heat off his campaign as it struggles through the final weeks of the race.
He opened with some more light-hearted remarks, referencing his "beautiful hands" and joking about how his crowds at rallies dwarf Clinton's.
"It's great to be here with 1,000 wonderful people. Or, as I call it, a small, intimate dinner with some friends. Or as Hillary calls it, her largest crowd of the season," Trump said, to which Clinton laughed.
But the mood turned dour when Trump began to directly take on Clinton.