Trump bought a $10 million Super Bowl ad when he didn’t yet have a challenger. He tapped his political organization to cover exorbitant legal fees related to his impeachment. Aides made flashy displays of their newfound wealth — including a fleet of luxury vehicles purchased by Brad Parscale, his former campaign manager.

Meanwhile, a web of limited liability companies hid more than $310 million in spending from disclosure, records show.

Now, just two weeks out from the election, some campaign aides privately acknowledge they are facing difficult spending decisions at a time when Democratic nominee Joe Biden has flooded the airwaves with advertising. That has put Trump in the position of needing to do more of his signature rallies as a substitute during the coronavirus pandemic while relying on an unproven theory that he can turn out supporters who are infrequent voters at historic levels.

“They spent their money on unnecessary overhead, lifestyles-of-the-rich-and-famous activity by the campaign staff and vanity ads way too early,” said Mike Murphy, a veteran Republican consultant who advised John McCain and Jeb Bush and is an outspoken Trump critic. “You could literally have 10 monkeys with flamethrowers go after the money, and they wouldn’t have burned through it as stupidly.”