Trump and his team of attorneys have promised to challenge Judge Engoron's decision, but their past legal efforts have often been rejected by state and federal courts.
"What we've seen with Donald Trump over and over again is that often arguments that gain traction with his supporters are flatly inconsistent with the law," said Thomas of the University of Michigan.
One of Trump's claims has been that he played by the same rough-and-tumble, buyer-beware accounting rules that shape much of New York City's real estate industry.
"Most of the time that's just not going to be much of a winner of an argument," said Thomas. "Telling a police officer, 'I know I was speeding but so was everyone else' — that doesn't get you off the hook."
In his ruling, Engoron blasted Trump's legal arguments as "absurd."