Donald Trump often boasts on the presidential campaign trail that hardball tactics helped make him a successful businessman, an approach many voters say they admire. Those tactics have also left behind bitter tales among business owners who say he shortchanged them.

A review of court filings from jurisdictions in 33 states, along with interviews with business people, real-estate executives and others, shows a pattern over Mr. Trump’s 40-year career of his sometimes refusing to pay what some business owners said Trump companies...