One question we're often asked when talk turns to Trump's fortune: how can a man who has been bankrupt so many times remain a multi-billionaire? How is he worth more now, post-bankruptcies? We spoke to bankruptcy lawyers and casino industry experts - some of whom have had firsthand involvement in Chapter 11 cases connected to Trump - in an attempt to explain how he has survived corporate bankruptcies and thrived in the aftermath.įirst things first: Donald Trump has filed for corporate bankruptcy four times, in 1991, 1992, 20. Today, we value him at $2.7 billion, although he claims he's worth far more. Here at FORBES, we've been tracking Donald Trump's wealth since the inaugural Forbes 400 rich list in 1982.