Trump takes umbrage at the idea that he went bankrupt, always pointing out that he never filed personally and that he used the bankruptcy laws to get richer.
Connolly said taking his casinos into Chapter 11 was "reasonable and responsible" and the right decision for Trump and his bondholders.
"It looked like a fair deal and actually kept them going," Connolly said.
But Mike D'Antonio, author of the book "Never Enough: Donald Trump and the Pursuit of Success," said the bankruptcies shouldn't come with bragging rights.
"Donald likes to say his bankruptcy filings were just a tool he's been using for his businesses," D'Antonio said. "He's had a string of failures. And you're not just talking about big investors. You're also taking about bond holders, not big banks...people who invested their retirements.
"So, you can call it a legal tool that he's using, but lots of people have been hurt along the way. It’s been a badge of shame for him."
Tom Winter is a New York-based correspondent covering crime, courts, terrorism and financial fraud on the East Coast for the NBC News Investigative Unit.