In 2006, when a judge ordered Donald Trump's casino operation to hand over several years' worth of emails, the answer surprised him: The Trump Organization routinely erased emails and had no records from 1996 to 2001. The defendants in a case that Trump brought said this amounted to destruction of evidence, a charge never resolved.

At that time, a Trump IT director testified that until 2001, executives in Trump Tower relied on personal email accounts using dial-up Internet services, despite the fact that Trump had launched a high-speed Internet provider in 1998 and announced he would wire his whole building with it. Another said Trump had no routine process for preserving emails before 2005.

Judge Jeffrey Streitfeld was stunned. “He has a house up in Palm Beach County listed for $125 million, but he doesn’t keep emails. That’s a tough one,” he said, according to transcripts obtained by USA TODAY. “If somebody starts to put forth as a fact something that doesn’t make any sense to me and causes me to have a concern about their credibility in the discovery process, that's not a good direction to go, and I am really having a hard time with this.”