Donald Trump didn't always think of Hillary Clinton as a "nasty woman". In fact, he used to be a big fan.

A newly discovered tape, from an interview that aired days after the 2008 presidential election, shows Trump showering his current nemesis with praise.

Clinton was reeling at the time, having lost the Democratic nomination to Barack Obama in a bruising contest months earlier. Her ambitions were in tatters, but Trump still thought she had a bright future in politics.

Democratic presidential nominee Hillary Clinton. Photo / AP
Democratic presidential nominee Hillary Clinton. Photo / AP

"I think her history is far from being over. I'd like to answer that question in another 15 years from now. She's going to go down, at a minimum, as a great senator," Trump told NY1 News.

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"I thought (the Obama campaign) roughed her up pretty good. I think she's a wonderful woman, I think that she's a little bit misunderstood. You know, Hillary's a very smart woman, a very tough woman, that's fine. But she's also a very nice person.

"I know Hillary, and I know her husband very well, and they're fine people. But I thought she was perhaps unnecessarily roughed up. She took some pretty hard hits."

Wonderful. Smart. Misunderstood. Nice. Those compliments are jarring, considering how relentlessly critical Trump is of Clinton these days. He called her a "nasty woman" to her face at the last presidential debate, and for months he's claimed she deserves to be in jail.

But that wasn't the only time he'd publicly complimented Clinton. Before he ran for president against her, Trump clearly liked her.

"I know her very well, and I know her husband very well, and I like them both. They are just really terrific people, I like them both very much," he told NBC News in 2013, for example.


"I think you'll be looking at the record of Hillary Clinton, and how did she do as secretary of state - probably above and beyond everybody else."

"I know her, and she'd make a good president or a good vice president," he said on radio in 2008.

"Hillary's a great friend of mine, her husband is a great friend of mine, they're fantastic people," he told CNN the same year. "They get a bad knock. She's a very nice woman. People think tough, tough, and I guess she is tough, but she's a very nice woman and he's a very nice guy. We know all about the smarts and how smart they are, but they are good people."

Trump actually donated to the Clintons on several occasions. Hillary Clinton took his cash in 2002, 2005, 2006 and 2007, when she was running for president the first time. He also gave the Clinton Foundation $100,000, Politico reports.

Oh, and the Clintons attended his wedding to his third and current wife, Melania.

That web of connections between Trump and the Democratic nominee were brought up incessantly by Trump's opponents in the Republican primaries. The party's voters picked him anyway - but that doesn't make the situation any less awkward now.