But in 2008, Trump thought Clinton should have been then-Sen. Barack Obama's vice presidential pick. It was even suggested multiple times on CNN during interviews Trump might have endorsed Obama instead of Arizona Sen. John McCain had Clinton been on the Democratic ticket.
Speaking with CNN that in 2008, Trump, asked if he might have endorsed Obama if she had picked Clinton said he was "a big fan" of her. Trump said she was "a terrific woman" and a "friend" and not picking Clinton hurt Obama "quite badly."
HOST: Let me ask you first about Barack Obama, is it true you would have thrown your support behind him. I was hearing possibly if he had would have picked Hillary Clinton you would have been right there with him.
TRUMP: I'm a big fan of Hillary. She's a terrific woman. She's a friend of mine. I think she was treated very poorly and I think it's hurt Barack Obama quite badly. She's a terrific woman.
Trump also told Wolf Blitzer "I don't understand why Hillary wasn't chosen" as Obama's VP pick. Trump added Obama "should have chosen Hillary."
TRUMP: Well, I can only say that Joe Biden got less than 1% of the vote every time he ran for president. I mean, you know, I don't understand why Hillary wasn't chosen because she was really winning. I have a friend that came to this country and was here for the last four weeks of that whole election. He said how did she lose? She won every election, she won every primary. He didn't understand it. The fact is that Obama went limping across the finish line. He should have chosen Hillary, it would have been a much different race, I believe. Right now, it looks to me like McCain is probably winning.
KING: Are you saying, though, that Biden would be better suited than Palin to step into that office?
TRUMP: No, I'm not saying that. I think she's made a tremendous impact. The impact that she has had on rejuvenating almost the Republican Party, it's been unbelievable. She has had a tremendous impact and frankly I didn't know who she was. Most people didn't know who she was. As soon as we got to see her and watch her, everybody's impressed. I think that really is to John McCain's credit. What he did in this choice is amazing because nobody else would have made it. It was a courageous choice. It has really reinvigorated the party.
KING: Have you formally endorsed the ticket?
TRUMP: No, but I'm endorsing McCain. I am basically very strongly -- you have to understand, I've known him, I like him, I respect him.
KING: So you're endorsing him?
TRUMP: He's a smart guy and I think he's going to be a great president.
KING: So you're endorsing him?
TRUMP: Sure, I'll endorse him on your show, why not?
KING: You just endorsed him.
TRUMP: I endorse him.
Asked if would have endorsed Clinton over McCain, Trump dodged saying "a great friend of mine. Her husband is a great friend of mine. They're fantastic people." He added of the Clintons "they are good people."
BLITZER: If Hillary Clinton had been the Democratic nominee, as opposed to Barack Obama, would you have endorsed her or John McCain?
TRUMP: Well, I would rather not say, because I don't have to worry about that.
But Hillary's a great friend of mine. Her husband is a great friend of mine. They're fantastic people. I mean, they're -- you know, the thing, they get a bad knock. She's a very nice woman. People think, tough, tough. And I guess she's 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, and all, but they are good people.
During the 2007 Democratic presidential primary, Donald Trump spoke favorably of Hillary Clinton, telling Wolf Blitzer that he thought she would win the nomination "rather easily."
"I know her very well," Trump said. "She's very talented. And she has a husband that I also like very much. I think she's going to get the nomination rather easily."
Trump also spoke favorably of Clinton's 2007 health care proposal that year which had at the center an "individual mandate" similar to the one President Obama would later include in his plan.
Trump's name is listed also on the Clinton Foundation's website as having donated between $100,000 and $250,000 and in the past has donated to Clinton's Senate campaigns.