Republican presidential candidate and reality television star Donald Trump has been deeply critical of former Secretary of State Hillary Clinton as he has embarked on his campaign, but it wasn’t always so.

The real estate magnate has a long history of delivering admiring comments about the woman he now calls the “worst Secretary of State in the history of the United States,” and a “desperate” and “sad” candidate.

When Clinton last ran for office, Trump was torn between supporting her and former New York City Mayor Rudy Giuliani. ” They’re both terrific people, and I hope they both get the nomination,” he told CNN in 2007, adding that he thought Clinton would surround herself with good people to negotiate a deal with Iran. A year later, Trump wondered publicly why Clinton wasn’t chosen as President Obama’s running-mate.

In 2012, as Obama was running for re-election, Trump called Clinton “terrific” again in an interview with Fox News, saying she performed well as Secretary of State.

“Hillary Clinton I think is a terrific woman,” he told Greta Van Susteren. “I am biased because I have known her for years. I live in New York. She lives in New York. I really like her and her husband both a lot. I think she really works hard. And I think, again, she’s given an agenda, it is not all of her, but I think she really works hard and I think she does a good job. I like her.

And on Fox and Friends on Wednesday, Trump explained why he donated to Clinton’s campaigns.

“I’m a businessman. I contribute to everybody,” Trump said. “When I needed Hillary, she was there. If I say ‘go to my wedding,’ they go to my wedding.”

Get our Politics Newsletter. The headlines out of Washington never seem to slow. Subscribe to The D.C. Brief to make sense of what matters most. Please enter a valid email address. Sign Up Now Check the box if you do not wish to receive promotional offers via email from TIME. You can unsubscribe at any time. By signing up you are agreeing to our Terms of Use and Privacy Policy . This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply. Thank you! For your security, we've sent a confirmation email to the address you entered. Click the link to confirm your subscription and begin receiving our newsletters. If you don't get the confirmation within 10 minutes, please check your spam folder.

Contact us at letters@time.com.