They Loved Him Until He Ran

Ten Well-Known People Who Praised Donald Trump, Then Turned Against Him

For more than thirty years before he ever ran for president, Donald Trump was welcome almost everywhere. He was on the talk shows. He was at the charity dinners. Politicians from both parties took his checks and came to his parties, and when he got married in 2005, a sitting United States senator sat in the front pew. He was a builder, a television star, and a name that sold books and buildings. People liked being seen with him. Then on June 16, 2015, he rode the escalator down into the atrium of Trump Tower in New York and announced he was running for president as a Republican. And almost overnight, many of the same people who had praised him, laughed with him, and shaken his hand for decades decided he was the most dangerous man in America.

How does that happen? Did the man change, or did something else change?

I don't want you to take my word for how much these people once admired him. I want you to hear it from them.

So here are ten of them. Each one is a well-known public figure, and every quote below is their own words, dated, and sourced at the end of this article. I have held every one of them to the same standard regardless of which party they belong to. Where the record is thin, I say so. Where the praise came after he announced, I say that too.

1. Hillary Clinton

In January 2005, Hillary Clinton was a senator from New York, and she sat in the front pew at Donald Trump's wedding to Melania in Palm Beach. Years later, in January 2016, she was asked about that friendship at a Democratic forum in Des Moines, and she explained it this way: "He was basically a Democrat before he was a Republican." She said he had been supportive of Democrats, and that now he seemed to have taken another road. Five months after that, on June 2, 2016, she stood in San Diego and told the country, "Donald Trump's ideas aren't just different; they are dangerously incoherent." In the same speech she called him "temperamentally unfit to hold an office that requires knowledge, stability and immense responsibility."

The wedding guest became the opponent. Same man.

2. Bill Clinton

Bill Clinton came to the wedding reception at Mar-a-Lago. And according to a 2015 Washington Post report, confirmed by Clinton's own office, the two men talked on the phone in May 2015, only a few weeks before Trump announced. The Post reported that Clinton encouraged him to take a larger role in the Republican Party and told him he was striking a chord with frustrated conservatives. Clinton's office said the 2016 race was never discussed. Either way, it was a friendly call. Sixteen months later, in September 2016, Bill Clinton was campaigning for his wife in Orlando, Florida, and suggesting that Trump's "Make America Great Again" slogan carried a racial message. "If you're a white Southerner, you know exactly what it means, don't you?"

3. Chuck Schumer

Chuck Schumer's relationship with Trump goes back a long way. Their families were both in the building business in Brooklyn, and Federal Election Commission filings show Trump gave Schumer $8,900 between 1996 and 2009. In 2006, Schumer appeared on The Apprentice and said of him, "Even when [Trump] was much younger, you knew that he was going to go places." And he did go places. He went all the way to the White House. In February 2017, three weeks after the inauguration, Schumer told TIME, "Right now, it looks like I'm going to be spending more time opposed." He said Trump was moving to the hard right on issue after issue.

4. Jesse Jackson

In 1999, Jesse Jackson's Rainbow/PUSH Coalition held a Wall Street Project event in New York, and Donald Trump was there. Trump had given the project office space at 40 Wall Street. Jackson thanked him publicly that night and praised his commitment to diversity on Wall Street: "Beyond that, in terms of being inclusive, he's done that too." I want to be honest about this one. The 1999 quotes have been widely repeated, but I have not been able to find the original video or transcript, so I am relying on secondhand reports. The later quote is solid. At the Ministers March for Justice in Washington, D.C., in 2017, Jackson said, "Jesus would not qualify to come in Trump's country," and that Trump "would not qualify to get into Jesus' kingdom."

From inclusive to unworthy of heaven. That is quite a distance for one man to travel in eighteen years, and I don't believe Trump was the one who traveled it.

5. Oprah Winfrey

In 1988, Donald Trump sat on Oprah Winfrey's couch, and she could hardly get over the response he got from her audience. "People stood up and roared and cheered when you walked in," she told him. "Why is that? What is this fascination?" She even asked him whether he would ever run for president. Now, Oprah never endorsed him, and I don't want to claim more than the tape shows. But the tape does show what America thought of him then. Thirty-six years later, on November 4, 2024, the night before the election, Oprah stood on the steps of the Philadelphia Museum of Art at a rally for his opponent and warned, "If we don't show up tomorrow, it is entirely possible that we will not have the opportunity to ever cast a ballot again."

6. Howard Stern

Few people in media spent more hours with Donald Trump than Howard Stern. From the early 1990s until 2015, Trump was one of his most frequent guests, and the two men attended each other's weddings. Stern once said Trump was as unguarded as any human being who had ever been on his show. Then in September 2024, Stern said on the air that Trump should not be anywhere near the White House, and he went further than that. He turned on the voters. "I hate the people who vote for him. I think they are stupid."

Think about what that means. For twenty years he invited the man into his studio as a friend, and now he says he has no respect for the tens of millions of Americans who agree with him. If you want to understand where that kind of feeling comes from, I wrote about it in The Problem of Hatred.

7. Mitt Romney

This one will mean more to many of my readers than any other on the list. On February 2, 2012, at Trump's hotel in Las Vegas, Mitt Romney accepted Donald Trump's endorsement for president. "I'm so honored to have his endorsement," Romney said. "There are some things that you just can't imagine in your life. This is one of them." Four years later, on March 3, 2016, Romney stood at the Hinckley Institute of Politics at the University of Utah and said, "Donald Trump is a phony, a fraud."

He was honored to stand next to him in 2012. By 2016 the same man was a fraud. What happened in between? Trump ran.

8. Whoopi Goldberg

I need to be fair here. Whoopi Goldberg was never a big admirer of Trump's politics. In 2011 she challenged him to his face on The View about his claims concerning President Obama's birth certificate. But she called him a friend, and she meant it. On October 12, 2015, four months after he announced, she told her audience, "He's a friend, I like him as a person. I don't want him representing me." That is about as honest a statement as anyone made in 2015. She liked the man. She did not want him in power. By October 2024 she was saying, "I have not been a fan."

9. Mark Cuban

Mark Cuban's praise came after the announcement, not before, but it was strong praise. In July 2015, a few weeks after Trump came down that escalator, Cuban called his candidacy "probably the best thing to happen to politics in a long, long time." He liked that Trump gave honest answers instead of prepared answers. One year later, on July 30, 2016, Cuban stood at a Hillary Clinton rally in Pittsburgh and endorsed her. "Initially, I really hoped he would be something different," he said. By September he was telling CNNMoney that Trump was "an immediate and present danger."

10. Lindsey Graham

Trump gave Senator Lindsey Graham's campaign $2,600 in 2014. In July 2015, after Trump had announced and the two were rivals for the nomination, Graham was asked whether he would give the money back. He said he would keep it, and he still had something good to say: "He's done a lot of good for the wounded warrior program." By February 2016 that was gone. "I think he's a kook. I think he's crazy. I think he's unfit for office." Graham is the one name on this list who later came all the way back around and became one of President Trump's strongest allies in the Senate. I include him anyway, because for a season he followed the same pattern as everyone else.

What Changed?

Go back through that list and ask yourself what Donald Trump did between the wedding and the escalator that turned a senator, a former president, a civil rights leader, a talk show host, a radio host, and a presidential nominee against him. Did he change his personality? No. He was the same loud, blunt, brash New York builder in 2015 that he was in 1988 on Oprah's couch. Did he change his manners? No. Howard Stern knew exactly how he talked. He had twenty years of tape. The one thing that changed was that Donald Trump stopped being a celebrity and started being a threat to power. He was no longer someone you invited to your party. He was someone who might take the party away from you.

I don't say this to condemn any of these ten people. They are entitled to their opinions, and some of them, like Whoopi Goldberg, were honest enough to separate the man from the politics. But I do want you to see the pattern. Because none of this is new.

It was written down twenty-seven hundred years ago.

Isaiah Saw It Coming

Isaiah saw a servant of God who would rise to great heights before his image was destroyed in the eyes of the world...

Behold, my servant shall deal prudently, he shall be exalted and extolled, and be very high. As many were astonied at thee; his visage was so marred more than any man, and his form more than the sons of men: (Isaiah 52:13–14)

Look at the order Isaiah gives. First, this servant deals prudently. The Hebrew word relates to wisdom, skill, and success in one's dealings, and Donald Trump wrote The Art of the Deal. His whole public identity before politics was built on his reputation as a dealmaker. Second, he shall be exalted and extolled, and be very high. Before his image was marred, Trump was one of the most famous people on earth. He hosted a hit television show for fourteen seasons. His name was on buildings, casinos, and golf courses around the world. That is the man Oprah's audience stood up and cheered for. That is the man Chuck Schumer said was going places, the man Hillary Clinton sat in the front pew for, the man Mitt Romney was honored to stand beside. Third, his visage is marred more than any man. His visage is his public face, his image and his reputation. The man who was once admired, celebrated, and sought after by the powerful becomes the most vilified figure on earth.

You just read ten examples of it, in their own words.

I believe Isaiah was describing Donald Trump, and I explain why in what scripture actually says about Trump and prophecy. It is the same pattern I describe in the marred servant and why a destroyed reputation is part of the prophecy. The marring did not come from what he did. It came from what he was about to do. And Isaiah also wrote about how that story ends for those who were incensed against him.

I have watched this same thing happen on a much smaller scale with people I know. Friends who never said a word about Trump for decades suddenly could not hear his name without anger, and a few of them could not hear mine either. If you have felt that anger yourself, I would ask you to stop and look at where it came from. Was it something he did? Or was it something you were told? I wrote about that in what you believe colors everything you see. The people on this list knew him better than most of us ever will. They praised him with their own mouths. Then he ran, and so did they, in the other direction.

I believe there is more to this story than politics. I believe it was prophesied. And I believe we are going to watch the rest of it unfold, just as Isaiah saw it.

In the name of Jesus Christ, amen.

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Keep Reading

• The Four Horsemen of the Apocalypse: What Each One Actually Represents
• They Are Not Fighting Me. They Are Fighting Him.
• If Opposition Is the Measure, Trump Is the Greatest Leader in History

The First Horseman, Donald Trump and Biblical Prophecy is available in print, digital, and audiobook at FirstHorseman.World.

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Sources

Trump's announcement, June 16, 2015

• The American Presidency Project, UC Santa Barbara: https://www.presidency.ucsb.edu/node/314769

Isaiah 52:13–14

• https://www.churchofjesuschrist.org/study/scriptures/ot/isa/52?lang=eng

1. Hillary Clinton

• Wedding attendance, January 22, 2005 (PolitiFact): https://www.politifact.com/factchecks/2015/jul/21/carlos-curbelo/clintons-really-did-attend-donald-trumps-2005-wedd/
• "Basically a Democrat," January 11, 2016, Brown & Black Democratic Forum, Des Moines (ABC News): https://abcnews.com/Politics/hillary-clinton-donald-trump-wedding/story?id=36228477
• San Diego speech, June 2, 2016 (CBS News): https://www.cbsnews.com/news/clinton-bashes-trumps-dangerously-incoherent-foreign-policy/

2. Bill Clinton

• May 2015 phone call, as reported by The Washington Post, August 5, 2015 (The Fiscal Times summary): https://www.thefiscaltimes.com/2015/08/05/Donald-Trump-s-Curious-Clinton-Connection
• Orlando remarks, September 2016 (Fox News): https://www.foxnews.com/politics/bill-clinton-suggests-trump-slogan-racist-but-he-used-the-same-one.print

3. Chuck Schumer

• The Apprentice, Season 5, 2006 (Fox News): https://noticias.foxnews.com/politics/schumers-apprentice-praise-trump-goes-viral-going-go-places
• Trump donations to Schumer, 1996–2009, from FEC filings (Washington Free Beacon, November 17, 2016): https://freebeacon.com/?p=689896
• TIME interview, February 9, 2017: https://time.com/4664849/donald-trump-chuck-schumer-interview/

4. Jesse Jackson

• 1999 Wall Street Project remarks (secondhand, BizPac Review): https://www.bizpacreview.com/2016/09/02/remember-jesse-jackson-praised-trump-commitment-diversity-yeah-neither-385142/
• 2017 Ministers March for Justice (Dayton Daily News): https://daytondailynews.com/rare-politics/jesse-jackson-president-trump-would-not-qualify-to-get-into-heaven

5. Oprah Winfrey

• 1988 interview (Fox News): https://noticias.foxnews.com/politics/flashback-oprah-winfrey-called-trump-a-folk-hero-during-interview-said-he-was-more-popular-than-a-listers.print
• Snopes on whether Oprah endorsed Trump: https://www.snopes.com/oprah-endorsed-donald-trump-false/
• Philadelphia rally, November 4, 2024 (Fox News): https://www.foxnews.com/politics/final-harris-rally-oprah-warns-trump-presidency-could-end-voting-rights.print

6. Howard Stern

• The Stern and Trump history (Rolling Stone): https://www.rollingstone.com/culture/culture-news/howard-stern-donald-trump-president-interview-833343/
• September 2024 remarks (Daily Wire): https://www.dailywire.com/news/howard-stern-says-he-doesnt-hate-trump-but-the-people-who-vote-for-him

7. Mitt Romney

• Endorsement, February 2, 2012, Las Vegas (ABC News): https://abcnews.com/blogs/politics/2012/02/trump-backs-romney-says-he-wont-let-bad-things-happen
• Hinckley Institute speech, March 3, 2016 (Foreign Policy): https://foreignpolicy.com/2016/03/03/romney-trumps-imagination-must-not-be-married-to-real-power/

8. Whoopi Goldberg

• The View, October 12, 2015 (TheWrap): https://www.thewrap.com/whoopi-goldberg-donald-trump-friend-global-negotiator-korea/
• October 28, 2024 remarks (Denver Gazette): https://www.denvergazette.com/?p=402963

9. Mark Cuban

• July 2015 Cyber Dust post (CNBC): https://www.cnbc.com/2015/07/28/mark-cuban-says-donald-trump-has-changed-the-game-of-politics.html
• Pittsburgh rally, July 30, 2016 (NBC News): https://www.nbcnews.com/politics/2016-election/billionaire-mark-cuban-endorses-hillary-clinton-rips-trump-n620406
• CNNMoney interview, September 2016: https://money.cnn.com/2016/09/21/media/mark-cuban-donald-trump/index.html

10. Lindsey Graham

• July 2015, keeping Trump's donation (NBC News): https://www.nbcnews.com/politics/2016-election/lindsey-graham-im-keeping-trumps-campaign-donation-n388961
• February 2016 Fox News remarks (Salon): https://www.salon.com/2017/11/30/lindsey-graham-should-learn-something-from-lindsey-graham/

Photo Credits

• Official portraits of Donald Trump (White House photo by Shealah Craighead, 2017), Hillary Clinton, Bill Clinton, Chuck Schumer, Mitt Romney, and Lindsey Graham: U.S. government works, public domain.
• Howard Stern: photo by Bill Norton, May 10, 2012, licensed under CC BY 2.0 (https://creativecommons.org/licenses/by/2.0/). Cropped.
• Mark Cuban: photo by Gage Skidmore, 2019, licensed under CC BY-SA 3.0. Resized from the supplied crop.
• Whoopi Goldberg: photo by Shawn Miller, Library of Congress, May 10, 2024, CC0.
• Oprah Winfrey: Official White House photo by Lawrence Jackson, November 20, 2013, Presidential Medal of Freedom ceremony. Public domain. Resized.
• Jesse Jackson: Photo by Warren K. Leffler, July 1, 1983; digital retouching by Chick Bowen. Library of Congress, public domain. Resized.