The Most Explosive Moments In Donald Trump And Hillary Clinton's Bitter Feud

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There have been some signs that Hillary Clinton doesn't hate Trump as much as everyone thought, but then Hillary didn't hold back with her dark "daydream" about Trump during a November 2025 event either. The former secretary of state was co-hosting "History Has Its Eyes on Us" when the broadcast was interrupted by an emergency fire announcement, which Hillary admitted she hoped was a different kind of announcement, meaning one informing the public that the controversial president was no longer in office. "When a fire announcement interrupts the event... you might find yourself daydreaming about a 'Goodbye Trump,'" the author subsequently penned on X, formerly known as Twitter. 

There has been no love lost between the two politicians since they went head-to-head in the 2016 elections. From the get-go, Hillary ensured that there was no misperception of her relationship with Donald. The former secretary of state attended Donald and Melania Trump's wedding before their political feud but she made it clear during a subsequent interview with People that they are definitely "not friends," adding, "We knew each other, obviously, in New York. I knew a lot of people." Donald, for his part, gushed to Fox News in 2012 that Hillary was a "terrific woman" while reiterating that he was also quite fond of her husband, Former President Bill Clinton. 

The gloves came off as the two battled it out on the 2016 campaign trail, however, when he attempted to use Bill's past indiscretions to discredit his opponent. The former secretary of state, meanwhile, told People that it was just politics, and she wasn't taking it personally. But things got pretty personal as the campaign wore on, and to this day, the two remain locked in a bitter feud that has delivered its fair share of headline-making moments.

Donald Trump and Hillary Clinton's October 2016 showdown was labeled as the "ugliest debate in American history" by Politico. It's no secret that Trump has no filter, and Clinton doesn't take insults lying down. The two made it personal during that particular meeting, with the Republican asserting, "Believe me, she has tremendous hate in her heart." Trump also called his opponent the "devil." Clinton, for her part, grilled the former "Apprentice" host over those infamous "Access Hollywood" tapes, in which he pretty much confessed to sexually assaulting women. Trump ducked and dived, trying to divert attention away from him and back to Clinton's infamous email scandal. At one point, he claimed she wasn't fit to be president, proclaiming, "She's got bad judgment, honestly so bad that she should never be president of the United States." 

The former secretary of state clapped back, "I'm sorry I have to keep saying this, but he lives in an alternative reality." Then there was the memorable awkward question right at the end, which required both parties to tell the audience what they respected about each other. Trump was asked whether he would like to answer first, but he didn't respond, so Clinton stepped up. "Look, I respect his children," she confirmed, per CBS News. "His children are incredibly able and devoted, and I think that says a lot about Donald." 

Her Republican opponent, for his part, managed a compliment too: "I will say this about Hillary, she doesn't quit. She doesn't give up. I respect that. I tell it like it is. She's a fighter," (via YouTube). It was a sharp deviation from Trump's claim in the September 2016 debate that Clinton "doesn't have the stamina" to run the country, per CNN. 

Shortly after that brutal  October 2016 debate, Donald Trump and Hillary Clinton attended the annual Al Smith charity dinner, which presented them with a golden opportunity to properly roast each other. Naturally, neither party wasted any time in doing so. "Looking back, I've had to listen to Donald for three full debates, and he says I don't have any stamina," Clinton quipped, referencing the barb the divisive politician had made about her during their September meeting. "I have now stood next to Donald Trump longer than any of his campaign managers," she added (via CBSN). The former first lady also took jabs at his proposed Muslim ban, his renowned stinginess, and his unwillingness to release his medical records to the public. 

"Donald really is as healthy as a horse. You know, the one Vladimir Putin rides around on," Clinton said to loud laughs and some boos. Trump didn't hold back during his remarks either. "It's great to be here with a thousand wonderful people. Or as I call it, a small intimate dinner with some friends. Or as Hillary calls it, her largest crowd of the season," he snarked. The Republican also couldn't help bringing it back to the email scandal (again). "We have proven that we can actually be civil to each other," Trump started, referring to their messy debate. "In fact, just before taking the dais, Hillary accidentally bumped into me and she very civilly said, 'Pardon me.' And I very politely replied, 'Let me talk to you about that after I get into office.'" He took a shot at the media too, complaining that certain outlets were campaigning to get Clinton elected while smearing him. 

It had been over a year since she'd lost the 2016 presidential election, but Hillary Clinton was not done trading insults with former opponent Donald Trump. While celebrating the 25th anniversary of her husband, Former President Bill Clinton's, election at a forum in Little Rock, Arkansas, Hillary proudly claimed that she still lives rent-free in Trump's head. "Apparently, you know, my former opponent is obsessed with my speaking out," she bragged (via Politico). "Apparently there was another, somebody told me, tweet today. Honestly, between tweeting and golfing, how does he get anything done? I don't understand it. Maybe that's the whole point." The tweet Clinton was referring to did indeed indicate that she still gets under Trump's skin. 

The controversial politician wrote on X, "Crooked Hillary Clinton is the worst (and biggest) loser of all time" in response to what she said during a radio interview with 77 WABC. "Look, we have a man who's accused of sexual assault sitting in the Oval Office, don't we?" Clinton pointed out, calling the accusations against Trump "very credible," (via Today). The host seemed to balk at her frankness, asking, "How could you say that about President Trump?" Clinton casually responded, "Based on the very credible statements that have come forward from, I think now, a dozen women. And, really, based on his own words."

Fast forward to 2024, and Hillary Clinton and Donald Trump continued to butt heads. The former secretary of state released her new memoir, "Something Lost, Something Gained," in September, just as the divisive leader's campaign against Former Vice President Kamala Harris was heating up. The one-time presidential hopeful didn't mince words in the tome when it came to Trump either, offering her unvarnished thoughts on the January 6 Capitol insurrection alongside his unwillingness to accept that he'd lost the 2020 election. "Trump is not an aberration but an apotheosis... It reflected the Republican Party's strategy, starting in the 1960s, of embracing white supremacy in order to wield power," she penned. 

Meanwhile, Trump's second term in office saw the increasingly controversial politician openly using the Justice Department to seek retribution against his political adversaries, which obviously include Clinton. The president brazenly attempted to resuscitate his old lawsuit against his former opponent and Former FBI Director James Comey, in which he claims that they tried to smear his reputation by making false claims about Russian interference during the 2016 elections (the Senate Intelligence Committee found that there had been Russian interference and, moreover, Trump's camp hadn't exactly been against accepting the leg up). The case was previously thrown out in 2023, and the judge fined Trump and his lawyer, Alina Habba, for filing what he called a "frivolous" lawsuit, per NPR. 

Donald Trump proved he still had it in for Hillary Clinton when he decided to open an investigation into both her and her husband, Bill Clinton, in November 2025, based on their former association with convicted sex offender Jeffrey Epstein. It's worth noting that the president himself had a years-long friendship with the disgraced financier and is mentioned multiple times in the so-called Epstein files. Leading Democrat on the House Oversight Committee Robert Garcia professed that the president was launching the investigation into the Clintons to "deflect from serious new questions we have about his relationship with Jeffrey Epstein," per the BBC. House Committee on Oversight and Government Reform Chairman James Comer demanded that the Clintons sit down for a deposition with Congress in December 2025, warning that failing to adhere to their subpoenas would have dire consequences. 

"We expect to hear from Bill and Hillary Clinton," Comer confidently told "Just The News, No Noise," (via Newsweek). "Donald Trump answered questions for years about Jeffrey Epstein. Every day, he gets asked questions about Epstein, and he answers them in front of the American people." Comer also warned that the Clintons could face prison time if they failed to show up for their respective depositions.

Of course, there's no proof that either Hillary or Bill Clinton engaged in any illegal activity with Epstein. The same is also true of Trump. But like the president, the Clintons used to be tight with him. Hillary accepted money from Epstein to fund her Senate campaign in the 2000s, while Ghislaine Maxwell, Epstein's right-hand woman, notably attended Hillary and Bill's daughter, Chelsea Clinton's, wedding in 2010.