The true reason behind Trump’s 19-year feud with Rosie O’Donnell

Inside Hollywood’s longest celebrity grudge

For nearly two decades, Donald Trump and Rosie O’Donnell have been locked in one of the most bitter celebrity feuds in modern pop culture. What started as a sharp exchange on live TV spiraled into a personal and political battle that refuses to die down, even in 2025.

From public insults to legal threats, this feud has crossed lines most never imagined. Curious what really sparked it and why it’s still going strong?

How it all began (2006)

In December 2006, Rosie O’Donnell mocked Donald Trump on The View by imitating his signature hair flip and calling him a “snake‑oil salesman.” She also criticized his handling of Miss USA Tara Conner’s scandal, questioning his moral authority due to his bankruptcies and divorces.

Trump responded by calling Rosie a “woman out of control” and a “loser,” even threatening to sue her in People magazine. That sharp exchange marked the start of a long‑running personal rivalry that resurfaced time and again.

Trump’s media blitz

By early 2007, Trump had launched a full media campaign, appearing in interviews and issuing public insults toward Rosie. He accused her of making false statements and vowed to “take lots of money” from her, a reference to a possible lawsuit that never materialized.

This media offensive intensified Rosie’s discomfort and contributed to her decision to quit The View in April 2007. The clash highlighted how both used media platforms to amplify their feud.

Momentary pause (2007)

After Rosie left The View, there was a brief lull in their feud. Interestingly, Trump briefly sided with Rosie when she criticized the Iraq War, calling her stance valid but still slinging mild insults.

The break didn’t mend fences, but it showed subtle complexities beneath the hostility. That moment illustrated that their feud wasn’t purely personal, it also involved political and moral disagreements.

Engagement drama (2011)

In December 2011, Rosie announced her engagement to Michelle Rounds, and Trump didn’t congratulate her. Instead, he mocked her engagement on Twitter, expressing pity for Rounds’ parents and again calling Rosie a “loser.”

Rosie fired back on social media, calling Trump an “ass” and further escalating the feud. Their public squabble drew new attention to the personal animosity that never faded.

Targeting Cher (2012)

In May 2012, Trump combined criticism of both Cher and Rosie in a single tweet, calling them “total losers.” Rosie had no involvement in Cher’s political commentary, yet Trump lumped their names together.

Rosie later suffered a heart attack in August, and Trump’s tweet wishing her well was oddly compassionate. This cycle of insult followed by rare concern illustrated their volatile back‑and‑forth.

Heart attack & cooldown

Rosie’s near‑fatal heart attack in August 2012 suspended hostilities briefly. Trump tweeted a get‑well message, saying, “I’m starting to miss you,” which surprised Rosie.

She joked on social media, asking if Trump was “trying to kill me.” While kind‑sounding, Trump’s gesture did little to ease the underlying tension that had been brewing for years.

Weight‑Loss Surgery Attack (2014)

Rosie underwent weight‑loss surgery in 2014 and spoke openly about body‑image struggles. Trump mocked her again, calling her confession “not politically correct” and digging into her surgery.

Rosie snapped back simply with “Donald — go away.” Their feud resumed, this time with Trump attacking her personal health choices, hitting a new low.

Return to The View (2014)

By July 2014, Rosie rejoined The View, and Trump wasted no time insulting her on Twitter. He labeled Rosie “crude, rude, obnoxious, and dumb,” though he claimed he still “liked her very much.”

The attack showed how he used her public appearances to fuel their feud. Rosie, however, stayed silent on that one, choosing to focus on her show rather than engage.

Bullying admitted by Rosie

In September 2014, Rosie described the feud as the worst bullying she’d ever experienced, even worse than childhood events. The nationwide attention made the feud feel much larger and harmful to her well‑being.

She publicly reflected on the emotional toll, emphasizing the intensity of Trump’s words. At that point, the dispute had become toxic for both sides.

Rosie quits again (2015)

Rosie left The View for a second time in early 2015, citing stress, much of which stemmed from her feud with Trump. Trump responded gleefully, calling her a “trainwreck” and reiterating, “Rosie is a loser.”

That exchange reaffirmed how their stoush remained central in their public images. Both leveraged the other as a foil in the media.

2015 debate shock

During an August 2015 Republican debate, when Megyn Kelly asked about derogatory comments toward women, Trump laughed and said, “Only Rosie O’Donnell.” The audience erupted in laughter as he deflected criticism by referencing his feud.

This moment publicly elevated Rosie’s name in the conservative arena. It revealed how Trump used personal attacks to manage political criticism.

2016 campaign references

In September 2016, Trump again said harsh things about women were only directed at Rosie. He claimed, “Rosie O’Donnell … deserves it,” twisting his attacks as justified.

Rosie responded by posting a scathing and defaming remark, calling him “an orange anus.” The back‑and‑forth intensified their feud during a high‑stakes election year.

Rosie’s mental health

Rosie revealed that Trump’s attacks deeply affected her mental health during his presidency. In 2017 interviews, she admitted to struggling emotionally, describing the bullying as overwhelming.

She worried about surviving under his rule, comparing the presidency to a personal trauma. This emotional response showed how the feud went beyond jokes; it harmed real lives.

Living through presidency

In October 2017, Rosie shared she didn’t know if she could live through Trump’s term. She worried about the country’s future and described her own anxiety during the presidency.

She even appeared at a White House protest in August 2018. Her activism demonstrated how the feud had turned into a broader political stance.

Threat to strip citizenship (July 2025)

On July 12, 2025, Trump said on Truth Social he might revoke Rosie’s U.S. citizenship, calling her a “threat to humanity” and urging her to remain in Ireland. Legal experts pointed out that a president cannot strip citizenship of a native‑born American.

Way beyond insults, this was a direct threat to her legal status. Rosie fired back on Instagram, declaring she couldn’t be silenced. In other news, Brad Pitt demands to see Jolie’s messages in winery legal feud.

Rosie’s fierce reply

Rosie replied angrily, telling Trump to “go ahead” and comparing him to a “King Joffrey with a tangerine spray tan.” She emphasized that she has always spoken truthfully and will not be silenced.

The exchange quickly went viral on Instagram. That moment showed how her defiance remains strong. Fans are also talking about Billy Cyrus vs. Trace Cyrus: legal feud.

Whose side are you on? Drop your thoughts below.

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This slideshow was made with AI assistance and human editing.