Inside Donald Trump's Decade-Long Feud with Rosie O'Donnell

This Week in 2007 is a weekly column looking back on Lindsay Lohan, the first iPhone, George W. Bush, and everything else we loved about the year 2007.

Before Trump and O'Donnell battled it out in the political sphere, they were acquaintances. Trump and his second wife Marla Maples even attended the 1994 opening of a Broadway revival of Grease starring O'Donnell as Rizzo. Before he descended into Birtherism, Trump once mingled with hordes of New York-based celebrities. King of the Paparazzi Ron Galella—best known for capturing a barefaced Jackie Kennedy—shot an art book's worth of images of Trump with Joan Rivers, Barbra Walters, and hoards of other New York social scene luminaries.

Of all the Manhattan belles, Trump probably had the most in common with O'Donnell. He was born in Queens, she in Long Island; both strived for more. Yes, Trump was the scion of a real estate tycoon, but his outer borough status haunted him. According to McKay Coppins's extensive BuzzFeed feature, Trump purchased skyscrapers in the city because of his class anxiety about growing up across the river. His insecurity was somewhat valid. Last year, the Boston Globe reported Trump's Wharton classmates rolled their eyes when he revealed his plan to become "the King of Real Estate." It echoes themes in O'Donnell's second memoir Celebrity Detox: The Fame Game. Written partially in verse like an epic poem, the book describes O'Donnell's longing to escape Queens and become a star, unaware of the downsides that come with celebrity.

It's unclear when the bridge and tunnel stars started hating each other. (White House Director of Strategic Communications Hope Hicks did not reply to Broadly's request for comment. In an email, O'Donnell declined to comment and directed Broadly to her tweets, both her and Trump's preferred medium of the moment.) Their war became public in 2006 and 2007, when O'Donnell endured public attacks for her critiques of the Iraq War made on The View, where she worked as a co-host.

In December 2006, a few weeks after O'Donnell and her fellow co-hosts celebrated Britney Spears filing for divorce from Kevin Federline on national TV, Trump had announced his decision to let Tara Conner keep her Miss USA time after drug allegations emerged. On December 20, O'Donnell mocked Trump's handling of the controversy. She called him a "snake-oil salesman on Little House On The Prairie" and accused him of going bankrupt. (Trump has never filed for bankruptcy, although his companies have six times.) "[He] left the first wife, had an affair," O'Donnell said. "[He] had kids both times, but he's the moral compass for 20-year-olds in America. Donald, sit and spin, my friend."

Trump could have let her comment go. Considering he allegedly once pretended to be his own publicist, Trump probably knew responding would create more press ruckus. Later that day he told People magazine: "You can't make false statements… Rosie will rue the words she said. I'll most likely sue her for making those false statements—and it'll be fun. Rosie's a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie." Instead of discussing Trump's Miss USA scandal, the media buzzed about his feud with O'Donnell. As the media has accused Trump of doing as president, Trump misdirected the public.

But he did not let go of O'Donnell's statements about his finances. Throughout 2007, he continued to taunt her, becoming a frequent talking point on The View. When O'Donnell fought co-host Elisabeth Hasselbeck because she would not answer whether she thought O'Donnell believed "our troops were terrorists," Hasselbeck redirected the argument to Trump. "It's much easier to fight Trump!" she snapped at O'Donnell. "Because he's obnoxious!"

Trump viewed the infamous talk show deathmatch as an opportunity to offer O'Donnell a backhanded compliment. "On this one I think Rosie should win, but Rosie is not much herself," he told EXTRA. "I think anybody that's against the war in Iraq is the winner of the fight, because to justify the war in Iraq—only an imbecile could do that." He was still insulting O'Donnell, but the root of his hatred seemed more and more unclear.

Since 2007, O'Donnell has remained one of Trump's trademark obsessions. O'Donnell announced her second marriage in 2001; Trump tweeted, "I feel sorry for Rosie 's new partner in love whose parents are devastated at the thought of their daughter being with @Rosie—a true loser." O'Donnell went into heart surgery; Trump tweeted, "@Rosie get better fast. I'm starting to miss you!"

"r u trying to kill me?" O'Donnell wrote back.

She was kidding, but over the years, Trump's nasty remarks have harmed O'Donnell. He has attacked her numerous times on Twitter since 2007. In 2014, he ranted about O'Donnell's hypocrisy for feeling "shame" about her weight although she had mocked former View co-host Star Jones. "Go away," O'Donnell tweeted at him. Later that same year, he called her "crude, rude, obnoxious, and dumb," because ABC had announced she was returning to The View. Looking back, O'Donnell has described how Trump's comments affected her self-esteem. "Probably the Trump stuff was the most bullying I ever experienced in my life, including as a child," she told People in 2014. "It was national, and it was sanctioned societally. Whether I deserved it is up to your own interpretation."

The trend mirrors what happened to Megyn Kelly after Trump verbally sparred with her during the first Republican primary debate, where she asked him about his previous sexist comments. (Trump also dragged O'Donnell into the debate, saying "Only Rosie O'Donnell" when Kelly accused him of calling women "fat pigs.") Trump's fans harassed Kelly on Twitter, and she took two weeks off the air. (She also hired bodyguards.)

Trump's pettiness, of course, goes back decades. Wayne Barrett's book, Trump: The Greatest Show on Earth, describes Trump's "petty dispute" with an architect in 1984. Trump holds grudges, like his current one against media outlets that have published disparaging articles about him and pointed out the low turnout for his inauguration. In January, the Washington Post accused Trump of using his feud with the media to misdirect the public about his alleged relationship with Russia. Trump sees his obsessive feuds as a tool to push his agenda and boost his fame, but they often come from his own wounded ego. He's even stated that his feud with O'Donnell goes all the way back to her comments on The View in 2006 and 2007. "Remember," he tweeted at O'Donnell in 2004, "you started it!"