The 'Inappropriate' Questions Kaitlan Collins Asked Trump That Got Her Banned During His First Term

CNN's Kaitlan Collins and Donald Trump have been locked in a bitter feud for years. The reason being simply that Collins asks some hard questions, and the president doesn't particularly enjoy answering them. In fact, while the CNN stalwart was covering Trump's first term, in 2018, she got banned from a press event after asking the divisive politician what his aides deemed "inappropriate" questions. Collins' line of questioning mostly focused on an audio recording between Trump and his former attorney, Michael Cohen, in which they discussed a hush money payment to a Playboy model with whom the president allegedly had an affair. It was a hot topic at the time, and Collins asked whether the former "Apprentice" host felt betrayed by Cohen and if he had any concerns about what else his former fixer might reveal to the public. She also questioned Russian President Vladimir Putin's reason for declining an invite from Trump. 

The president ignored Collins' rapid-fire questions, even as other reporters in the room eagerly awaited his responses. Not long after, the journalist was reprimanded by Press Secretary Sarah Huckabee Sanders and Deputy Chief of Staff for Communications Bill Shine, and informed that she was no longer welcome at the press event in the Rose Garden later that day. This hardly deterred Collins, however. The following year, the CNN reporter had Trump hot under the collar again when she pushed him for answers about who would ultimately be footing the bill for the border wall. "Right now our government is shut down over a demand from your administration that the American taxpayer pay for the wall," Collins argued (via CNN), reiterating that the president promised his constituents Mexico would be the responsible party. Unsurprisingly, the president clapped back with a sarcastic non-answer, further solidifying their ongoing feud.

In April 2025, the wrongful deportation of Kilmar Ábrego García to an El Salvadorian prison was a major news story. But, when Kaitlan Collins, who hasn't been afraid to go to-to-toe with members of Donald Trump's administration, asked the president if he was planning on orchestrating García's return to the U.S., Trump decried her as a "low-rated anchor," per The Independent, and then proceeded to have several members of his cabinet answer Collins' question in what appeared to be an attempt to humiliate the respected journalist, including by saying, "[The question] is asked by CNN and they always ask it with a slant." 

This wasn't the first time Trump got nasty with Collins while the cameras were rolling either. During CNN's 2023 town hall, she questioned the president about his controversial decision to ignore a subpoena ordering Trump to hand over classified documents still in his possession. In what was one of Collins' most awkward on-air moments, the divisive politician clapped back, "It's very simple that you are a nasty person," (via MSNBC). The moment went viral. And yet, Trump continued calling on Collins during press briefings. 

During an appearance on "The Weekly Show with Jon Stewart" in June 2025, the host suggested that the president might secretly like having her around during briefings, opining, "He needs to be challenged by someone that he thinks has some gravitas or authority. Otherwise, I don't think it challenges him." Collins agreed, divulging that she'd heard from insiders that Trump finds reporters who ask easy questions boring. "I think he respects tough questions and often takes them," she shared. "He won't come to me first, typically. [...] But he will eventually come to me, maybe two or three questions in."