First Trump administration and 2020 re-election effort
In December 2016, it was reported that Guilfoyle was being considered for the position of press secretary for President-elect Trump. Sean Spicer was considered the front-runner for the position, and was ultimately selected. On the May 12, 2017, edition of The Five, co-host Bob Beckel hinted that Guilfoyle turned the job down. In an interview with Bay Area News Group on May 15, Guilfoyle confirmed she was in contact with the White House about the position following Spicer's resignation. On May 19, 2017, Guilfoyle said she was under contract with Fox, indicating she turned the White House down. One month later, she extended her contract with Fox.
In 2018, The Washington Post called Guilfoyle a "conservative cheerleader for President Trump". In 2019, Guilfoyle and Donald Trump Jr. jointly toured school campuses, invited by venues such as the University of Florida, where they were paid $50,000 for their appearance from student activity fees, which led to complaints by anti-Trump students. At the event, two people were arrested and five were injured.
In 2020, Guilfoyle was reported to be the chair of the finance committee of the Trump Victory Committee. As of early 2020, the Trump campaign was secretly paying Guilfoyle $15,000 per month through the campaign manager's private company, Parscale Strategy. Guilfoyle served as a surrogate on the stump and took on broad advisory roles. In the Trump 2020 campaign, she managed a fund-raising division. This division paid socialite Somers Farkas to raise money. The fundraising division Guilfoyle managed was in internal turmoil amid departures of experienced staff and accusations of irresponsible spending. In November 2020, Politico reported that Guilfoyle had engaged in sexually explicit conversations during private Trump fundraisers that had made some attendees uncomfortable. Politico reported that many campaign insiders alleged that this was part of severe human resources problems that plagued the fundraising division, likely damaging the Trump campaign's ability to keep pace with the Biden campaign's fundraising.
At the Republican National Convention in August 2020, Guilfoyle gave a speech endorsing Trump that was widely described as unnecessarily loud or unhinged. Others in media described it as passionate. She was criticized for describing herself as a first generation American when her mother was from Puerto Rico and thus a U.S. citizen. She is a first-generation American on her father's side, as he immigrated to the United States from Ireland.
On January 6, 2021, Guilfoyle joined Trump, Trump Jr., Rudy Giuliani, Eric Trump, and others on the Ellipse in Washington, D.C., to address the "Save America March." This resulted in the attack on the Capitol. Having raised millions of dollars to support the rally, Guilfoyle was also involved in organizing the protest at the Capitol. She was paid $60,000 for her rally speech, lasting less than three minutes. Guilfoyle was featured in a video screened at the rally by Trump Jr., "break[ing] into the hip-shaking dance she's been showcasing at other recent pro-Trump rallies" and "tell[ing] Trump fans: 'Have the courage to do the right thing! Fight!'"
