Jimmy Kimmel is taking a break from his late-night TV duties for the summer again, and in his place, a series of guest hosts will each fill in for a week. One of the fill-ins being brought in for Jimmy Kimmel Live! is none other than actress, comedian and media personality Rosie O’Donnell, and her hiring is garnering a lot of attention. Some individuals on certain ends of the political spectrum have had strong reactions to O’Donnell joining the show. Now, an expert is weighing in on the alleged principle behind the move. O’Donnell’s guest host stint was announced by Kimmel during the June 18th broadcast of his titular talk show, at which point he revealed his other replacements for his two-month vacation. At the time, the host quipped that as a “special treat” for U.S. President Donald Trump, he was bringing in “one of his all-time favorites,” Rosie O’Donnell, to “keep the hooks coming.” Kimmel’s comments were meant to reference the fact that O’Donnell had historically been critical of the president like himself. Public relations expert Christopher Lee – of the Foresight Strategies Firm – recently weighed in on Kimmel’s decision to bring in O’Donnell. While speaking with OK! Magazine, Lee said there were allegedly some key factors that went into Kimmel’s rationale for adding O’Donnell to the guest host list:Let’s be real about this. Very little of this is actually ‘organic.’ Both Jimmy Kimmel and Rosie O'Donnell take their shots at Trump from somewhere real and personal. Trump has used them as cannon fodder for years and O'Donnell literally left the country over it. That's actual conviction, not a content strategy.More on Jimmy Kimmel Live!(Image credit: Disney/Mark Seliger)Was Jimmy Kimmel’s Suspension Politically Motivated? Ex-Disney Head Honcho Bob Iger Finally Speaks OutO’Donnell also has her fair share of experience when it comes to hosting talk shows, as she headlined her own eponymous series from 1996 to 2002 and won multiple Daytime Emmy Awards. Then, in 2006, O’Donnell became a panelist on ABC’s The View, where she feuded with co-host Elisabeth Hasselbeck and got into heated discussions with others as well. O’Donnell eventually left the show in 2007 and has since been reluctant to return. Her experience and dissatisfaction with President Trump aside, the Harriet the Spy alum also seems to have respect for Kimmel, who she welcomed back after his suspension in 2025.Among the most vocal opponents of Rosie O’Donnell hosting Kimmel is political pundit Megyn Kelly, who reacted to the news on an episode of her podcast. Kelly called the roster of hosts – which also includes Colman Domingo, Tiffany Haddish, Ike Barinholtz, Anthony Anderson and Jelly Roll – as a “litany of left-wing comedians.” Yet Kelly specifically took issue with O’Donnell’s inclusion and laid out past political comments she’d made. As of this writing, neither O’Donnell nor Kimmel have responded to Kelly’s sentiments. This summer break comes from Kimmel after what’s been an eventful set of months for him and his staff. As previously alluded to, Kimmel’s show was suspended indefinitely in September 2025 after he made comments in regard to Charlie Kirk’s death. Disney reinstated the series days later after holding internal discussions with Kimmel. More recently, Kimmel joked about First Lady Melania Trump looking like a widow ahead of the alleged assasination attempt at the White House Correspondents' Dinner, and he received backlash after the fact.As for what Jimmy Kimmel Live! viewers can expect from these upcoming episodes, that remains to be seen. Tiffany Haddish and Anthony Anderson have hosted the show before, though Rosie O’Donnell, Colman Domingo and others are newcomers to leading the program. The stream of fill-in hosts begins with Haddish on July 6th at 11:35 p.m. ET, and O’Donnell will take to the desk, starting on August 17th amid the 2026 TV schedule.