Jimmy Kimmel’s Selection of Rosie O’Donnell as Guest Host Is More Than ‘Strategy’ Amid Donald Trump’s Late-Night Feud, Expert Claims

Jimmy Kimmel knew exactly what he was doing when he announced Rosie O’Donnell as one of his summer guest hosts.

O’Donnell is set to fill in for Kimmel beginning Aug. 17, joining a rotation that also includes Tiffany Haddish, Colman Domingo, Ike Barinholtz, Anthony Anderson and Jelly Roll. But Kimmel framed O’Donnell’s booking as a “special treat” for President Donald Trump, calling her “one of his all-time favorites” and telling the president, “you don’t do anything stupid while I’m gone. OK?”

The choice quickly became bigger than a guest-host slot. Megyn Kelly blasted the booking on her SiriusXM show, calling the lineup “a litany of left-wing comedians” and claiming Kimmel is “worried about his job security.”

O’Donnell’s history with Trump gives the booking an obvious charge. O’Donnell has long been one of Trump’s most recognizable celebrity critics, and her appearance gives Kimmel’s show a built-in political hook while he is away.

Christopher Lee, founder of Foresight Strategies, said the conflict has both real emotion and obvious incentive behind it.

“Let’s be real about this. Very little of this is actually ‘organic’,” Lee said. “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.”