Late-night host Jimmy Kimmel is stepping away from his desk for his annual summer break. But before leaving, he has arranged a farewell gift specifically designed for President Donald Trump. Kimmel seems to have picked one of Trump’s fiercest critics to replace him.
Jimmy Kimmel announces Rosie O’Donnell as host during summer break
Jimmy Kimmel revealed the handover plan during his Thursday monologue, confirming that Jimmy Kimmel Live! will continue with a rotating cast of guest hosts across his two-month vacation. Familiar names like Anthony Anderson and Jelly Roll are set to return. However, one particular booking stands out, aimed squarely at the White House.
“As a special treat for our commander-in-chief, I asked one of his all-time favorites, Rosie O’Donnell, to be here,” Kimmel said. He followed the announcement with a childlike warning to Trump. “And all I ask in return, Mr. President, is that you don’t do anything stupid while I’m gone,” Kimmel added.
Rosie O’Donnell has been a fierce critic of Trump for decades, long before his political career began. During her time as a co-host on The View in 2006, O’Donnell famously attacked Trump’s character and personal life on air.
“Left the first wife, had an affair, left the second wife, had an affair. Had kids both times,” O’Donnell said at the time, before adding sarcastically, “But he’s the moral compass for 20-year-olds in America.” She also branded him a “snake-oil salesman” for his treatment of women (via The Daily Beast).
The animosity is mutual and well-documented. President Trump has repeatedly insulted O’Donnell’s appearance for years. The feud escalated in September 2025, when Trump posted a heavily edited image of O’Donnell on Truth Social, writing, “giving serious thought to taking away Rosie O’Donnell’s citizenship.”
Moreover, Kimmel’s decision to hand O’Donnell the microphone carries extra weight given recent events. The show was briefly pulled from the air in September, and Kimmel referenced the controversy obliquely while announcing his time off. “I will be taking the next two months off,” Kimmel stated, before emphasizing, “This time voluntarily.”
Originally reported by Devanshi Basu on Mandatory.
