Disney CEO Bob Iger is in a no-win situation with Jimmy Kimmel on one side, the Trump administration on the other, and Disney’s reputation hanging in the balance. Jesse Grant/Getty Images for Disney

At ABC’s annual presentation for advertisers last year, Jimmy Kimmel looked over to his boss, Disney CEO Bob Iger, and made light of Iger’s return to the company after stepping down from the CEO post in 2020.

“Bob Iger, this guy, he should be retired by now,” Kimmel joked. “You should be off on a yacht somewhere!”

Seriously, though, that yacht probably sounds pretty good to Iger right now. Remaining in retirement wasn’t really an option for the restless Iger. But some fellow execs are wryly wondering if he regrets being back on top right now.

Iger, 74, who once wanted to run for president

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