Bob Iger likes sailing metaphors, as befits a man who is passionate about his yacht. He also enjoys employing them when discussing his own legacy, or his storied career at Disney, which is about to come to an end next month. Two weeks ago, while hosting a goodbye dinner for friends (Steven Spielberg, Al Michaels), colleagues (Bob Chapek, Peter Rice) and various Disney talents (Jimmy Kimmel, Robin Roberts) in the garden of his stately Brentwood mansion, Iger toasted the “many great sails” that he and the Disney team had been on together, and “all the ports” they’d been in, sources who were there that night told me. Guests dined on swordfish and chicken parmesan and were treated to a mid-dinner medley of Disney songs performed by the famed violinist Caroline Campbell. Then they bid Iger adieu as he sailed off into the sunset.

Back in Burbank, of course, the mood is less sentimental. Some at Disney are in a state of dread about their new boss, and the changing nature of their business. Iger succeeded in casting himself as a charismatic and talent-friendly leader who trusted Disney creatives to run their own show, and go with their gut. Chapek, who was named C.E.O. last February, is seen as a shrewd, data-driven businessman who is laser-focused on the bottom line.