Ryan D’Agostino Profiles Tim Cook for Esquire on Apple’s 50th

Ryan D’Agostino, writing at Esquire:

Cook was at Jobs’s house the day he died. As he drove back to the office to announce it to the employees and, in so doing, to the world, he felt a strange kind of shock — strange because Jobs had been sick for so long, had even refused medicine when he was first diagnosed, instead trying to cure the disease with fruit juices, and so there should have been no shock at all.

“By that time, unfortunately, there was an inevitability to it,” Cook says. “But I was in denial for so long about the disease and where it would go, because I had watched him bounce back so many times, I assumed he always would. When I took the CEO role, I thought he was going to be executive chairman forever — that’s what I thought literally six weeks earlier. Looking back, I know somebody could say, How could you think that, given the circumstances? But that’s not the way I was wired in that moment.”

D’Agostino, fondly recalling the Apple IIe his family got for Christmas in 1983, wrongly remembers that, “When we turned it on, there was a little trash can in the corner of the screen.” Don’t let that conflation of the IIe and the Macintosh (yet to come in 1983) turn you off. It’s a good profile. Cook’s thoughts on Steve Jobs are touching, and D’Agostino gets Cook to expound upon his strategy of “engagement” with the Trump administration to a degree that I don’t think any other interviewer has. Cook’s answer is over 400 words, and Esquire, to their credit, ran the whole thing.

★ Wednesday, 1 April 2026