And now, Mr. Bezos is headed for the exit.
He’s not exactly fading into the mist: He will remain Amazon’s executive chairman and will no doubt remain a major force at the company in much the same way Bill Gates has after stepping down from Microsoft. But Mr. Bezos has, for a long time, seemed weary of the day to day, with an eye on all the things you become interested in when you’re one of the world’s richest people — such as space travel.
In comparison, Mr. Jassy is nothing if not earthbound, and will be even more so as he struggles to move Amazon into the next and perhaps most difficult phase of its trajectory.
In that effort, he has ample examples in Satya Nadella at Microsoft and Tim Cook at Apple. Both took over from great leaders and made their companies greater and their stocks more valuable, even if they lacked the charisma and bravado of their predecessors.
But those who have tangled with him note that Mr. Jassy hates to lose any deal in the very competitive cloud space, with one observer noting that he tries to “win at all costs.” To me, that characteristic has been table stakes for most players in his sector, which includes rivals like Oracle, Google and Microsoft, none of which are known for their manners.
Still, Mr. Jassy will have to be even more willing to play hardball, given the pressures to expand the empire that Mr. Bezos has bestowed upon him while fending off antitrust investigations and other efforts by regulators to curtail its ambitions.
Will Amazon continue to press into health care? Autonomous vehicles? Should it double down on its retail ambitions or move quickly into new markets like insurance and banking? Can it keep growing its massive work force. or will it have to soften the hard-charging, manic style perfected by Mr. Bezos?
That same steel will was certainly on display in a long interview I did with Mr. Jassy in mid-2019 about AWS. I have always preferred to talk to him more than almost any other Amazon executive, because he does not shirk from a debate or retreat to stale talking points. He also was not going to give an inch when it came to tougher topics like potential bias in facial recognition.