Hate him or not, Steve Jobs understood humans. He spoke and behaved as a human. He was flawed and may be considered "cringey" now, but I think he'd be liked better than the rest.
His Apple keynotes conveyed a sense of magic, for example demonstrating pinch to zoom on the iPhone and pulling a MacBook Air out of a manila envelope. And something he'd be angry because things didn't go as planned.
These pre-recorded keynotes we get nowadays are just bland and AI-generated.
Steve Jobs? The guy who was adopted by working class parents, a hippy, with a Syrian immigrant father? I think he might view the world slightly differently than the guys born into wealth, who went to Ivy League schools, and who all seemingly share the same total inability to understand ordinary human beings.
As opposed to the current guy who gifted a custom 24K gold plaque to the current administration, after being raised by a shipyard worker and pharmacist and attending a public land-grant research university in Alabama.
When it comes to business, I think Jobs would grovel at the feet of Trump just as much as Cook has.
Yeah Steve Jobs was deeply frustrated with Obama when he got to meet him. Jobs hated unions, and felt like the Obama administration was not business friendly enough. He also felt the Obama administration was too reluctant to offend people.
He didn't live long enough to become the bad guy, but if he were alive today, I think there's a near-zero percent chance he'd support Clinton or Biden over Trump in either of those elections.