This is such a difficult and interesting question to try and answer. Of course, I can only offer my viewpoint as someone who worked for (with?) him in four diff

This is such a difficult and interesting question to try and answer. Of course, I can only offer my viewpoint as someone who worked for (with?) him in four different contexts. He was most definitely not empathetic to me. He could be very empathetic to an abstract construct of a person. He would act as an advocate of the "user" but I felt that the user was always him. How did this align with reality? I guess it did, to a certain cross-section of people who appreciated whatever guise of a user Steve represented. This user construct changed over time and I could see it in early Apple Steve, lost in the wilderness Steve, NeXT Steve and return to Apple Steve. Steve had charisma. Younger Steve charisma was different to me and it left an imprint. I felt that he was attractive physically and mentally, could engage with you and make you feel like you and he were doing something that could really make a difference. We knew we weren't curing cancer, but that somehow the pursuit was noble in a similar way; enabling human potential that was being lost. I still want to feel this way about technology. Once you got to know Steve (if one could) he was oddly two-dimensional. His lack of real personal connection or concern about you as an individual was troubling. In some ways, the more abusive he was to you, the more it showed his interest in you. It was dysfunctional. He was never mean to random people (in my observance) although you hear stories of him being abusive to people he didn't know, I never saw it. I saw him open doors for people, let people cut in line in front of him in the salad bar, normal sorts of politeness. The higher his expectation of you, the harsher the abuse you could expect to receive. You could never really become numb to it, but after awhile you just began to adjust your calibration. As you point out, Steve did win quite a bit. Of course he lost and sometimes he lost big. I really didn't care about winning the way a lot of Silicon Valley people care and I saw some of this in how Steve lived his life. Yes, he drove a nice car and had some property. But he wore well-worn clothes, drove himself to work and generally seemed like one of us. Later in life, odd things like private jets, yachts and Central Park condos showed up. Everyone that I worked with at Apple who is still there knows it is not the same company. It can't be. The scale, management structure, market, political climate and more is different. And there is no Steve. I left Apple when Steve finally left, but I knew that "my" Apple was gone around 2006.