No one ever said Jobs was stupid.
He was a left-winger though, which makes sense. /s
A lot of high-achiever narrow-talents lean to the left politically. It’s like buying your politics in a package deal. You buy into it and then forget it. Repeat the proper pieties when you are forced to talk about politics, and everyone agrees and leaves you alone.
Obama is a leftist. There's a big difference between a cultural lib and a committed leftist. Unfortunately, cultural liberals are responsible for electing leftist ideologues like Obama. Jobs probably thought Obama was just a smoother version of Slick Willie...someone who would back down and shift towards the center when their policies proved stupid. He, like millions of other cultural libs, didn't realize that Obama is a hard leftist.