Jobs made several poor decisions around Apple's stock, including after he came back. A few choices cost him billions of dollars (which would now be tens of billions for his wife). Fortunately for him, money wasn't something that he obsessed over.

You're talking about a guy who got in trouble for having his subordinates make up a fictitious board meeting to get a better strike price for his options.

http://www.forbes.com/sites/timworstall/2011/10/06/steve-job...