I'd rather have the former. Kerr made over $16 million in his career according to Basketball-Reference and parlayed that career into a job I think most of us would love to have (or at least attempt). He did it while playing with the greatest player ever, on one of the greatest teams ever, and yet with no real outside pressure (media, fans). He made a title-winning shot on one of MJ's most famous plays, when MJ told Kerr he was going to him if MJ got doubled in advance. He even had a throwback game in the '03 Finals, hitting a bunch of threes to help SA get a title in his last year. Granted, I'm also factoring in things like "I'd be able to live a relatively normal life because I wouldn't be constantly surrounded by fans" and things like that, but I'd much rather make 16M and win a bunch of titles than make five times that (and really, how much can you spend?) and never win anything, even if it means I'm not as famous.