He runs the Clippers as a business, not as a sports team. He bought the organization for very little, has invested next to nothing in it - paying among the lowest salaries in the league - and now has an entity that is reported to be worth north of half a billion dollars. While he might not be successful in terms of titles, he has been very successful in terms of making money. So I guess it’s just what the definition of success means.
His investment went up, but not because of his efforts. The value of the Clippers went up because the value of the league went up, and it's in a major market.
Exactly. He appears to operate the team as a business. He doesn't care if they win, he cares about maximizing return on investment. If that means not spending too much for players, then that's his business decision.