Year: 2009
Net worth: $150 Million

Talk about throwing shade. According to Andre Agassi’s autobiography, Open, former rival Sampras was “dull,” “robotic,” and “lacking inspiration.” But perhaps the worst jab dished out from the former World No. 1 was the story he told about Sampras’ alleged slight of a valet. Agassi recalls that Sampras once gave a valet a $1 tip for fetching his ride. You probably could’ve pulled out at least a fiver there, Pete. Still, why did this little anecdote belong in Agassi’s book to begin with?