Originally Posted by Mustard
I've never understood the argument that a player who carries on playing as their results decline "damages their legacy". Any results they have made in the past are not removed by playing on.
For example, I've heard some people say that Connors should have retired after 1984. Why? What he did up to 1984 will always be there whether he had stopped at the end of 1984 or carried on well into the 1990s, as he did. I believe that by squeezing every last drop out of his potential, surely he increased his legacy all the more.
While Roddick did NOT wait too long to retire, he does show how sticking around could hurt a player's legacy. Young Roddick was known as a huge hitter, biggest server, and a kid with a ton of talent.
Now, a lot of people think of him as lacking a lot of talent on groundstrokes, less talented that other top players, etc. When players' abilities start diminishing, people remember them as less successful and talented than they would have if the player had quit closer to their prime.