would have been better remembered if he had retired before 2000

While this does happen now and again, Peter Schmeichel being an example from UK football where he had an incredibly successful career as the Man U goalkeeper then retired very soon after leaving the club, it's also evident in cases where "only the good die young" because it relates to the concept of "dying the hero or living long enough to become the villain".

Marilyn Monroe will be considered a pin-up beauty for all of time because she died young enough her looks never really faded. Elvis is remembered as the star he's portrayed as most of the time but still had his end of days image marred by his rapid weight gain.

Anyone who lives or does something long enough is likely going to end up being tainted either through their own fault or potential inaction as other peoples' fuckups can still cause a scandal that ruins someone.