I’m not going with stats or money as criteria but…
Rondo - title for Boston and LA pretty incredible run he had. Not sure anyone saw him having the career he did. Hearing players talk about rondo now on various podcasts is pretty cool. They all really respect him.
Tayshaun - helped Detroit win a title on a team that’s one of the great sports stories in modern times. Bunch of misfit players, no huge stars, took down giants. Also Tayshuan was a unique player about a decade before his build and skill really took off in the league and game in general. He was the 3rd-4th option and today would be #1 and franchise player.
Chuck Hayes - Incredible he had a career. Didn’t really have a position. Undersized, not long, not as athletic, quick/fast, etc…but managed to have a real career. Kind of opposite of Tayshaun in that the Chuck Hayes archetype player went extinct and every team has or wants multiple Tayshauns.