It’s a symptom of not having many vocal, public leftist figures in the USA. In the 90s you really only had like two people, Cornel West and Noam Chomsky. The radicalism of the 60s and 70s had long since been smothered by the reactionary 80s, so literally between the early 90s all the way until Sanders in 2016, there just weren’t a lot of public leftist voices.
West would be on TV in the 90s and 00s, which I think was a huge part of his legacy and image. He’d be on national TV saying stuff like systemic racism, or imperialism, and I remember he was even saying stuff about trans rights as far back as the early 90s. So he definitely had his place, I guess, but maybe he was one of the view that managed to fill the complete vacuum void of how empty/defeated the 90s were for leftists.
In any case, West’s just a personality figure who likes doing speeches and selling books. You’re right that he could retire now and have a mostly positive legacy. He’s been correct his entire career about structural racism, but in essence he’s just a professor and we can’t expect him to have been a revolutionary or anything.