I mean, Booker isn't Curry, but neither is Jaylen who he was being compared to Kawhi or Lebron. The reason you can't win with Booker as your best player isn't that you can't win with a scorer who is below average on D, it's that he hasn't reached the elite tier as a scorer yet.
I think the bigger issue is that you think Booker is a black hole, which I don't think is really the case anymore, he's significantly improved from his first few years. If we're just saying, what teams have had their best player be a negative defender and be contenders... GS, HOU, DEN, POR, TOR (DeRozan), BOS (IT year) have all made the Conference finals with their best player being a negative defender. It would probably be more but I credit LeBron as a positive defender and he's taking up one of the spots every year.