Like, do coaches now discourage players from aggressively jumping passing lanes? Or are ball-handlers just more careful with the ball? Or is there some other reason that there are only two players on that list retired after 2008 (or in Chris Paul's case, are still active).

If you look at the active steals leaders, LeBron is 200+ behind Chris Paul at 1,937, meaning he will probably crack the top-10 eventually, then there is a huge drop-off to Andre Iguadala who is in the 1,600's. The only other active player who appears to be a strong bet to someday join the top 10 is Russ Westbrook, who's at 1,442 - so he would need to average around 2 steals a game for 5 more years.