He has the best street agent, Worldwide Wes, in his back pocket. As long as that relationship still exists, he'll continue to bring in who he needs each year.
I want to say there is a rule about only giving out a certain number of scholarships every 4 years or something like that, and that rule could get him in the future if he gets too many 1 and dones, but that's the only thing that'll slow him down.
As long as WWW has the connections with the top PG in each class or at least as long as he's able to get that connection opened, then yes Calipari will get that player.