It's not okay for an AD to keep whiffing on his hires, never getting one of his top choices. No matter what condition we're in, that's not called success. DW is getting paid a lot of money to hire his third, fourth, or fifth choices. The whole point of bringing him in, in paying him more than most other ADs, was his supposed ability to "get his guy". That's not to say things won't still work out. But he hasn't landed "his guy" on multiple tries.