Yes, this is the most pub the Pirates typically get on PSAMP. Until they turn it around, this is their cross.
Diddy was talking about auto-tune or something something. Really, I don't care much for Diddy, or Puffy or whatever. Maybe the Pirates hat was just a sign that he's going back to re-adding the "P" and being P Diddy again.
If you want better jokes, go start your own blog, funny guy.