The focus by PDT on the NFL and not on Puerto Rico is where he went wrong.  Also you are incorrect about the USS Comfort, it will be leaving Norfolk VA in the next several days and won't get to PR for another week/week and a half.  Lastly, he waited until late yesterday (9/27) to waive the Johnson Amendment that lets non-domestic craft from delivering supplies.  Did he botch this, probably a little, but he could of done a better job after just dealing with Houston and Southern Florida with no hiccups.