Maybe he has an insider in reservations willing to do manual overrides for him?
Back in the days of the UA 1k rooms at airports, those ladies could work miracles if they liked you. Colleen at the DEN 1k room used to regularly open up F seating for upgrades for me.
And the angels at the SEA 1k room were famous system wide for taking care of us by bending the rules when need-be...