What?
He's a gold member, no matter the way that he books, his account is gold.
That's true, but you can't attach your membership number to the booking. I tried via Citi, Hilton Honors, and calling the hotel. They can't even add the number under notes/preferences. I was Diamond, so I did get the upgrade. Not sure if it was because of status or because they couldn't find the Citi reservation even though I had a confirmation number. First time I ever needed a key card for an elevator.
We also ate dinner there, charged it to our room via Surpass and got points. The stay showed up on the HHonors site.