It's possible the front desk would just store the bags (thus they would get the tips when I retireve them), but I am sure the union contract would prohibit that. The front desk would probably just take $1 out of petty cash and give it to the bellman.

They probably would do it for all Diamond members that asked. Just like airlines will waive checked bag fees and same day confirm and standby fees for their top level members.

Not really a big deal now at this property. Seeing the $1 is in the union contract it is obvious it is going right to the bell staff (no union is going to put a customer fee in their contract if it isn't benefiting them). When I stay at that property in the future I will simply tip $1 less than what I normally tip. If the $1 tip fee goes into some kind of pooled fund and gets dividided up between the staff periodically instead of going right to the person that took the bags, oh well, they voted on it. I normally tip $3 for one bag (which is usually a carry on rollar bag) and $5 if I check my backpack with it. Now I will just tip $2 or $4 instead. I am not out any more $ and the bell staff is still getting the same $.