Yep, I think “recipient” would have been a better word than “winner”, but that is probably beyond gibbs’ intellect.
The HOA sucks lemons- “aesthetics” leaves a lot of wiggle room- surely enough room to allow the flagpole to be maintained by someone whose military career was as distinguished as this gentleman’s was.
i’ve been having trouble finding a good picture of the entire flagpole in context of the neighborhood, so it’s hard to judge whether the flagpole fits with the decor of the community.