It’s more the requesting bit. I’d be happy to buy what would probably be a $150 shirt or sweatshirt but the act of requesting it feels odd. If I were already in contact with a few seniors with a knitting/sewing hobby then it would be perfectly kosher, but soliciting clothing feels exploitative, unless it’s handled carefully.
If you can dodge criminal discharge of a firearm, you can dodge a bill. Seriously though, how did he manage to blow through his speaking money? I’d read that he’d earned 10k on several.