Probably ill prepared for the current cold weather in Tucson. A thick warm coat and a thick warm sleeping bag...maybe used from Goodwill...with some plausable story about why you don't need them anymore.

Cash is nice too, if he's not a boozer...or canned goods - something he can keep/stash.

Probably some sort of homeless outreach in Tucson. They may have ideas.

So many of us are one paycheck away from where he is...worked with homeless for years...scary - could be any one of us....