I don't know, I'd probably go the more direct route, but I guess that's me. I'm ok with making people uncomfortable-especially if they really need the help. Only because they're may be programs out there that can permanently help him. You could build a relationship with him and talk about programs slyly eventually.

For example many of the items are specific to my state, but some are not.

Energy assistance- they get a chunk of money several times per year on their energy bill and it's income dependent- they may get several hundred dollars every year when they fill out the form and send income verification.
Also if you live somewhere hot, they may replace/fix his a/c for free

Lifeline- free cell phone or about 10 buck off a landline every month

Senior tax deferral- senior pays a portion of their taxes, but the rest accumulates and is payable when they sell the home but they get to stay there until they are ready to sell.

Food shelves- some states are great, some are not for this

These would make a long term lasting source of help rather than a temporary fix. I'm sure there's things in whatever state you're in that you didn't know existed.

Call 211- United way and see what kind of programs are available. Someone mentioned a senior center, it's possible they may help but not necessarily.

I'm just thinking the guy needs permanent sources of help not just a one time thing.