That poor man! He's lucky to have you as a neighbor. (Something tells me he's a pretty good neighbor, too, or you wouldn't want to help him.)
I would go with honesty. Give him the money, gifts, whatever, and tell him he can pay it back when he gets back on his feet or by helping you with things that need to be done after the winter. I know if I were in his shoes, I would refuse an outright gift, but if it were couched as a semi-loan, I would accept for my child. I would not feel good about it, but I would want my kids to have a Christmas.
Another thought is to ask him to PLEASE let you take his kids shopping for a gift. I had a friend who did this for a family in California who were much like your neighbor. Their children were grown, no grandkids and they truly loved shopping with/for kids. So, to them, it was not doing a favor for their friends, it was a way to get into the Christmas spirit and keep some of their traditions alive.
Another thing you could do is pay his utilities for a month or two. This can easily be done without him knowing who did it snd, I'm sure, would be a great help. Leave a gift card or two on his door (but he may not use them if he's really proud).
Good luck and bless you for your kindness. May you keep the spirit of Christmas with you always and may your neighbor soon find a way out of this hole. Prayers are going up.
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Army/embassy brat - traveled too much to mention
Moved here from SF Bay Area (East Bay)
"There are only two ways to live your life: One is as though nothing is a miracle; the other is as though everything is a miracle." Albert Einstein
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