It’s probably the deception part. He has his own money that he can donate, but instead he dresses up like he’s hungry and yanks heartstrings, and people think they are buying a hungry man a hot meal. Then, he diverts the money to Castro (regardless of where he says it’s actually going). All funds donated to dictatorships support the dictator.
I very rarely give to a bum on the street. Figure my automatic monthly donations to a couple of homeless shelters downtown help more. On the few times that I have given to them, it is usually a cold bottle of water and a granola bar or something.
Although I’m always worried they might trade or sell it for booze or drugs. And now I guess I have to worry they might send it to Cuba now too.
And if he’s lonely - he could spend time serving food, etc. at the nearest homeless shelter. I imagine it would be too much for him to invite some of them to his place for a bite to eat or get a hot shower. Perhaps if they were Cuban?