When I was in the Army maybe once every 2 or 3 months my sister would call me asking for about $100 to help cover rent or a visit to the vet for her dog or some random unexpected thing.
Turned out she was buying hard drugs and I learned about it when I came back on leave and she was back living at home with my parents going through withdrawals. She basically got clean, got back on drugs, and finally got clean for a final time over the next few years after I found out but I've never sent her money again (and when she was back on the drugs you better believe she asked for $).
Turns out she had done the same thing to my parents far more frequently but I was just her fallback when they said no.
To be honest if this the very first time he has asked you for cash I would give it to him. If it becomes a pattern I would cut him off even if you can afford to do it.
~ IN THE FUTURE there will be no black people and white people. Just robots.
Get to your staging points and be ready to invade the North