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Several questions to ask.
How did he end up broke?
1) Did he buy some new fancy toy that he doesnt need?
2) Spend to much time with the buddies drinking and partying.
3) Is he in school and had some unexpected school costs?
4) Lost his job and there were more important bills to pay then the insurance?
The first or second one I would pay it on one condition. Has he ever come to you for money before now. If not then hes just made some bad money decision this time round. But specify that the only reason you are doing this is because this is the first time hes come to you for money. Let it be a financial lesson and tell him that you are not going to continue to be there to solve his money problems. If hes constantly asking you for money even though this is important tell him forget it you are tired of pulling him out of the money hole and its about time to realize that theres more important things then partying and having fun.
If he falls into the 3rd or 4th I would definately pay for it. He needs his insurance to look for another job and to get back and forth to appointments.
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I couldnt think of anything to put here , but I guess anything would do
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