Even When Our Brother is a Loser
Yes, we are our brother's keeper economically and in all ways. Indeed, we are taught by the rabbis that you have to continue to help your brother even if he needs your help time and time and time again -- even if he is a continual loser.
Our duty is to do what ever we can to save him from destitution (an obligation on us all), to help him get on his feet again, and -- the highest order of Maimonides' eight levels of charity -- to give him the wherewithal and the opportunity to start a business/get going again so that the never has to ask for charity again.
It is worth pointing out that this is not only because of the kindness of our hearts, or indeed because of divine instruction, but also because it helps the community in which we live. So, however much we may resent helping those who have been careless and possibly absolutely delighting in risk taking, we have a duty to help for the sake of society.
March 3, 2009; 10:37 AM ET
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