Tread lightly when offering your sympathies for someone's bankruptcy by taking an example from this financial condolence letter.
Dear {Recipient},
I was so sorry to hear about the recent difficulties that you and your family have gone through. I know that it is a sensitive subject, but I just wanted to lend my support and let you know that I am always here to network or help in any way I can.
Our economy may be doing horrible things to us, but I have always looked up to you as someone with smarts, good sense and more talent than {he/she} knows what to do with. I have no doubt that your hard work and tenacity will help you through this difficult period.
Love,
{Sender}