Insurance Co are such finicky groups. Out for the bottom line and often the patient is the one stuck in the middle. I realize it is a business but when it is your health on the line you kind of resent that. Have your frien look into legal help. The Ins. Co have more money then him so this could become a war of money. He needs good legal help and a lot of emotional support. Gather his friends and co-workers around and let him know that you are with him on this. Maybe not financially but emotionally. This will be hard on him and his family and it helps to know that he is not alone.
My prayers are with him and his family.
Worry not for tomorrow, for tomorrow will take care of itself.
Remember healing comes one step at a time, sometimes it seems that its one forward and 2 back but ultimately, always in a forward direction!!!