Bob i'm praying for your buddy and wanna share a thought. In my life it seems it has been hard to reach my old hard charging party friends and it reminds me of Jesus word's in
Mark ch6
Jesus Rejected at Nazareth
1Jesus left that part of the country and returned with his disciples to Nazareth, his hometown. 2The next Sabbath he began teaching in the synagogue, and many who heard him were amazed.
They asked, “Where did he get all this wisdom and the power to perform such miracles?” 3Then they scoffed,
“He’s just a carpenter, the son of Marya and the brother of James, Joseph,b Judas, and Simon. And his sisters live right here among us.” They were deeply offended and refused to believe in him.
4Then Jesus told them, “A prophet is honored everywhere except in his own hometown and among his relatives and his own family.”
5And because of their unbelief, he couldn’t do any miracles among them except to place his hands on a few sick people and heal them. 6And he was amazed at their unbelief.
Sometimes the people who have been close to us thru life see the change in us when we are trying to follow Christ, but also when they look at us see there old friend who use to do all those crazy things with them.
Maybe you know a pastor/priest friend who doesn't know your friend who would be willing to go spend some time with him, sometimes its easier to open up to a complete stranger than to a old buddy from your "hometown"
just my 2 cents
praying for your friend