He has a VERY comfortable gig with NBCSN, where he is paid really well and gets to spend a lot of time with his family. Apparently an Assistant GM job would be a pay cut for him. Those two factors combined (time, money) are probably the reason why.
Owners seem reluctant to hire someone who has not been a part of an organization for 15 years. If he were to take a job as an Assistant GM he would probably be hired as a GM after 2-3 years. He interviewed for 6-7 teams over the last several years. Was the runner-up choice to be Canadiens GM, was almost hired to be Pittsburgh's GM but he wanted a longer contract and Pittsburgh only wanted a stop-gap sort of GM for two seasons. Always the bridesmaid, never the bride.
I'm not a huge fan of him on television, but try listening to him on the radio. He's much more calm and not over the top. He's on every afternoon on TSN radio in Montreal and several other places, and he definitely knows his stuff.
The article people keep talking about is from 20 years ago, and he was hired by Ottawa the same day he got fired in Hartford. He was also an assistant coach for the Pittsburgh Penguins when they won 2 cups.
This guy gets it. Pierre could have had the Pittsburgh gm job, but he wanted longer term due to his comfortable gig at NBC, which allows him to spend time with his family more often. Listening to him on TSN 990, 1290, and 1200 is a pleasure. The man knows hockey, and as others have said, he has the mind and the knowledge to be a gm