It's hard to feel for a guy like Randy, with his past being as checkered as it is. But part of me does, as I believe he's sincere about wanting to win. I love to see the Raiders turning into a wasteland thanks to an owner who the game has passed by.
There was a lot of good press about the guy going into the season about the way he was preparing and taking on his role as a team leader. But with the Raiders complete lack of commitment to actually winning, I can imagine that would make even the most seasoned of veterans frustrated, let alone a hot-dogger like Randy who is trying to transition from his previous self to a team leader.
I think that when the time comes for Randy to leave, he's going to go with a perspective that appreciates the opportunity to go to a winner, realizing that winning isn't automatic just because Randy Moss is on the scene.
Shanahan considered Terrell Owens, but when they brought him in for an interview, his complete lack of perspective and inability to show any remorse for how he left the Eagles organization turned him and Sunny off. As a result (thankfully) Javon became their top receiving focus. With regards to Moss, I think the way he interviews will be the difference between whether the Broncos will want him or not. He's not a great route runner, but he could easily fill in the role that Lelie had on this team.
That said, I doubt we'll see Randy Moss on this squad. I'd wager on Lelie coming back before I would on the Broncos signing Moss.