A President has to lead, and work deals, which means compromise. A Leading President can generate public enthusiasm and pressure for a piece of legislation he wants, the Bully Pulpit, which doesn't mean offering an occasional sound bite. It means focus, and work, and effort to ask the other side what they want and where they can compromise, and if you can't generate public pressure on them, the legislation probably isn't popular.
I don't think Obama had enough experience with this process, nor did his "handlers". I also don't think he cared enough to give it much effort.