Frankly, I don't see Starfleet going out of its way to offer Riker anything after his performance in Chain of Command. He proved himself to be insubordinate, immature, apparently unable to flow the simplest command from his CO without pitching a hissy fit, and all of this at a point where Enterprise was potentially going into a combat situation. clearly he does not have the temperament needed for a command/leadership position. He's luck he didn't face a courts-martial after his escapades, and he was probably just lucky to have kept the job he had. Riker should never see anything even close to a starship command and would probably end up retiring from a desk job at best.
That's pretty harsh. I know Riker haters love to cite Jellico as an example of how Riker sucks, but Jellico was written to be an asshole (which is why they cast Ronny Cox, because he is so GREAT in those roles!).
I assume the writers intended for Jellico to be the villain in the Jellico-Riker dustup. We were suppose to be rooting for Riker. But it had the opposite effect on me. Although Jellico may have been a hard ass, I thought he came across as the mature reasonable officer, not Riker.
As a viewer, I thought Shelby and Jellico provided the one two punch that were extremely damaging to Riker’s reputation. What Shelby and Jellico said about Riker were spot on and it was devastating. But in the Trek universe, I suppose it didn’t really matter because what each said about Riker was between Shelby and Riker and Jellico and Riker.
As such, I think Jellico could have left out specifics of relieving Riker in the final report to Starfleet, maybe in part in gratitude, and in part to cover his own ass, because of his hubris going into the situation in the first place and also there was a whole crew, or at the very least the entire E-D command staff (who are all decorated Starfleet officers) and Picard, who would have sided with Riker.
You are probably right. Jellico didn’t seem like a petty or vindictive person. He would say what he said in front of Riker's face, but not behind his back in a report. He probably didn’t mention Riker’s petulant behavior in his report, so there would not have been a bad mark next to Riker's name.
That all said, I think if you wanted to take an incident in Riker's past that could have delayed his promotion, I think the Pegasus would be it. In fact, while Riker ultimately redeemed himself and did the right thing, the fact remains that he assisted Pressman. Picard actually put Riker in the brig, and Riker was going in front of an inquiry board to answer "tough questions," and Picard even says at the end of the episode Riker reputation was damaged, would probably loose a lot of respect, and would have to work hard to regain that respect, so that could explain why it took another 8 years for Riker to make captain.
Riker did seemed too comfortable in his position on the Enterprise. Riker was spoiled by the comfortable situation that the Enterprise provided him. Picard ran a relatively lenient, laid back operation. Picard would have been a good captain for a pleasure cruise ship.
Shelby was right when she said, “All you know how to do is play it safe. I suppose that’s why someone like you sits in the shadow of a great man for as long as you have, passing up one command after another.”
Riker should have been prosecuted for what he did on the Pegasus, like Pressman was. However, Riker got away scot-free. He was put in the brig, but it was only symbolic. Picard let him go. Riker was spoiled by Picard.
I don’t blame Picard for Riker’s insecurities and for Riker's behavior that were unbecoming of an officer, though. Riker couldn’t deal with the likes of a Jellico, so Riker acted up, imho.