OK, so seriously. TNG: The Pegasus.
The core plot of the episode was drawn from Raise the Titanic! While breaking the story, Ron Moore decide that Riker had been on the ship when it was lost, and there was something to hide, adding a level of intrigue to the tale. He noted the similarities between Riker’s dilemma here are Wesley in The First Duty, and that Wes didn’t have the luxury of an illustrious career to save him from disgrace like Riker did. He also joked that he’d written yet another rogue Starfleet, and wondered if they were putting something in the water at Starfleet HQ.
The teaser was originally going to have Data, Troi and Riker practising Pygmalion, but Michael Piller nixed the idea. Moore then struck on the idea of Captain Picard day, primarily to allow Jonathan Frakes to use his Picard impression on-screen.
This episode was directed by LeVar Burton, the second (and final) TNG one he would direct. His other episode was Second Chances, also a Riker-centric story. After TNG wrapped, Burton would go on to be a regular director for Trek, helming 10 episodes of DS9 between series 4 and 7, 8 episodes of Voyager, and 9 of Enterprise.
This episode marks the first time there’s a solid explanation for why Starfleet ships don’t carry cloaking devices. Moore decided that a treaty was the most rational explanation as opposed to some technobabble, or Gene Roddenberry’s preferred reason - that the show’s heroes “don’t sneak around”. While it wasn’t planned, the episode The Next Phase foreshadows this one, the Romulans are experimenting with a phasing cloak in that story.
Michael Mack becomes the first black actor to play a Romulan in this episode. His skin is lightened somewhat with makeup though.
Terry O’Quinn impressed the producers so much in this episode they considered bringing him back for an episode or two of DS9, but it never came to fruition.
The entries for Captain Picard day were sourced from two local schools and the children of the show’s property master.
Pegasus was originally going to be a Cheyenne class starship, one of the designs worked up for the graveyard at Wolf 359 in Best of Both Worlds, part 2. It was decided to switch the ship to an Oberth class so they wouldn’t have to make a new model for the episode. There are some clear shots of status displays showing a 4-nacelle configuration in the Pegasus engineering set, however
And to address the gorilla in the room - Riker visits the Holodeck between scenes in this episode, interacting with a reproduction of the final mission of the NX-01 Enterprise to help him decide what to do, as seen in the final episode of Enterprise.
As Moore joked, this episode treads some well-worn Trek tropes - beyond Picard facing off against a rogue officer, there’s a race against time (and the Romulans) to secure a valuable item, and there’s a secret from a character’s past that causes stress. This episode could have been a disaster, but thankfully it wasn’t.
There’s a lot of elements that work together to make it work - the three principal actors here, Patrick Stewart, Jonathan Frakes and Terry O’Quinn are on top of their games. Frakes especially shines, veering between discomfort, frustration and anger when Riker is interacting with Pressman, and his attempts to give Picard as much information as he can show a conflicted nature incredibly well. Similarly, Picard’s increasing frustration and anger are palpable.
The next six words are a lie: I don’t want to nitpick, but: there are some niggly issues with this episode, mostly around the conclusion. It’s very pat that Riker decides to come clean like five minutes from the end of the episode, when the Enterprise is trapped and the Mcguffin he and Pressman retrieved can save the day. And the idea that the Enterprise is in danger because the Romulans blasted the cave entrance shut doesn’t feel particularly perilous. Like, they’re not going to run out of food or air any time soon, and Data and Geordi are on the ship, so they could probably find a solution in a couple of days. It’s a very convenient way to end the episode.
That conclusion is, as @mike said a great example of how the Enterprise-D command crew have come together. There’s enough trust and respect between them to know that Picard is right and Pressman is wrong. It’s a lot stronger from a character arc point of view than a structural one.
Also, its worth noting that the effects shots for the Enterprise entering the asteroid, the lighting when it’s flying through the cave and the shots of the Pegasus stuck in the rock are all great.
What;s interesting in the light of Discovery’s early episodes is contrasting Riker with Michael Burnham, and Picard and Pressman with Georgiou and Lorca. Riker defended Pressman when he was basically fresh out of the academy, and with 12 years of hindsight he’d have sided with the mutineers. Notably, 7 of those 12 years were on the Enterprise, becoming a family of sorts.
Burnham is in a similar position to Riker in terms of the length of time she’s served on the Shenzhou, and her mutiny is an attempt of sorts to keep that family that she’s cultivated safe. Contrast that to Riker lamenting the death of the Pegasus crew, and Pressman saying that he knew them a lot longer than he did…
It’s also interesting to see what’s happened after their mutinies. Riker defended Pressman, a morally compromised officer, and eventually wound up on the Enterprise, serving alongside the far more virtuous Picard. Burnham mutinied against Captain Georgiou, who was clearly a mother figure/very close friend, and wound up serving under the morally compromised Gabriel Lorca.