“The Office” Season 4 is full of some of the best content the iconic NBC smash-hit comedy ever produced. Episodes like “Dinner Party” and Fun Run are among the best episodes of the entire show; Pam and Jim finally hook up early in the season and nearly get engaged by the end; and Ryan has his meteoric rise before flaming out and ending up behind bars.

But despite the string of top-notch entertainment, there are a few controversial and confusing moments here and there — including a Michael Scott scene in the episode “The Deposition.” The Dunder Mifflin Scranton boss is caught between his vengeful girlfriend, Jan (Melora Hardin), and the top brass who are responsible for her recent termination from the company. Despite the natural pressure to side with his girlfriend, when push comes to shove, he sides with the latter, defending them against Jan’s viscous, disparaging attacks. As the episode ends and Michael is asked if his company exhibits a pattern of disrespect toward its employees, he says, “Absolutely not,” defending the organization and tanking Jan’s case in the process.

The question is, why? Why is Michael willing to throw his girlfriend under the bus for his employer? The answer is complicated, but the sweet and simple version is that we simply don’t know. Michael himself literally says, as the episode ends, “Why did I do it? I don’t know.” However, we do get a series of breadcrumbs throughout the episode that hint at the enigmatic boss’s deeper motivations, starting with his next line: “You expect to get screwed by your company. You never expect to get screwed by your girlfriend.” Let’s dig into the details behind Michael’s controversial call in “The Deposition” and what might have driven him to make it.

“The Deposition” is the eighth episode in Season 4’s truncated 14-episode run. (The season suffered from disrupted production and has a number of two-parters, which makes the total number of episodes a bit difficult to count.) It primarily follows Michael and Jan as they head to the Dunder Mifflin corporate headquarters in New York City for the latter’s deposition. This is part of Jan’s attempt to wring $4 million dollars out of the company (although talking specific numbers is tacky) as part of a wrongful termination settlement.

We see Jan groom Michael with rehearsed answers, but once he’s in the chair being questioned, it doesn’t take him long to go off script. The momentum shifts back and forth as the prosecution and defense lawyers grill the helpless lover and employee who has found themselves caught in the crossfire. The topless picture of Jan surfaces at one point, pushing her to reveal Michael’s personal diary to bolster her case. In the end, Michael is forced to choose sides, and he opts to state that Dunder Mifflin is a good company that doesn’t prey on its employees.

Oh, yeah — while all that is happening, Pam tries to shut up the smack-talking Kelly by training Jim to become a ping-pong master who can defeat Darryl. But that side story is really just fluff while the real drama unfolds in the Big Apple.

The reason Michael decides to turn on Jan is never made clear. However, a few things stand out that help point us in the right direction. One of these is his diary; while Jan is clearly pushed to reveal Michael’s personal memoirs after a vacation picture is revealed (which is Michael’s own fault), that doesn’t change the fact that she is betraying her boyfriend and revealing his most secret inner thoughts to an audience that includes his arch-nemesis, Toby. The episode also reveals that Jan gave Michael consistently poor performance reviews while she was his boss.

In addition to these obvious points, there’s a lot of subtext here. The most likely motivation lies in Michael’s oft-buried, nearly nonexistent intuition. Despite being told moments before that David Wallace never seriously considered him to take Jan’s place after she was fired, Michael refuses to turn on the company that has taken such good care of him over the years. Also, consider Season 5 Episode 5, “Employee Transfer.” When Michael’s then-girlfriend Holly (Amy Ryan) says they should break up, Michael’s panicked response is that he’ll go back to Jan, even though he hates her.

Deep down, Michael knows that Jan is an abusive girlfriend. He also knows that, despite specific decisions made at certain moments, Dunder Mifflin is a loyal employer run by reasonable people, as is proved by David Wallace’s sincere apology at the end of the episode. Even in that scene, Michael’s intuition shines again when he says, “Hey David, I think you’re a nice guy, too,” even though David didn’t actually say those words. While we’ll never have a clear answer, it seems safe to assume that at least part of Michael’s reason for going against Jan in the deposition was because he subconsciously saw that, between her and Dunder Mifflin, his employer had been the more loyal and trustworthy element in his life.

Despite his loyalty to Dunder Mifflin, Michael does eventually leave the company — not once, but twice, and both times it happens on his terms. In Season 5 Episode 18, “New Boss,” Michael quits due to changes at work (more on that in a minute) and heads off to start his own paper company to compete with his former employer. This short-lived experiment nearly ends in disaster, but before the end of the season, Michael manages to leverage his new business into reclaiming his old job.

From there, Scott hangs tight through Season 6. It isn’t until halfway through Season 7 that Michael’s ex-girlfriend, Holly Flax, appears back on the scene after being transferred to another office in Season 5. This prompts him to woo her, date her, propose to her, and then permanently pack his bags and head for a happily ever after spent living in the Rockies with his gal.

So, did Michael’s departure hurt “The Office?” Well, the honest answer is yes — and no. On the one hand, Michael Scott is an integral part of the show. Most of the characters play heavily off of his abrasive, off-the-cuff management style, and when you remove that, it becomes harder for the show to maintain its cohesiveness. Season 8 has its rough points despite a few fun strings of episodes, and for a minute there, it feels like the show really is going downhill.

However, the folks in charge of “The Office” managed to turn things around in Season 9 by pulling out all of the stops as part of the show’s final season. They wrap up stories and play heavily into the fictional in-story documentary aspect, resurrecting interest in the Scranton office crew for one more hurrah before wrapping things up with a finale that stands as one of the show’s top-rated episodes.

The first time Michael quits his job, he’s replaced by Charles Miner (Idris Elba). The new boss who replaces Jan comes into Scranton with guns a’blazing, prompting Michael to quit and compete with his employer. This leaves Miner filling the role of boots-on-the-ground manager in Scranton as he desperately tries and fails to replace Michael. In the end, he and David Wallace are forced to compromise by buying out Michael’s company and restoring him to his previous position for another couple of years.

Eventually, Michael does leave Scranton for good, but that doesn’t take place until Season 7, when he moves to Boulder, Colorado, to live with Holly. When that happens, he’s initially replaced by the equally (though different) enigmatic Deangelo Vickers, played by Will Ferrel. While Ferrel was described as a “palate cleanser” for the writing room, his character quickly moves on, as do the litany of other candidates in the two-part Season 7 finale, “Search Committee.”

It isn’t until the opening moments of Season 8 that it is revealed James Spader’s Robert California has been selected as the new head honcho of Dunder Mifflin Scranton. Even then, California’s time in Michael’s place is short-lived. The ambitious and disturbing leader takes one look around his new job before heading off to convince his new boss, Jo Bennet (Kathy Bates), to give him her own job as CEO. Once that transfer of power takes place, California chooses Andy Bernard as the official Michael Scott replacement.