If You Watch The Office Enough Times, You Can See One Big Twist Coming A Mile Away
You have no idea how high he can fly.
One of the things I've come to really appreciate about The Office is how it set up some of its most interesting stories and character arcs over time, rather than just springing a twist on us in one episode just to change things up. During one of my recent rewatches of the series, I was especially appreciative of the way Season 5 sets up a major twist that plays out later on in the season. I'm talking about when Michael Scott quit his job at Dunder Mifflin.
To be clear, this isn't when he left the company for good to move to Colorado with Holly. Steve Carell's departure from the series happened seasons later. In Season 5, however, his character did what seemed unimaginable at the time, and decided to walk away from Dunder Mifflin. Given how loyal he was to the company up to that point, it seemed impossible that he'd ever leave... but it really didn't come out of nowhere. While the arrival of Charles Miner certainly provided the catalyst for Michael's exit, I think Idris Elba's character was merely the straw that broke the camel's back.
Let's take a look at some of the events earlier in Season 5 that led to Michael's breaking point.
Holly Gets Transferred To Nashua
Watching the series in its original run, I don't know that I could've guessed that Amy Ryan's character would turn out to be "the one" for Michael Scott when she was first introduced. Of course, getting to know her over time, and seeing how their relationship played out, it's easy to see how perfect she was for him from the start.
Michael and Holly's budding romance fell apart within episodes when David Wallace found out about it, and had Holly transferred to the Nashua branch. A harsh reaction on David's part? On the surface, it might appear that way, but in defense of David's evident visions of red flags all around the situation, let's not forget that Michael's last interoffice relationship included him being mixed up in a deposition that could've cost the company millions. So maybe David's cautiousness wasn't completely unwarranted.
The Disappointing Business Trip
Michael seems delighted to have the opportunity to travel to Winnipeg on behalf of the company, but nothing about the trip goes the way he hopes. Not even a one-night-stand with the charming hotel concierge could lift Michael's spirits, and by the end of the trip, he was ranting to David Wallace over the phone about how awful it was, and how mad he was about Holly being transferred. No, I don't think this bummer of a work trip caused Michael to quit, but it certainly was an indication that he wasn't over Holly's departure, and not even a business class flight to Canada was going to fix that.
Toby Returns
"No, God! No, God, please, no! Nooooooo!," are Michael's exact words upon learning that Toby is back from Costa Rica. Again, is that a reason to quit? Nah, but I doubt Toby’s return to the office helped boost morale for Michael. It definitely fits into this timeline.
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Michael’s Moral Dilemma Over Prince Family Paper's Client List
Now, before this episode, we saw Michael go to New York to meet with David, enjoy some takeout and talk about absolutely nothing, while David tried to glean some insights into how Michael was keeping his branch profitable. That seemed to indicate that maybe things were looking up for Michael at work. And then came "Prince Family Paper," the episode where Michael is tasked with gathering intel about a business that was providing a bit of competition for Dunder Mifflin.
It was one thing to devise a plan to secure the information, but it's clearly another for Michael to turn over the client list he obtained, when he considered what it might do to this local family-owned business. It takes Dwight physically prying the list out of Michael's hands, in fact. So it's not hard to imagine that the ordeal weighed on him, or at the very least, made him feel not-so-good about his job.
Michael’s Golden Ticket Idea Backfiring
Michael Scott wasn’t always the problem in The Office. In fact, he sometimes had a good idea. However, his "Golden Ticket" idea was a rollercoaster ride, where it seemed like the promotion backfired and cost the company a lot of money, only for it to turn out to be a good thing. So it all worked out, right? Wrong. Michael's efforts to deflect blame, then claim credit made the whole thing really messy, which results in David Wallace storming out of the Scranton office.
We might also factor in David's frustrations after Dwight's safety training shenanigans during "Stress Relief" – one of The Office’s best episodes – a few episodes earlier as part of the mounting tension here. Is it any surprise that David would bring in help in managing the branch?
And Then, Charles Miner
That brings us to "New Boss," which introduces Idris Elba's Charles Miner, who immediately rains on Michael's 15th anniversary party-planning parade with his cost-saving efforts and zero-tolerance for nonsense. To make matters worse, when Michael tries to contact David to complain about the situation, his call is forwarded to Charles’ line. I think that's truly the last straw. But, factoring in all of the other events, it’s easy to see the look on Michael’s face as David tries to placate him, and know that even a party and some figs aren't going to be enough to make him want to stay at Dunder Mifflin.
It might not be quite as easy to put together a similar list for why Pam decided to quit alongside Michael. Sure, she’d been restless with her job, especially when we factor in her return from New York, and being tired of dealing with the new copier. Still, her spur-of-the-moment choice to abandon her job did lead to her getting out from behind the reception desk, as she eventually returned to DM as a salesperson (and then sneakily navigated her way into an office administrator role later on). So, I guess it wasn’t one of the worst decisions an Office character ever made.
The Office wasn't always perfect with its continuity (and it certainly wasn’t the only show guilty of that, either). Watch a series enough times, and you may notice random things that don't line up with later events. However, The Office was consistent where it counted, which is why most of us likely give it a pass for things like Meredith mentioning having a second child, whom we never actually saw or heard about again.

Kelly put her life-long love of movies, TV and books to greater use when she joined CinemaBlend as a freelance TV news writer in 2006, and went on to serve as the site’s TV Editor before joining the staff full-time in 2011 and moving over to other roles at the site. At present, she’s an Assistant Managing Editor who spends much of her time brainstorming and editing features, analyzing site data, working with writers and editors on content planning and the workflow, and (of course) continuing to obsess over the best movies and TV shows (those that already exist, and the many on the way). She graduated from SUNY Cortland with BA in Communication Studies and a minor in Cinema Studies. When she isn't working, she's probably thinking about work, or reading (or listening to a book), and making sure her cats are living their absolute best feline lives.
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