The BEST: The Office

“The BEST” series features writers considering what elements in our culture still inspire us to live better and seeks to share what we find that might still be described as “the best that has been thought and said.” Click here to read about “The BEST” and to see the index of all columns in this series.

Summary
The Office (2005–2013) is a mockumentary sitcom following the daily lives of employees at the Scranton branch of the fictional Dunder Mifflin paper company. Through awkward humor and heartfelt moments, it explores workplace relationships, leadership, and the search for meaning in ordinary jobs.

Its central figure for much of the run is regional manager Michael Scott, who is neither cruel nor a mastermind. He’s a lonely, attention-hungry man who desperately wants to be liked, and just as desperately wants to believe that his impulses are generous. He often confuses being good with being seen as good, and that confusion isn’t incidental; it is his defining weakness. He reaches for big gestures as a shortcut to love, and he cannot reliably tell the difference between a moral act and a flattering story about himself.

“Scott’s Tots” (Season 6, Episode 12) is the quintessential example of this dynamic. A decade before the episode unfolds, Michael visited a local school and promised a class of third graders that if they graduated high school, he would pay their college tuition. Now that the students are seniors, the school has built a whole narrative around the promise and invited him back for a celebration. Michael must confront the reality that he never had the money, never had a plan, and never understood what he was doing when he made that pledge.

Why this is The BEST
Many people think of The Office as comfort viewing, but it’s built on a strange ingredient: discomfort. The show’s comic engine is often what we now casually call “cringe”—that tightening-in-the-chest feeling when someone’s neediness or self-delusion pushes them into behavior that is obviously wrong, and we can see the consequences coming before they do. “Scott’s Tots” is a modern morality tale: someone thinks he’s doing something good, but what’s really driving him is a selfish need for admiration, gratitude, the pleasure of being a hero. Other people then build their lives around that promise, and when it collapses, they’re the ones who absorb the pain.

Cringe stories evoke strong discomfort or moral unease not because the characters are cartoon villains, but because they’re trying to do the right thing (or persuading themselves they are) and do it terribly: awkwardly, irresponsibly, or in ethically compromised ways. They force us to watch as intention, action, and consequence unravel.

The episode also raises a harder question than “Is Michael good or bad?” The viewer must decide if a good outcome can excuse the bad choice that produced it. It’s plausible that Michael’s promise, however irresponsible, motivated these students to work harder, aim higher, and imagine college as possible. The episode won’t let that good outcome become redemption. Michael didn’t make a calculated sacrifice to help them. He made a grand promise for selfish reasons. If any benefit comes, it’s accidental.

That’s where the concept of moral luck helps. “Moral luck” is the unsettling fact that we often judge people not only by what they chose, but by how things turned out. In “Scott’s Tots,” Michael doesn’t really receive “good luck”: he suffers exactly the humiliation he deserves. The more subtle temptation is ours. If the students strive and succeed based on his false promises, we may soften our judgment of Michael. The episode is built to resist that temptation. Responsibility is what you chose and why you chose it, not what history might redeem.

Cringe isn’t only a modern plot device. The Torah contains narratives that do something similar: they make us recoil, not because we’re meant to sneer at villains, but because we’re watching human beings reach toward something “right” and get there through something terribly wrong.

Lot’s story (Genesis 19) is a striking example. Lot seems drawn to Abraham’s ethic of hospitality and protection of guests, but in Sodom his attempted “righteousness” becomes grotesque: he offers his daughters to the mob to spare his visitors. Later, his daughters seek to preserve their family line by intoxicating their father and becoming pregnant by him. Both stories leave the reader with the same kind of moral recoil that “Scott’s Tots” produces: we can see what they think they’re trying to do, but we can’t accept what they did.

That morally tangled origin leads to the nation of Moab. Later, in the time of Ruth (a Moabite), intention, action, and outcome lined up properly in a story that could have gone otherwise (Ruth 3–4). There is risk and vulnerability, but no illicit seduction and no abandonment of the vulnerable: Ruth makes her request directly, Boaz responds with restraint, and the relationship is confirmed openly (4:1–12). From that line emerge David and the Davidic dynasty.

Jewish law directly confronts this tension between intention and action in the laws of yibbum, where intention is not a decorative “nice to have,” but central to whether the act is a mitzva or a transgression. The Mishnah says explicitly that halitza came to take precedence over yibbum when people were no longer trusted to do yibbum for the sake of the mitzva (Bekhorot 1:7). The Gemara records Abba Shaul’s claim that yibbum done for beauty, desire, or gain, instead of to fulfill the mitzva of levirate marriage, is akin to forbidden relations (Yevamot 39b).

All of this brings us back to Michael Scott, whose problem is not only that outcomes don’t match intentions, but that he cannot be trusted to read his own intentions accurately in the first place. “Scott’s Tots” separates categories that often blend together: what I meant, what I did, and what happened afterward. It refuses to let accidental benefits (if any) turn irresponsibility into virtue, and it refuses to let a sympathetic personality become a moral exemption.

If there is something here that can make us live better, it’s not a rule about never making big promises or never taking risks. It’s the demand to be honest about motives before we act, and to measure responsibility by whether we had the right to make the choice we made. We should distrust grand gestures that cost us little but bind others. Help others; do not try to be seen helping. We can build habits of accountability: inviting pushback, putting commitments in realistic terms, making sure the vulnerable aren’t paying for our self-image and esteem. Outcomes still matter, and we should certainly be grateful when good emerges from a mess. But if we don’t want to be Lot, Lot’s daughters, or even Michael Scott, we can’t rely on history to clean up after us. We have to keep intention and action in view even when the ending is uncertain.

David Curwin, a technical writer in the software industry, publishes widely on Bible, Jewish thought and philosophy, and the Hebrew language.