Michael accidentally gives Blue Cross a 50% discount, putting Jim's job in Jeopardy since they were his client. He takes advantage of Dwight's loyalty to him by convincing him to take the blame for the discount, only to then betray Dwight when the CFO of the company congratulates him on the initiative because Blue Cross decided make Dunder Mifflin their sole office supplier.
You might say that this serves as comeuppance for Dwight's attempt at usurping Michael a couple seasons earlier, but Dwight had already atoned for that by agreeing to do Michael's laundry for some length of time. This is fucked up. Michael almost got two people fired because of his inability to own up to his ineptitude and then selfishly tries to steal the rewards of an accidental success.
Michael learns that Stanley is cheating on his wife after feeling left out of some meaningless interoffice gossip, so he decides to tell everybody about it to make himself the center of attention, not realizing that he's putting Stanley's marriage at risk. Then he creates a series of false rumors about the rest of his staff to distract from the truth about Stanley.
Jim & Pam - He tells everyone they're secretly expecting a baby. They actually were. Not that big a deal.Jim & Pam decide to reveal the pregnancy to cover for Stanley when the office demands to know which rumor is actually true.
Kelly - He tells everyone she has an eating disorder. This is fucked up because Kelly clearly does have self-image issues, but Michael is too stupid to realize how damaging it could potentially be to draw attention to someone going through that in that way. She escapes the episode unaffected though.
Kevin - That there's a smaller person inside of him working him with controls. This is simultaneously the most clever and the meanest fat joke I've ever heard.
Erin - That she's a terrible worker, nobody likes her, and she's on the verge of getting fired. This is the second time he's made this joke about her and he literally learned nothing about why it's a bad idea since he did the same thing to Pam in the pilot episode and saw how distraught she was over it. This is not the last time he'll be a total dick to the nicest person in the office, either.
Angela - That she's dating an old rich guy. This is nothing.
Oscar - That he's the voice of the Taco Bell dog. He skipped right over homophobic and went straight to racist. Amazing.
Andy - That he's gay. This is interesting because the show's writers were teasing the questioning nature of Andy's sexuality since his first appearance (from having him offer to share a sleeping bag with Jim in Stamford to the extremely low hanging fruit of having him star in a musical in a late season episode) and some of the other characters have picked up on it over the years, but they knew better than to make a fuss about it. Michael, on the other hand, almost got the company sued for outing Oscar in season 3, so you'd think he might have learned something about why that's a fucked up thing to do to someone, but I guess not.
Toby - That he's still a virgin in spite of the fact he has a daughter. Michael hates Toby, so this is nothing but plain silly.
But here's the cherry on top: Michael eventually manages to tip off Stanley's wife that he's having an affair anyway, resulting in the end of their marriage. This is an astounding series of bad decisions all made in a very short time span, many of which are repeat offenses.
Years back, Michael pledged to a group of school kids that he'd pay for their college tuition if they all graduated high school. The story made headlines in the local paper.
WHY? Why would he do that?
Michael was trying to inspire them because they were at risk of being dropouts. And it worked - most of them were on track to graduate.
OK, but you're not rich, Michael. You can't afford to send 30 kids to college.
Michael thought he would be rich by the time they were ready to graduate.
Then we get to watch him walk back on that promise and we get to watch 30 kids be disappointed.
I get frustrated just thinking about this. There is nothing funny about this episode. It is the single most difficult to watch episode of a sitcom I have ever seen.
The writing of this show was very uneven over the years and it routinely crossed lines in the wrong places because it traded on making the audience uncomfortable. That's absolutely the charm of the show, but it suffered from having to up the ante season after season, I guess. Anyone else have any thoughts about Michael's fuck ups?