To “break bad” is to go wrong or turn to crime, much like Walter White did in Breaking Bad, going from mild-mannered teacher to commanding drug kingpin. Many characters in TV have the capacity to go bad, but none more so than the characters of The Office, many of whom have committed some pretty terrible crimes.
Many Office characters blatantly do their bad deeds out in the open, such as Dwight keeping weapons around the office in case of intruders and Phyllis calling in Bob Vance when she feels threatened. The bad behavior of these characters only really serves to make the audience like them more, as it reminds us that they are imperfect people.
Dwight is often the smartest person in the room but he sometimes puts his coworkers in danger, such as when he sets a fire to teach them about fire safety. A popular fan theory was that Dwight was the Scranton Strangler, as he has detailed knowledge about the human body and knows combat techniques, becoming a black belt in karate in the final season of the show.
Dwight cut the face off the CPR dummy, emulating a scene from the Hannibal Lecter movies, pretended to be a police officer to escort Jim and Pam to the hospital, and kills several animals over the course of the show: Angela’s cat Sprinkles, a goose at Christmas, and several horses. Really the only thing preventing Dwight from doing crime is his intense hatred of crime.
Fans speculated on who could be the Scranton Strangler until the strangler was caught, and a popular theory was that the Strangler was Toby. The mild-mannered HR rep could snap at any time, thanks to his treatment by Michael and his ex-wife, and is sometimes found muttering things to himself like “you’ll see” when Michael shoots down his ideas. He is also trained in combat, as he taught a class about self-defense.
Toby seems unlikely to do a crime, as he was a member of the seminary (a Christian theological school), but he did drop out to pursue a relationship with his now ex-wife, Cathy. Toby also drops or bends the rules occasionally if they suit him, such as when he serves alcohol at a Christmas party and refusing to let Pam and Jim sign a relationship disclosure, so his morals are a little loose.
All of the Dunder Mifflin accountants have the capacity to break bad, especially Angela, who called a hit on Oscar for cheating with her husband and was willing to let Trevor break Oscar’s knees. Angela is a natural leader as the head of accounting, and sometimes takes measures to remind people of her power, encouraging Dwight to revolt against Michael and take his job, and bullying Phyllis and Pam as head of the party planning committee.
Angela is also one of the most secretive characters, often doing things in the shadows rather than being upfront about her actions, such as cheating on Andy with Dwight, and secretly coming up with jokes for Pam’s caption contest.
Fans of The Office have often speculated that Kevin embezzled money from Dunder Mifflin, as it was implausible that he would buy an entire bar after getting fired from the office. Kevin invented a new number, the Keleven, which could be said alludes to him stealing money from the company with his questionable accounting practices.
Kevin’s gambling addiction also leads him into trouble a few times throughout the series, and Michael goes to him for advice on rigged fights, which Kevin might know about if he were ever to turn to crime. Kevin has mixed results when keeping secrets, but did manage to keep Oscar’s secret about the state senator, so perhaps an undercover life of crime isn’t too unfeasible for Kevin.
Michael did actually break the law several times during the series, such as when he hit Meredith with his car and organized an illegal casino night in the warehouse. Michael also did drugs and almost got busted — even if the only one who cared about that was Dwight — and framed Toby for having drugs but got out of it when the police actually turned up. Michael also sometimes romanticizes crime, pretending to be Agent Michael Scarn at improv and in his movie.
Michael would do anything to be the center of attention, and would definitely try to spin the perception of the crime in his favor. It is unlikely that Michael would do an outright crime unless it was by accident, but if one of his friends asked him to participate, it is also unlikely that he would say no.
Much like Michael, Ryan broke the law several times in the show, including fraud with Dunder Mifflin Infinity, getting involved with drugs while living in New York, and child abandonment when he left his baby Drake to elope with Kelly.
Although some fans feel that Ryan’s drug abuse makes no sense in the midst of the show, Ryan getting swept up in the high-stakes life of corporate America is a fun side plot that enhances his character and makes Michael extremely jealous. As Michael’s perceived protege, Ryan reaches heights that Michael doesn’t, giving them plenty of fun, confrontational scenes.
In earlier seasons, Andy might not have been a character that would commit a crime, as he seemed responsible enough during work hours and just wanted to be liked, albeit not as much as Michael. However, Andy has an anger problem that lands him in trouble several times, and he got Dwight fired by cozying up to the boss.
Andy has some of the funniest quotes in the series, and in later seasons, could undoubtedly do something attention-grabbing like a crime, as long as it gets him fame. In addition, Andy technically wasn’t insured or licensed to sail the Bernard family boat but he did it anyway, so there is no telling what he could get away with.
State Senator Robert Lipton
State senator Lipton has been proven to be untrustworthy and a liar, using Angela and Oscar to advance his political career. His pleasant and often humorous exterior could hide a nasty streak, covering up crimes easily with his perceived personality and abuse of power (the limited amount of power that a state senator would wield).
If he had kept Angela on his side, and not pushed her away, they could have made a very powerful couple, as Angela has proved to be less than moral in her own life. Angela embraced the life of a state senator’s wife, so the couple could have got away with much more than just keeping a few affairs secret.
Robert California absolutely has a shady past, as California is not even his real name. Robert has extraordinary power over other people, convincing the Scranton branch to make him manager, unnerving Dwight with just a look, and convincing Sabre CEO, Jo Bennett, to give him her job. What else could he convince someone to do if he were in the mood to commit a crime?
In many ways, Robert was actually a good CEO and had no qualms about knowingly running a company that sold subpar products. He also stokes trouble quite a lot, telling a scary story at the Halloween party that shocks everyone, and often playing mind games with Andy and Nellie.
Creed is the wildcard of the office, which is exactly why fans love him. The list of crimes that Creed commits on camera is extensive. Among other things, he got Debbie Brown fired for a mistake he made, fled the scene when he thought the office suspected him of murder, appeared at the Halloween party covered in blood and stated “that [was] really good timing,” stole poker chips from casino night, swiped a laminating machine from the sheriff’s office, and stole blood from the blood drive.
There are so many reasons why Creed should have been the boss, but it is understandable that his long list of known and unknown crimes would disqualify him from candidacy.