ByBecky Storey, writer at
Writer of articles on controversial topics; Mental Health, Women's Issues and less anxiety inducing subjects like Superheros and Sitcoms.
Becky Storey

Toby Flenderson appeared throughout all nince seasons of (US) as the hapless Human Resources Representative for Dunder-Mifflin's Scranton Branch. He was the butt of all of Manager Michael Scott's jokes and his nemesis for years — even if it was a one-sided hatred.

Toby is a somewhat awkward man who followed the girl of his dreams into a dead-end job, who then divorced him anyway and left him with a daughter he struggles to connect with. He fell in love with Pam, then had to spend years watching from the sidelines as her relationship with Jim blossomed. Toby was also hated endlessly by Michael, and then by both Jim and Andy when they were in the temporary position of manager. It's fair to say he didn't have it easy, enough so to snap and turn to a life of crime.

In Season 6 we first learn of the "Scranton Strangler," who is terrorizing the small town of Scranton and committing serial murders. In Season 7, the strangler is caught after a long car chase and police stand off. Later in the series we learn that Toby has been selected to sit on the jury in the court trial of the Scranton Strangler. Finally, in Season 9, Toby reveals that he believes the man they found guilty and sent to death row was in fact innocent. After revealing that the person they sent down was George Howard Skub, Toby begins to battle with his intense guilt and ultimately chooses to visit the man in prison. The camera's weren't allowed into the prison, but he returned having been attacked and strangled, apparently confirming that the right man was caught. However, there's more than meets the eye in this story.

Let's Get Down To The Nitty Gritty: The Evidence

The Pam Problem

Toby Flenderson openly had feelings for Pam, the receptionist, who never had eyes for him. When Toby first learns that Pam is single and ready to start dating, he plans to woo her and get her to go on a date with him. However, Toby being, well, Toby, he gets nervous and fails to ask her. While Pam has always shown a softness for Toby, she clearly never felt quite the same as he did. Then, as if matters couldn't get worse, poor Toby had to watch while the girl he wanted fell in love with someone else.

In the Season 4 episode "Dunder-Mifflin Infinity," Toby sends out an email to the entire office explaining that PDA is not appropriate. This was entirely aimed at Jim and Pam, who were now madly in love but keeping it a secret from the other employees. Eventually, Toby outs their relationship, very clearly jealously. Later in the season, Toby is laughing with Jim and Pam when he awkwardly puts his hand on her leg. The entire room noticed. Suddenly, Toby announces that he will be moving to Costa Rica, runs out of the office and hops the fence.

Toby returns from Costa Rica early after having injured himself badly in a zip line accident, only to learn that Pam and Jim are engaged and he's been replaced at work. In Season 6 episode "Niagra," Toby excitedly states, "Looks like this isn't going to happen" when it appears that Jim and Pam won't be getting married after all.

Unfortunately for poor Toby, they do.

Mean Michael

Toby's time in Scranton wasn't made any easier at work. Michael Scott always had it out for him. He was ignored and ridiculed and essentially bullied for years under Michael, and even under the temporary managers, despite never really doing anything wrong. He only ever wanted to do the best he could for his job. Unfortunately, it didn't seem this way to anyone else, making him the least popular employee in the company.

Over the years, Michael said and did some awful things to Toby — too many to list conclusively. Instead, the insults and moments most likely to make a person snap have been listed:

  • There was the very memorable moment when he told Toby that if he had a gun with two bullets and was in an room with Bin Laden and Hitler, he would shoot Toby twice.
  • All the times Michael made it clear that Toby had no one to go home to.
  • All the times he stated that Toby had ruined his own life.
  • And this moment when Michael learned that Toby was back from Costa Rica:

Toby's Troubles

Toby was never really a successful man. He left the seminary to pursue a girl he fell for, followed her to Scranton and fell into a job in HR almost accidentally. She then left him in a painful divorce and his relationship with his only child became estranged.

Toby often has a lot to say but is never allowed to speak his mind. He is so extremely mind mannered that he's never able to truly express himself. This sort of compressed frustration could definitely lead to a person snapping and having to find another way to let out his anger. Costa Rica offered the possibility of a new start for the poor man, but instead it followed the trend of the rest of his life. Within a few days of arriving, Toby broke his neck in a zip line accident and was forced to come home.

This, we believe, was the moment Toby snapped. Upon returning to Scranton, he began to enact his revenge at the beginning of Season 5.

The Car Chase

In S07E08, the whole group at Dunder-Mifflin watch a car chase between the Scranton Strangler and the police on TV in the office, but Toby Flenderson was suspiciously not present for the entire episode. The theory would suggest that Toby was in fact who they were watching on the TV, and at some point managed to get away in time to frame George Howard Skub. Toby was, at the very least, laying low that day, sitting back knowing it was Skub they were in pursuit of.

Scenes from "The viewing Party"
Scenes from "The viewing Party"

The Jury Trial

Later in Season 7, Toby had to take a leave of absence from work because he had been called to sit on a jury in a high profile case. Toby was very clearly excited about this and was unable to keep it secret despite secrecy being required by law. Eventually he revealed it was in fact the trial of the Scranton Strangler. Toby stated that he was pleased that his opinions were going to be valued, but in reality he was most likely excited that his plan had worked. Not only had he gotten away with it, but he had finally done something that people had taken notice of.

The jury found the man on trial guilty and he was sentenced to death row. However, Toby eventually began to feel an intense guilt. He openly confessed to Oscar that he didn't agree that the man they had convicted was guilty. He explained to Nellie that he had been doing his own research on finger printing and was starting to believe that Skub was innocent. This was instead a clear indication of his own guilt setting in, not only had someone else been found guilty, but they were sitting on death row too. Nellie convinced Toby to visit the prison and talk to the man he'd helped to put behind bars. The camera's weren't allowed into the prison, which makes the visit all the more suspicious. When Toby returned after his visit he had been strangled, apparently confirming that the right man had been jailed. However, the theory would suggest that during the visit, Toby actually taunted the man and revealed that he was the real Strangler. It seems pretty appropriate that if Skub was going to lash out then he'd do it by strangling, given that that was the reason he was there.

Look how happy he one is that happy to meet the person they sent to death..
Look how happy he one is that happy to meet the person they sent to death..

Extra Hints and Dropped Comments:

  • Around the time of Toby's appointment to the jury, he began working on a series of novels titled The Flenderson Files. These were crime thriller novels based around death and murder. After the trial, the novels become a pivotal part of Toby's character, drawing attention to his more sinister side.
  • In an exchange with Michael, Toby says that asbestos is the silent killer. Michael responds that Toby is the silent killer. In true Office style Toby looks to the camera and says "you'll see." If that's not a confession I don't know what is.
We see Toby, we see.
We see Toby, we see.
  • There are some serious inconsistencies in Toby's background stories, suggesting he's trying to hide parts of his past. We've heard that he attended several different universities and gained several different degrees, and also that he was training in a seminary for a year. According to Toby, he's attended Penn State, California Coastal College for Psychology and Temple University for Social Work. Seems highly suspect to me.

Conclusion: Toby Flenderson Is Definitely The Scranton Strangler


Do you think Toby is the Scranton Strangler?


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