Michael Scott hates Toby Flenderson. This is not a mystery. This is not a subplot. This is a foundational truth of The Office that never wavers across nine seasons.
The reason is simple. Toby Flenderson is an HR Rep.
That’s it. That’s the whole thing. Everything else is just Michael Scott being Michael Scott.
The Reasons Michael Scott Hates Toby Flenderson
- Toby Flenderson is an HR Rep.
Also, per Michael Scott, the only thing worse than one HR Rep is 2 HR Reps. That’s, of course, unless it’s an HR Rep with an ass that doesn’t quit ~~ Miss Holly Flax (Amy Ryan).
Well, That’s It. One Reason… Toby is an HR Rep
Toby Flenderson is actually a pretty nice guy, except he’s an HR Rep. While clear efforts are made by Toby to enforce the corporate policies of Dunder Mifflin, he is pretty accommodating overall.
There are actually more reasons Michael Scott should NOT hate Toby Flenderson…
Basically, Toby Flenderson is a pleasant HR Rep box checker.
For instance, when Michael threatens to withhold sex with Jan to get a raise at Dunder Mifflin. Instead of reacting as a stereotypical HR Rep, Toby is excited to potentially be part of a lawsuit that HR Reps have never seen before.
On another occasion, Toby often gets excited when he gets to use “new forms.” For instance, when Dwight Schrute (Rainn Wilson) is interim manager & shoots a gun in the office. Other than Dwight not becoming manager, he really doesn’t get into trouble… but Toby got to use a form he never used before.
Related: Chili’s is the New Golf Course & The Office Proved It
Finally, the best example of this, in a nutshell, is when Sabre acquired Dunder Mifflin. A banker was sent in… The banker asked Toby a series of questions to assess the risk of acquiring Dunder Mifflin. Each question is answered to set Dunder Mifflin up for success (after Toby Flenderson sees flashbacks of what actually has gone on at The Office).
Toby Watches Out for Michael: Examples…
Somehow, Michael missed making a hotel reservation before traveling to Niagara Falls for Jim & Pam’s wedding. Michael arrives to find himself without a reservation at check-in & no room at the Inn.
He attempts to stay with Dwight, but Dwight wants to get laid & does not have a roommate. Dwight does end up having intercourse with Pam’s BFF, Isabela.
Toby overhears Michael’s conundrum of not having accommodations & offers to let Michael stay in his room, as his room has 2 beds.
Michael not-so-politely declines… “You will be sleeping alone for the rest of your life, so you should just get used to it.”
Then, back when Scranton absorbed the Stamford branch, including their employees, the Scranton employees learned about the Black transfer from Stamford’s time in the clink.
Martin Nash (Wayne Wilderson) explains what he did to end up in prison & this confuses Kevin Malone (Brian Baumgartner) as he thinks this sounds like what he does at Dunder Mifflin.
Kevin had Martin explain to him 3 times what he got arrested for & he’s pretty sure what Martin described all 3 times is what he does in accounting every day at work.
He is less worried after Martin sheds some light on how being in prison was. Kevin was most excited about “Outdoors Time.” The others were also interested in “Outdoors Time” & asked Michael why they didn’t get “Outdoors Time.”
As Martin went on about what he described as a not-that-bad experience in prison, the employees wondered out loud if prison is better than Dunder Mifflin.
This angers Michael Scott.
He locks his employees in the conference room to teach them a lesson. Somehow, Toby was not locked in with the others & was at his desk when he received a phone call from the others asking for help to get them out.
Toby asks Michael what’s going on. He explains. Toby tells Michael that the employees are simply giving him a hard time. He reassures Michael that the employees do like working at Dunder Mifflin & it’s a great place to work.
Michael releases the employees from “Conference Room Prison” & all is well again in The Office.
Holly Flax on The Office Replaces Toby When He Goes to Costa Rica
Finally, what if Toby never went to Costa Rica? He would have never been replaced by Holly Flax, the inevitable love of Michael Scott’s life.
Some say there is an exception to every rule. In this case, Michael Scott hates HR Reps.
Toby decides to move to Costa Rica, therefore he needs to be replaced. We all know by now what is worse than 1 HR Rep ~~ it’s 2 HR Reps.
Well, that lasted a day. Toby trained the new HR Rep, Holly Flax, within a day & took part in his exit interview with Michael. Michael gave him a rock (with a note stating to “Suck on This.”) to apparently rub in his hatred just a bit more.
Now with Holly Flax in the room (with an ass that does not quit, per Michael), he has to step things up with his watch. Yes, to make a good impression on Holly, he gave Toby Flenderson his watch.
Michael Scott Hates Toby & Sometimes David Wallace
David Wallace (Andy Buckley) relocating Holly to Nashwua after he realized she & Michael were dating was a surprise. Like Toby Flenderson, David Wallace also watched out for Michael.
Holly Flax relocates. Toby is back. Michael wants to fire Toby. David Wallace will not let Michael fire Toby without cause. Michael would like to fire Toby beCAUSE he hates him.
Not only has David Wallace relocated the love of Michael’s life to Nashua & won’t let him fire Toby upon his return to Scranton, but he then sends Michael to Canada.
While Michael totally gets with the concierge lady at his hotel, she’s no Holly. At least Andy Bernard & Oscar had a good time in Canada.
THE Reason Fans Can Hate Toby Flenderson
Perhaps Toby should have acted on his ongoing crush on Pam. They are both boring & are partial to living in Scranton. He totally had a crush on her throughout the entire series & was at best passive-aggressive in conveying his crush to Pam.
Remember when Pam Beesley (Jenna Fischer) & Jim Halpert (John Krasinski) first got together?… They were proactive in inquiring to fill out an “Office Relationship Form.” Toby would not have it. “Office Relationship Forms” are only needed when things are serious. Pam & Jim let him know that things were serious. Toby told them that they could hold off, for now, to see how things go.
Toby then distributes a form about PDA in the office. Pam & Jim smiled a lot & pulled office pranks. Not so much PDA’s. Passive-aggressive Toby Flenderson…
On Toby’s last day, however, Pam did admit that she thought Toby was cute.
Toby & Pam should have totally ended up together & Jim would have gone on the 3-month Athlead trip with Darryl. Maybe he could have married Karen. She was for sure open to not staying in Scranton
An Exception in Human Resources: Toby’s Last Day Brings Holly
Without Toby, Toby would not be able to leave to go to Costa Rica. Ergo, most likely, Holly Flax would not have been brought to Scranton to replace Toby on The Office.
Michael Scott instantly fell in love with Toby’s replacement, Holly Flax. They dated & all was good until David Wallace decided to relocate Holly back to Nashua.
They tried a long-distance relationship that expired by the time Darryl Philbin (Craig Robinson) drove Michael & Holly with her stuff to Nashua. Somehow, the couple didn’t realize how far Scranton was from Nashwua & how much time would be spent on the road if they continued their relationship.
Then Toby comes back. I think this is the only time loyal fans of The Office (& David Wallace) hate David Wallace. David Wallace relocated the love of Michael’s life, then brought back Toby.
Michael & Holly come in contact again at a company picnic, where they have been chosen by David Wallace to put on a skit. The skit itself ends up putting David Wallace into a predicament as Michael & Holly disclose that the Buffalo branch of Dunder Mifflin is closing. The Buffalo branch employees (& their families) attending the company picnic did not know this. Now David Wallace has to deal with them.
Karma?? Maybe David Wallace shouldn’t have relocated Holly to Nashua…
Regardless, Holly ends up back in Scranton & she & Michael do get back together. He proposes & they relocate to Colorado to be close to her aging parents & to begin their life together… & Michael Scott still hates Toby.
Without Toby leaving for Costa Rica, there is no Holly Flax. Without Holly Flax, there is no love of Michael Scott’s life. So in a way, Michael Scott owes everything to the man he hates most.
He would never admit that. Ever.
It’s not my first day watching The Office, & it isn’t yours either. Which Michael HATING Toby moment is your favorite?
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