Michael Scott from The Office is one of the most recognizable bosses from any piece of mediab ever. Whether you love his character or hated him, there’s no denying that he helped make the series as successful as it was. His interactions with other characters and his awkward behavior were both hilarious and cringe-worthy.
While Michael wanted everyone to like him more than anything, he also wasn’t always very nice. He had quite a few rivals and even enemies throughout the course of the nine seasons of the show.
Oscar Martinez
Oscar was one of the employees who was most annoyed by Michael. He knew that Michael wasn’t very smart and that he was an incompetent boss, so he didn’t like having to put up with all of his antics.
It’s hard to blame Oscar for this, especially after the way Michael acted when he found out Oscar was gay. Michael was also aware of how little Oscar respected him, and he knew that Oscar thought he was kind of stupid.
Darryl Philbin
Darryl Philbin is one of the employees that Michael treated the worst in many ways. While he was usually not outright mean to him the same way he was to some others, he never respected him. Darryl was a hard worker who had many ideas for the company, but Michael never took him seriously or promoted him.
So, while Darryl didn’t really like Michael, his reasons for that were pretty understandable. Michael also clearly saw Darryl through a lens of racial stereotypes that were unfortunate and inappropriate.
David Wallace
While Michael and David Wallace got along surprisingly well a lot of the time, there were some key moments where they were at odds.
These Moments usually involved Michael’s romantic relationships such as when he was put in the middle of the Jan Levinson lawsuit against corporate. The time that Michael was most at odds with David, however, was after David sent Holly away from Scranton after learning she had been dating Michael.
Jan Levinson
Jan is an interesting person to have on this list because these two dated for quite a long time. While they might have had a romantic relationship, they were also rivals at times.
Before they started dating, they had a relationship where Jan was always trying to get Michael to do his job and Michael was always trying to not listen to Jan. Then, even after they started dating, they always wanted different things and were more like rivals than they ever were a team. Jan at least never really saw herself as on Michael’s side.
Dwight Schrute
Michael and Dwight might have been friends, but they were also rivals. These two were sometimes friends and ing one another, and other times out to get one another. Michael often just used Dwight as a sidekick with no intention of promoting him, and Dwight, for his part, often just tried to get close to Michael because he was out for his job.
While, in the end, they did care for one another, they were also often rivals and didn’t always get along. It often felt like they were just using one another and it wasn't until later in the series that they seemed like genuine friends.
Andy Bernard
While Michael started out liking Andy because Andy would agree with everything he said, he soon learned that Andy wasn’t really on his side.
It wasn’t long before Michael got tired of Andy being a yes man and found him annoying. He regretted believing Andy over Dwight, and he had to put Andy in his place. He never really liked Andy much after that, and while they weren’t always rivals, these two definitely weren’t friends either.
Gabe Lewis
When Gabe Lewis started to work at the Scranton branch, Michael wasn’t thrilled about it. He definitely didn’t want anyone with any kind of authority in his space, and he felt threatened.
He never liked Gabe and often saw him as a rival, going so far as to get angry with Darryl for going to Gabe about an idea he had. He definitely saw Gabe as just someone from the corporate side of Sabre that was in his way, and he also thought he was weird and unlikable.
Stanley Hudson
Oscar might have thought Michael was incompetent and annoying, but it’s Stanley that hated Michael the most of all of his employees. Stanley couldn’t stand Michael and definitely hated that he had to listen to him.
He didn’t ever respect his authority which is largely understandable. While Michael tried to get Stanley to like him, it was never meant to be, and they had some moments where there was a lot of push and pull to see who would win.
Charles Miner
If there’s one rival that really got under Michael’s skin, it was Charles Miner. Charles took over Jan’s job, so he was in charge of Michael and managing him.
This didn’t make Michael happy at all after everything he’d done for the company, and he even got so frustrated that he quit and started the Michael Scott Paper Company. Miner was definitely a bit of a jerk who thought he knew everything, and Michael was also not very good at handling being told what to do when he should have been.
Toby Flenderson
The one person who Michael couldn't stand more than anyone else is obviously Toby. While Toby might have tried to be friends with Michael, it's’ clear that Michael saw Toby as a rival or even as an enemy.
His hatred of Toby could be hilarious at times, as well as a bit uncomfortable to watch at others. In Michael’s mind, Toby was the one that kept him from doing what he wanted and getting to have fun all the time at work, so he thought that Toby was the worst of the worst.