The first time I met the worst example of a boss I can imagine, he was kind to me. Daniel was new at the company; I was finishing my first year there. I loved my old boss, but I was still eager to meet Daniel because I understood that change was inevitable. I entered the office that day and there he was, waiting, his eyes already revealing a desperate need for approval that should've set off an immediate alarm. I was 23 years old. He was pushing 40.

At the time, in 2009, I was unaware of the needy, conflicted person behind those eyes. In less than a year, I would learn exactly how hopelessly damaged Daniel was, and I'm still left wondering what he was worse at: being a manager or a human being. Though that gray area lingers, one thing is for certain—we became embroiled in a one-sided rivalry that I wanted no part of. What I later learned was that it is impossible to work for someone who's competing with you.

The relationship between me and Daniel wasn't always contentious. He was hired to introduce change to the marketing department in the company's Washington, D.C. office: to create synergy, streamline processes for efficiency, and all of those other hollow, corporate buzzwords that huge, fractured media organizations toss around when they want employees and clients to drink the Kool-Aid.

I had been touted as a budding prospect by upper management, and was open to his ideas. Initially, we got along fine. And unlike many of my office colleagues, Daniel and I formed a pretty strong bond. He would rave about President Obama, who had just been elected, and proudly railed against the white privilege he admittedly benefitted from. I found some comfort in knowing I had a boss who seemed to grasp the dynamics of race relations in the workplace. But others were resistant to the procedural shift he was brought on to implement. That, and they found him unpleasant. This made Daniel an outcast from the beginning, while I was generally well-liked. At the time, I was too young to realize that this contrast would become the catalyst for all of our problems.

People fail miserably at innovation when they tinker with things that aren't broken. Daniel fell victim to this, and it wasn't because of his zeal to prove what an adept problem-solver he was. After eight months of having his methods questioned, he decided to upset a working system and move me into a different role—one which was far more stressful. He said I was "perfectly capable of handling the challenge," but my best interests aren't what brought him to this conclusion. A co-worker later told me, he did it to piss me off.

Involuntary bonding is commonplace in the corporate world. Forced fun is passed off as "team building"—which involves stale conversation over mediocre meals paid for by expense accounts and loaded intentions. Instead of trying to unite our department through common interests and happy hours at shitty bars, Daniel did it by sharing his unhappiness with us. He was unhappy with the long-distance relationship he was in, he was unhappy with the debt he had accrued, and he was unhappy with where he was at in his career. Daniel's unhappiness quickly became our collective problem.

My co-worker Sarah was Daniel's first target. Despite being nearly 15 years his senior, he treated her like a child who suffered from learning disabilities. Their struggle to communicate was difficult to witness, and the disrespect grew more intense as time went on. He talked down to Sarah regularly in the way that an exasperated owner talks to their pet, and the mental and physical toll it took on her was obvious. It eventually got so bad that she quit before finding a new job. It was affecting her health. Imagine the experience of going to work being so dreadful that it literally makes you sick. Considering Daniel once told me that he had a frightening meltdown from a job he despised, you'd think he'd have some compassion. But no.

There were more telling incidents. Daniel disliked Bobby almost instantly. He saw him as a bad influence on me, and a link to our previous manager's regime, something he was exceptionally insecure about. Daniel was the new coach who didn't want to hear anything about the old coach, as if the mere mention of her name was an insult to his very existence. After Bobby accidentally called him a "prick" in a message intended for me, Daniel began to seek out faults in Bobby, over-analyzing his every move, harassing him about being away from his desk, even if it was just to go to the bathroom. The smallest issues were amplified in an attempt to build a case against him. This obsession was disturbing, and it reached a new low when Bobby's father's health began to deteriorate.

Daniel was everything that James Hetfield sang so passionately about on Metallica's "The Unforgiven" and everything that drove Walter White to infamy on Breaking Bad: a middle-aged man who never got to have his moment in life.

Bobby began requesting to leave work early to go see his ailing father, either using his flex time or promising to come in early and stay late other days to make up for it. Daniel was convinced Bobby was lying right up until his father passed away on Christmas. One of our co-workers told me she watched Daniel break down and cry about it in his office. He confessed to feeling like a terrible person. Once again, you'd think this would compel him to do some serious self-evaluation, but that never happened.

Months later, when Bobby was searching for a new job, word got back to him that prospective employers had been reaching out to Daniel as a reference. Considering the history between he and Bobby, you'd expect he'd want to see him go. Not Daniel. He advised people not to hire Bobby because he didn't want him to move on—although he had tried (and failed) to get him fired. Jay Z had it right: "Niggas want you to be miserable with 'em."

Daniel disrespected Sarah and flat-out loathed Bobby, but what went on between he and I was uniquely toxic. He would say things like, "You're gonna take my job," or "You're gonna be my boss one day" with a look of fear in his eyes that made me uneasy. I was younger, taller, finished college, and grew up better off than he did. I represented everything that he wasn't, a mirror for all his shortcomings. I never held any of this over him and never once felt like I was better than him, but the jealousy was evident. Other co-workers acknowledged Daniel's awkward jealousy, too. Mostly, I just tried to ignore it.

Lack of outlets aside, Daniel's biggest problem was his dissatisfaction with himself. He realized that the company had hired him to fill a hole, not to see him flourish. While I showed up to work everyday with a grin on my face because I enjoyed the world outside of it, he felt stagnant and had little to do past 6 p.m. Boredom, confusion, and malicious intent are a hazardous combination, and this virulent blend only fed his crab mentality.

By this point, the dynamic between Daniel and I had been irreparably damaged. I no longer respected him, but we still had to work together. But the problem was that he hated doing actual work. If he had his way, he would just delegate tasks and take the credit for our efforts. His spite started a pathetic battle where he'd attempt to outshine me, while I wanted nothing more than to finish my work, go home, and enjoy life. When he wasn't increasing my work load, he was wedging his way into situations I managed by asking to help or take the lead—only to back off when he realized it involved exerting real effort, which would occupy the time he spent watching reality TV in his office.

As our relationship continued to sour, I became his frenemy. I make the distinction that I was his adversary because this situation remained one-sided. Whatever irritated me about work I left at work; Daniel took it home and lived with it. It was all he had. Worse, rather than fix what was wrong with his own life, he chose to concern himself with mine, and I sensed he still wanted to be friends. But your coworkers aren't your friends. You might become friends with some of them over time—and it's great if you do—but that shouldn't be an expectation. I made the wise decision not to befriend my manager who, once freely admitted to me that he was "spiteful and vindictive." This was after he'd harassed other members of our team. Would you date someone who told you they cheated on every significant other they had? Probably not.

His attempts to bond were a warning sign. It was also a huge indicator that you can never work directly beneath someone who's threatened by you.

Several complaints were filed against Daniel, but the worst he suffered was a slap on the wrist and a stern talking to. His boss— the boss—once told him to take some time off after he flipped out on too many of the wrong people. But paid time away from work is hardly punishment for someone who was allergic to doing work in the first place. Daniel cowered behind the same shield of white privilege and, more specifically, white male patriarchy that he denounced so vehemently when I first met him. He was further enabled by the fact that his boss neglected to take any serious action against him since it would make him look incompetent for hiring such a petty individual. No one at any level in corporate America wants to admit fault until it's absolutely necessary, even if an entire department suffers as a result. Daniel was proof of that.

I've since moved on from that office—so has Daniel—but the the lessons remain with me. Let's be honest: if a bitter person with insufficient self-confidence can impact your success, you need to remove yourself from that situation. Few things are more pathetic than someone in their 40s seeking validation from a 25-year-old, but his behavior made sense. For him, work was like high school, a difficult time that provoked several unresolved issues. Daniel was everything that James Hetfield sang so passionately about on Metallica's "The Unforgiven" and everything that drove Walter White to infamy on Breaking Bad: a middle-aged man who never got to have his moment in life. Those are the most dangerous people.

Julian Kimble is on Twitter. You can find him here.

[Illustration by Jim Cooke]