The Worst and Best Bosses In TV History

David B Morris
7 min readFeb 11, 2022

Part 2: Television Bosses You’d Be Glad To Work For

Good police doesn’t give him enough credit.

Now let’s deal with some bosses anyone of their employees would be proud to work for.

Wonderful Bosses

Cedric Daniels, The Wire

Sure he was political as anybody in the Baltimore Police Department and he knew how rigged the game was. But anyone who worked for Daniels over the five seasons of The Wire — with the exception of gadfly Jimmy McNulty, who had problem pissing on the authority of the man who’d brought him back from the dead — knew that he always had your back. He was always there to stand between you and the Commissioner, even if it ended up costing him. He believed in the Barksdale case when no one else did. He saw the possibility of a major case squad in a department that had no use for it. And he always was willing to challenge authority, even the Bureau when it came for it. No doubt he would have made a great commissioner — but that same integrity that made him a great leader of men was ultimately the same thing that the broken political system of Baltimore could not tolerate. Lance Reddick has a grand tradition of playing authority figures and it started with being the ultimate compliment on The Wire — a boss who could also be ‘good police’.

Adam Schiff, Law and Order

For the first decade of Law and Order’s incredible run, the one thing fans of the series could count on was the dignity — and acerbic wit — of Adam Schiff. He would be just as friendly to the conscientious Ben Stone’s often merciful prosecutions as to Jack McCoy’s contortions of the law (though too be clear that did cause him quite a bit of agita in the last two years of his time). Steven Hill was one of the great actors of our era, and he often the less he said, the more significant his dialogue could be. To be sure the few times we got a look at his personal life, it was inevitably because a close personal friend had committed a major crime which he would end up having to prosecute but unlike every other DA that would follow — including Sam Waterston’s Jack McCoy himself — he cared less for the politics of the job then for the rightness of the law. He was even willing to go against the governor himself if he thought he was in the wrong. Law and Order was never the same series after Schiff left the DA’s office (we never did learn why Hill left the show) and it’s mainly because no one else in the office knew how to demonstrate loyalty just by saying a few words.

Yes, he was a cutthroat but he was worth working for.

Al Swearengen, Deadwood

Anyone who has a loose knowledge of Deadwood must be doing a double take right now. Al Swearengen, the foul mouth pimp/thug/murderer who was the head of the Gem? A cutthroat leader who literally cut throats? Hear me out. No one (especially not Ian McShane, who memorably portrayed him and definitely not David Milch, who brought him to life) would dare to call the man a saint. But sometimes the era and the place call for a different kind of leader, and 1876 Deadwood definitely did. Sure he had no problem swindling rubes, beating up prostitutes and flunkies, killing the odd felon and feeding him to Wu’s pigs. But consider the loyalty that he managed to command in the camp. Not just all of the people who worked at the Gem, but Bullock and Silas Adams and Merrick. Even Farnum, who he was always belittling and insulting, was loyal to them despite it, maybe even because of it. Hell, when the time came to form a government, of course Swearengen led the meeting. Of course the camp panicked when it seemed certain that Swearengen would die of kidney stones. And when the time came for the inevitable battle of capitalism against George Hearst and the like, Swearengen did his best to lead the fight. Swearengen was a monster, no question. But the Wild West often called for men like him. Milch once said that there might have been a universe where Swearengen could have been President. Considering some of the politicians of the era (and now) we could have done a lot worse.

How do you file a UFO abduction as a travel expense?

Walter Skinner, The X-Files

Yes, he spent almost his entire time running the X-Files in the grey area and was almost always berating Mulder and Scully. But as long as he was there, he always had his agents’ backs. (And let’s face it; he probably deserves a prize for being able to read the reports of a mammoth alien conspiracy and monsters-of-the-week not only with a straight face, but somehow getting those files through a government bureaucracy for nearly a decade.) He talked Mulder out of resigning with a monologue about his experiences in Vietnam that was one of TV’s greatest moments. He was willing to make a deal with the devil to try and save Scully from cancer. And the scenes where he stood up against the insidious Cigarette Smoking Man are some of the show’s highlights. (‘This is where you pucker up and kiss my ass’ is one of the great retorts I’ve ever heard on television.) And when the series went into its dying fall after David Duchovny stopped being a regular, Mitch Pileggi’s work after witnessing Mulder’s abduction was one of the series great treasures as he would help an often beleaguered Doggett and Reyes through a world they were rarely prepared to travel. I know what happened to him in the ‘final’ season finale, but I refuse to accept it. After all, no one ever really dies on The X-Files.

Sharon Rayder, Major Crimes

I may be in the minority in that I much preferred the spinoff of The Closer far more than I liked the original series. And a large part of the reason was the decision to put Mary McConnell’s Captain Rayder front and center. I always liked her when she represented the Force Prevention Unit on The Closer even though (and maybe even because) she was often clashing when Kyra Sedgwick’s characters way of doing business. (And as anyone who watched some of the actions Brenda Leigh Johnson took throughout the entire series, it’s kind of amazing she kept her job for seven seasons.) Rayder had the same loyalty to her men that Chief Johnson did but she had more integrity and compassion than we ever saw Sedgwick show in her time on The Closer. I may not have liked the storyline that involved Rusty that made up so much of the series backbone, but you could never a million years she Brenda as being the least bit maternal. And it gutted me in a way so many other character deaths on television never have when Rayder died of heart failure near the end of the sixth and final season just as much as it did the entire unit. Television needs more cop series like Major Crimes and more bosses like Sharon Rayder.

Jacqueline Carlyle, The Bold Type

So many times in entertainment journals and online reviews of The Bold Type I would hear Jacqueline, the editor-in-chief of ‘Scarlet’, described as ‘the best boss ever’. And honestly the hyperbole was very close to be accurate. It wasn’t just the way she mentored Jane, Kat and Sutton in different ways throughout the series run, it was that she was compassionate to everybody on the series even when they made mistakes. It was that she was willing to fight the people upstairs for the story and for critical issues, even when it cost her job. And if the story was important enough that some other part of the company had to publish it before Scarlet, well, she would put her ego ahead of the byline and let it happen. She was friendly even with the people who clearly wanted her job or her out of the way, and she was a loving wife who at the end of the series left the magazine so that she could have adventures with ever patient husband. Melora Hardin did a stint on The Office (and considering how much damage Mike ended up doing to her character on that series, she deserved a bonus) so its possible she could have lifted Michael Scott’s Best Boss Ever mug from his desk. I can imagine everyone at Scarlet wanting to give her a real one.

Wow. I had so much writing this one that there’s a very good possibility there will be follow-ups in the future. God knows there are more than their share of bad bosses on TV and quite a few good ones.



David B Morris

After years of laboring for love in my blog on TV, I have decided to expand my horizons by blogging about my great love to a new and hopefully wider field.