My Best Boss (2015)

Here’s my third and final pro-journalism peek down memory lane. This post is from February 22, 2015.


The quality of one’s job is directly dependent upon the quality of one’s boss. I know this is true, for there is no other way to explain how the teenaged me managed to spend an entire summer slaving over a Burger King broiler without killing myself.

The Burger King manager, Annie, was kind and understanding. She knew the job was terrible. She knew I had grease burns running up and down my forearms. She knew I went home every afternoon smelling like a French fry. And, most importantly, she had no desire to make my life any worse. She smiled, gave me praise, and tossed me free chicken tenders the same way one might feed a trained seal. She made an intolerable job sort of tolerable and I was grateful.

My boss theory goes the other way, too. Shortly after graduating college, I worked as an assistant art director for a magazine that profiled bed and breakfasts. Even though it was a graphic design job—and I never cottoned to a career in design—I did like the work. I even found opportunities to strengthen my journalism chops, interviewing innkeepers and writing articles.

But my boss, the magazine’s publisher, let’s call her Mrs. Wilkes, was a horrible person. She fancied herself an expert in all things. One of her hobbies was to shoo me out of my desk chair and rearrange my layout. She made a big show of this, for she wanted the entire office to know what an idiot I was. Aside from the public embarrassment, what I found particularly irksome about her behavior was that when she was finally done futzing around with my work, the layout was exactly the way I had it before.

“See that?” Wilkes barked, playing to the cheap seats. “That’s the way to do it.”

Wilkes had a loose screw. She rooted through my desk at night. She threw very public tantrums. And, perhaps worst of all, she went everywhere with an ancient, toothless, hairless Chihuahua that would bite my shoes and pee under my desk.

I liked the work, but that boss broke my spirit.

Once in a while, however, you get lightning in a bottle: In the late 1990s I found a perfect job with a perfect boss.

Jack Carle was the editor of Suburban Trends, the newspaper I used to write for. The best word to describe him would be “grizzled,” for he looked a like 19th century gold prospector. He sported a thick shock of brown hair with a ragged beard to match. His rumpled wardrobe favored plaid flannel shirts and work jeans. His weathered face suggested that he had seen things that no mortal man should ever see—or could ever hope to forget.

I had never gone through Jack’s desk—I wouldn’t have dared—but if I had, I would’ve been disappointed if I hadn’t found a bottle of whiskey. He was that kind of guy. A Bottle Of Whiskey In A Desk Kind Of Guy.

Jack was large, much taller than I was—at least I think he was. He certainly carried himself as if he was large. He was also a man of few words. When he did speak, you listened carefully. He didn’t talk unless he had something important to say.

Jack didn’t yell. Never. But if he was mad, you could feel the rage radiate off of him and be frightened by it—even if that rage wasn’t directed at you.

For the record, his rage was never directed at me. Jack and I understood each other. He wanted dynamic, snappy copy. I wanted to write it. He saw that I could write it, so he left me to my own devices—which was also what I wanted. I respected Jack’s authority and Jack respected my need for independence.

But the big reason why I would’ve followed Jack Carle seven-eighths of the way to hell and back was because he defended his staff. If Jack trusted you, he’d go to the mat for you—and have fun doing it.

I covered several suburban towns for the Trends. In one of those towns there was a councilman who was a bit of a pill. For the sake of this post, I’ll call him Dave Murphy. As a journalist, it is my job to be impartial—so I will tell you in the most impartial way that Murphy was a moron. He was a showoff who loved it when the public access cameras recorded council meetings. When they did, he would yell and carry on at length, ignoring the eye rolls and impatient sighs from the rest of the council.

Those stupid cameras turned simple council matters into big kerfuffles. When the council held an up or down vote to renew a bid for a sanitation contract, Murphy used the occasion to practice his oration. “I do not think I can vote to approve this!” he bellowed. “The other morning I woke up at 5 a.m. to chat with my garbage men. I was troubled to discover that none of them spoke English!”

Murphy’s comment filled my mind with questions:

“Why would anyone get up at the crack of dawn to chat with garbage men?”

“How does mastering English improve one’s ability to pick up garbage?”

And the most important one: “Why is this man’s xenophobia wasting my time?”

Murphy’s grandstanding often turned what should’ve been a 40-minute council meeting into a two-hour one. I didn’t get paid enough for this nonsense.

So I made a decision: I would poke the bear. I would treat all of Murphy’s rants as if they were news. If Murphy wanted to talk about his garbage men’s fluency, fine. I’d write a story about it. If he wanted to say that another councilman who used to sell rotary dial telephones out of his garage in the 1970s shouldn’t vote on a cell tower contract because it would be a “conflict of interest,” fine. I’d write a story about it.

I made sure that every one of Murphy’s rants and conspiracy theories got ink.

Jack loved these stories; they fed into the mischievous side of his personality. He also loved the fact that I was cautious in my takedowns. I never editorialized, I just quoted Murphy’s thoughts and ideas. I let Murphy hurt Murphy.

Murphy didn’t like the stories as much as Jack did. He was a moron, yes, but he understood what I was doing. As soon as a Murphy story appeared in the paper, he’d call me up and yell.

“What’s wrong?” I’d ask, using my innocent voice. “Did I misquote you?”

“No,” he’d admit.

“Did I misrepresent your point of view?”

“No!” he’d admit again. “It’s your tone!”

“But if I’m quoting you correctly and representing your positions correctly, then isn’t the story reflecting your tone?”

It was at about this point that Murphy would slam down the receiver.

It wasn’t long before Murphy figured out that yelling at me was getting him nowhere. So he wrote nasty letters to the editor.

Jack would call me to his desk. “Mind if I print this letter in the next edition?” he asked.

“Sure go ahead,” I’d reply. Then Jack and I would chuckle.

When it became clear that the letters weren’t getting me fired, Murphy decided to give Jack a call.

“I demand that you fire Mr. Allegra!” he bellowed.

“Well, that’s not going to happen,” Jack said. “Anything else?”

“Well…then I think that you and I and Mr. Allegra should sit down and discuss Mr. Allegra’s conduct!”

“That’s a good idea,” Jack mused. “But, wait, I have a better idea. Why don’t you go f*** yourself?”

I laughed so hard I think I might’ve peed a little.

That kind of leadership, my friends, inspires devotion.

Jack died a few years ago, I’m sorry to say, but he is never too far from my thoughts. Once in a while I’ll raise my Chianti glass in his memory. When I do so, I imagine Jack pulling a bottle of whiskey out of his heavenly editor’s desk and joining me. He was that kind of guy. An I’m Drinking Whiskey In Heaven And Just You Try To Stop Me Kind Of Guy.

How can you not be loyal to a boss like that?

54 Replies to “My Best Boss (2015)”

    1. They did a remake of The Front Page with Walter Matthau (which really should’ve been a better movie than it was).

      But, spiritually, Jack Carle had a lot more in common with Ron Swanson, the Nick Offerman character in Parks and Recreation.

      1. Actually, His Girl Friday was an adaptation of 1931 film The Front Page (which was adapted from a stage play of the same name). Then, much, much later on, Billy Wilder adapted it again with Matthau and Jack Lemon.

        Dang. Why do I know all of this?

      2. I have never watched Parks and Rec. Am I missing out? My students have spirited discussions which is better: Parks and Rec or the Office (not a fan of working place mayhem and inept bosses).

      3. If you don’t like working place mayhem and inept bosses stay away from The Office. Parks and Rec is a very funny show with a lot of heart. I would highly recommend giving seasons two and three a whirl.

      4. I suppose I should give it a whirl in order to remain conversant with my students. They are beyond disbelief that I have never read Harry Potter (don’t intend to either). They are amazed I don’t drink coffee either. Yes, I am that weird English teacher.

      5. I arrived to the Harry Potter party too late, I guess. Everyone was touting the series as the best thing since sliced bread and I expected more than what I ultimately got—a competent and entertaining story that wasn’t nearly competent or entertaining enough to persuade me to pick up book 2.

        But I don’t think I could ever forgive you for not drinking coffee.

  1. I laughed so hard I think I might’ve peed a little. <—I did that to Jim's post this morning. And to you with this line this morning. *toddles off to the loo*

    I haven't had any bosses like you speak of Jack. As I'm coming to an age where I REALLY want to retire…I find that sad.

  2. I really like Jack! He was the perfect boss for you and encouraged your creative expression. Did not like control freaks (I know best) Mrs. Wilkes! Ugh!
    I worked with a lot of bosses, some had big egos and got a way with murder by management especially when I worked for the Senate and the USAF. But, I always seemed to find a way to get along with most — except for one 3-star General. He would yell in staff meetings, get red-faced and stop briefings and walk out leaving people trembling and scrambling to meet his demands — which was an impossible defeat. He even turned his back in a very rude manner on a group of community leaders visiting his office. They were speechless. I knew we would not do well on certain projects, so I let a member of my staff he liked always travel with him. It caused his chief of staff to be on edge. Fortunately, they only stayed two years before they moved on to another command. But, for the most part, I had a lot of respect for the people I worked with.

  3. I think we all should raise a glass of whiskey to Jack. Not only was he a great boss and a great journalist, he encouraged you to be become the great (and humorous) writer that you are. CHEERS!

  4. A boss like this “best boss” will pick you up and make you forget all of the terrible ones! In my teaching career, I had principals (read ‘bosses’) of both ilks. It’s years since I was in the business of education, and I have completely forgotten the negative guys, but will always remember and adore the best ones!

  5. I like Jack, too. He reminds me of my dad. I did journalism for a while and was pleased to have a good editor. Having to cover those council meetings was the worst, though. They were soooooooooo boring. At least for you they got lively.

    1. Once I got used to the rhythms of council meetings, I found them interesting. They were also a journalism challenge of sorts: How many news stories can I get out of this meeting? My personal record was six.

      1. I suddenly realize that I’ve turned this into a competition. sorry! Didn’t mean to. Even if my experience was definitely, totally worse than yours! 😉

  6. Jack sounds great, but what I really liked about this post was your ingenius way of besting Mr. Murphy by showcasing his stupidity with his own words.
    Sometimes we say things that if we read them later in print, we’d agree they sound stupid.

  7. What a great post, Mike. I think I remember reading about Jack before and I’m sorry that he’s no longer around to be someone’s boss. We need more bosses that have their employees’ backs. And I love the way you describe people. You get to the core of their personalities and it’s a joy to read your writing. 😀

  8. We should all be so lucky as to have a boss like Jack! Sadly, I am more familiar with the Mrs. Wilkes type. Though that experience helped me to deal with another boss ( I’ll call him Mr. J) who occasionally was known to have Wilkes like tendencies. When I applied for that particular job and stated my reason for leaving is that my boss was a daily screamer and I put up with it for two years before deciding I’d had enough. During the time I worked for Mr. J I had seen him rip into a few people….but he never raised his voice to me. I think he was afraid I’d quit and I never said anything to convince him otherwise. Life is too short to work for a**holes.

      1. Sad…but true! On the other hand, bloggers are awesome, helpful and generous. Perhaps this will make up for the bosses, eh?

  9. Obviously Murphy was a buffoon and you handled him perfectly. I feel like I knew Jack. My version of Jack was Lorne and he was my boss at a TV station. He still sends me off colour jokes on my birthday. Never forgets.

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