A Fearsome Clash of Personalities: Passive-Aggressive Division

Winston, whom you’ve met earlier (in the post dated January 4, 2020), was a formidable founding partner at my first firm. A smallish man, well preserved, with wavy-to-curly short hair, aviator-like glasses, and a constant slight smile. Was it welcoming? Condescending? A bit of a defense?

He was a law unto himself; he allowed his secretary to draft wills. An old school type, he did everything: real estate, litigation, corporate work, wills, divorces. He even offered me a hit off of his jar of Cheez-Whiz for my home-made sandwich when we met in the lunchroom. I’m not kidding. “Give a little zip to it,” he advised.

He was a quietly uncompromising negotiator. I would walk past his office, and he was always posed the same way: phone to his ear, other arm crossed over to hold the phone-holding elbow bent, leaning back in his chair, that scary smile on his face. He always sported striped short-sleeved shirts.

From what I gleaned, his negotiating style was simply never to take no for an answer. I listened to him once, having been press-ganged into working with him. (No one wanted to deal with him as he expected his subordinates to read his mind.) He listened to the phone, letting the other guy talk himself out being his best persuasive lawyer, and then Winston would simply murmur, “We can’t do that,” or “That’s not going to work,” or something else that both refused to agree to the other side but also wouldn’t suggest a compromise; then he’d explain why, but his tone was as though the reasoning should be obvious to everyone.

Part of his confidence was based in the sense that no matter what, his client was always, completely, utterly right, so why should he back down? I found it disconcerting. What if the other side had its own no-go zones? How would the parties ever agree?

He seemed relentlessly optimistic and must have simply assumed that the other side would see the wisdom of his positions. Relentless: that was Winston. When you passed him in the hallway and said, “How ya doing, Winston?” he always responded with a firm “Better!” It got on one’s nerves. Yeah, I wanted to say, that’s what the Victorians thought about humanity, that it was improving all the time, and then World War I bit those optimists right on their fat asses.

Attempting to avoid being trapped in litigating cases, which, despite the firm’s claim to be an all-purpose shop, is what the firm mainly did, I was chiseling out for myself a specialty as a software lawyer. The widespread licensing of computer software was new in 1987, and I took to it, and, in fact, it was my real focus for the rest of my “career”.

We had firm-wide continuing legal education meetings twice or so monthly. A disregarded partner named Roger and I had become the firm’s software lawyers, and Roger let me give a presentation to the firm highlighting what were then not well-known issues in computer software licenses. At the conclusion, a jovial, kindly partner named Larry said in a voice tinged with artificial but well-meaning fear, “So what you’re saying is, if we have some transaction that includes software issues, we’d better take them to Roger or George?” There was light laughter.

Then Winston cleared his throat and spoke. I don’t recall what he said because I couldn’t follow the point of what he was saying. It seemed to have something to do with a new project he had taken on years ago.

After the meeting, I asked a young partner named Brad what the hell that had been about. He said, “That was Winston saying fuck you, there’s nothing new under the sun and he can handle anything, he doesn’t need a specialist.”

Winston marched proudly in various 4th of July parades, still fitting into his Army uniform. He was in his late 50’s. I saw him once, marching upright, arms firmly back and forth. On this occasion, what was the meaning of that infuriating slight smile on his face: see me? What a fine example I am for everyone else?

I left the firm in a couple of years, and suddenly I can’t recall Winston’s reaction when I told him. Maybe I didn’t? The partners were remarkably unkind about it. Brad, the most level-headed of fellows and more prone to laugh than to bear a grudge, invited me to a firm party a few months after I left to bid farewell to a partner who was moving to Florida. No one would talk to me.

So this next part I have only on hearsay, and even Brad, my hearsaying correspondent, wasn’t in the room. But I dearly, oh so dearly, hope this happened.

Winston’s daughter Anne went to law school and eventually joined the firm. I’m pretty sure I met her a couple of times. She was, I’m afraid, dull and unappealing. Unlike her dad, she never smiled. She didn’t have a lot of small talk or any other conversation.

A number of years after I left, she had put in the requisite years and had come up for consideration to become a partner. At that firm, which prided itself on how its being like family made it different, one would have thought that she was a shoo-in. Even I would have made partner if I’d stayed. But Anne didn’t make partner. I have no idea why.

Remember Tommy, from the post dated January 17, 2020? In sum, he was a mid-level partner, the son of a founding partner, unnaturally optimistic (“fantastic!” was his favorite answer to anything), pudgy, balding, and absolutely your best most sincere friend until he wasn’t.

Someone had to go tell Winston that Anne wasn’t making partner. I would love to have been in on all of the partnership discussions on that issue, especially the one in which Tommy was appointed to go tell Winston that his daughter had been found crucially, fatally wanting. Why not one of the founding partners? Wouldn’t that be a courtesy to one of their own? No, poor Tommy had to go deliver the bad news.

Except, as Brad told me, there was a glitch: Tommy was someone who had never given any bad news, and Winston had never heard any. So while Tommy was probably assuring Winston how much the firm appreciated Anne’s hard work and dedication and rain-making, Winston was asking which partner-sized office Anne was going to get. For all I know, they may still be sitting there, shouting “Better!” and “Fantastic!” at each other.

We all have our differing ways of seeing things, and no doubt they’re flawed. Seldom, though, do you encounter two dogged personalities so perfectly misaligned. You have to appreciate these moments.