So I worked for this guy named Lee. And Lee was alright.
I should start by saying that I work for attorneys currently and most of them are, lets say, dickish. Now, I don’t want to cast a wide net and generalize an entire field. There really are a lot of great attorneys that are good and decent people and work to make the world a better place in whatever small way they can. Those people are commendable. My best friend, Justin, he is one of those attorneys who I believe are actively trying to help people. But I have also worked with attorneys for a couple of years now and it’s been my personal experience that although many have good intentions, they broadly come off as cunts. At least to me.
Perhaps my experience is not representative. I am perfectly willing to accept that maybe I have just been unlucky after working four years in the legal field. Much like you have the same chances of winning the lottery by playing 123456, no matter how unlikely that sounds, I may have just happened to come into contact with an improbable niche of attorneys that happen to be self-important assholes. Statistics are weird and anything is possible.
But perhaps this is why Lee stood out a bit in a sea of otherwise deplorable people. The guy, for all his flaws, was pretty down to earth. That’s not to say that he wasn’t rich or disconnected from the struggle of the average person. He certainly was. But he was also approachable. He didn’t talk down to you unless you were a woman. And I know what that sounds like, but this guy was pushing seventy when we first met, he had been a lawyer for over half his life, the fact that he didn’t call his assistant ‘honey’ in casual conversation was impressive enough. Sometimes we need to grade on a curve.
That’s actually not even true, I just thought it would be funny to say and now I feel bad about it. For the most part, he was a pretty stand up and respectful guy. He enjoyed hanging out with the staff, a small gesture which should not be of note considering that we are all humans, but you have to understand how some of these rich guys work. They treat conversation with the staff as if it were an act of charity. They enjoy being praised for how well they get along with the Joe-Schmoes of the office. They treat their pathetic fist bumps and condescending pats on the back as if it were a treat. “Look how down to Earth I am.” It’s a little gross.
But Lee, Lee was alright.
He was born to a Jewish family, big surprise there. He grew up pretty comfortable financially thanks to his dads’ hard work. Went to school and got a law degree. Moved down to Florida from New York and started working in Community Association Law. And yes, that is as boring as it sounds. He made a living of it, met a girl, fell in love, got married, had two kids, helped his wife start a million dollar business, and he kept right on working. When I met him, he did not really need to work, and if I’m honest, he barely did. He would say he just kept working because he would go crazy at home.
He liked to come into the office and walk around. He’d shoot the shit with everyone about movies, books he read, TV shows he was watching, politics, whatever happened to be on his mind really. We spoke frequently and to the detriment of my work. I even got in trouble once with one of the higher-ups because I spent too much time talking with him. Often, he would ask me for help with his iPhone, the guy was aggressively bad with technology and very vocal about his disdain for it. I was slightly annoyed sometimes because I do try to get work done in between scrolling through Reddit articles, but I never truly minded. That’s just what he liked to do. He came in just to interact with people. He didn’t care if they were lawyers or IT guys or assistants. He would be happy to stand by your desk and talk shit about anything he found interesting at the moment. For the most part he was likable, sometimes he was a little creepy with women in the way rich old white men can be. But for the most part, he was a cool guy.
Some months back, he was playing tennis with his daughter. Lee really enjoyed playing sports, he did so all his life, in fact, he was still occasionally playing football when I met him and he was in his mid-sixties. He particularly enjoyed tennis, it was easier on his body so he played often. In this particular day, his daughter was visiting and they were enjoying the rare pleasure of playing together in a couples match. At some point during the match, Lee’s daughter reared back and he accidentally ran his leg into her racket. It ended up doing some serious damage to his Achilles tendon and landed him in a cast for a few months. This happened to his right leg which meant he couldn’t drive.
Lee knew I drove passed where he lived on my way to work and asked if I could give him a ride every now and then. I obliged. I didn’t do it because he was technically my boss. At least, I don’t think so, not entirely anyway. I’d like to think I would do that for anyone under similar circumstances. To be perfectly honest, I did feel a little uncomfortable about it but I liked the guy, so I was happy to do it.
I live a little far from work and if there’s traffic it’s not uncommon to spend over an hour on the road. The first day I gave Lee a ride I feared that it might be awkward, but to my surprise, we spent that entire hour talking incessantly until we got to work. We talked about anything and everything. But it was largely politics and our philosophies in life. He would try to impart lessons and I would laugh at his casual racism while I tried to push back and explain why some of his views were problematic. We agreed as often as we disagreed. He would excuse his stubbornness as wisdom and assured me that he was ideological like me once, but age and experience cured him of that ill with the medicine of pragmatism. We carpooled for a few months and every single ride was filled with long and pleasant palaver. I even started looking forward to those drives.
I got to know Lee fairly well. He and I were friends, of a kind. I knew some pretty personal things about him. Things that people who worked with him for decades didn’t know. We had moments of deep introspection in those rides, moments of honesty and vulnerability. I would tell him about my fears of not finding a fulfilling career, about growing up in a broken home, about my anxiety and struggle with self-sabotage. He would tell me about his fears of growing old, about the indignities of not being able to care for oneself, about wishing that his kids reached out more, that they spoke to him more.
I mentioned my friend Justin earlier. We went to school together in Tampa; I had a car and he did not. I would give him rides back home to Miami whenever I went south. Those were long, four hour car rides in which we did not shut up for a minute. We talked about sports and love and life. We got to know each other really well in those rides, those rides helped forge our friendship. Driving Lee to work felt a little bit like that.
Lee stopped showing up to work for a couple of weeks. I heard he got sick, something about the flu. I texted him and asked if he needed a ride, he told me that he didn’t, he was not going to be working for a while…
Lee died about a month after our last ride together. He had a brain tumor and the doctors caught it a little late. He had several small strokes that landed him in the hospital; a week after, he was dead. Just like that.
Our last text exchange went like this:
“Hey Lee, if you still need a ride I’ll be there around 8:45. Let me know.”
“Not today thanks. Still sick.”
“Sorry to hear that Lee, hope you get better soon.”
This was on February 14 at 8:35 a.m.
Those were my last words to him. “Hope you get better soon.”
All those conversations we had; the funny, the controversial, the intimate, the silly… My last words to this guy were pleasantries he saw through a small screen he probably had to squint to read. I guess I did not want to overstep. I guess I was a little uncomfortable with the relationship since I technically worked for him.
It’s a strange thought now. We were not really close as one would say. But we were friends, in some form of the word.
It is not uncommon to think back about our last words to someone and regret them. Being aware that the person you are talking to will die soon would be an interesting cheat code for human interaction. I’d like to think I would have made a stronger attempt at connecting with Lee in a more meaningful way if I knew things were as serious as they ended up being. I wish I would have known and talked to him about how it made him feel. I wish our last conversation was one filled with compassion and comfort.
But that’s not how things work unfortunately. Sometimes you don’t get do-overs and your last words to a human being are “Hope you get better soon.” Then we have to live with that forever. Knowing that you could have been more impactful with your time and chose not to be, due to whatever small, petty thing that is the source of your insecurity. It’s never worth it. We have all heard the story before.
It could have been worse. It could have been a best friend, or a sister, or a mother. My last words to someone I genuinely love could have been pleasantries, as they were to Lee. I have been thinking about that a lot since I found out he died. If my last words to my mother were a lazy and empty attempt at finding out how her day went.
“Hola mama, como esta todo?”
Then Boom! Car crash. Heart attack. Aneurysm. Ninjas.
And my last attempt at a genuine human connection was as vacuous and reflexive as saying ‘bless you’ when someone sneezes.
There’s not a new lesson here. This is all essentially a repackaging of those trite sentimentalities you have all heard before. Nothing new to gain here aside from another anecdote of a squandered opportunity leading to regret. And what’s funny is that ultimately, this is all me feeling bad for myself because I was not content with the way I felt about my lack of humanity. Fifty percent of this is the dead guy. But the other half is about me. And that makes me feel uncomfortable.
But maybe in the end it’s a normal empathetic response to absorb loss through the filter of self. Maybe the death of this old rich dude helped me realize a little something about myself in the end. Maybe losing a friend, or whatever he was, crystallized certain realities that I understood intellectually but never truly pondered. Maybe that’s why shortly after finding out about Lee’s death I texted everyone I cared for and let them know I loved them. Because realizing that one can be here and then suddenly not, serves as a strong incentive to make sure that the last memory someone has of you is one that leaves them with a smile on their face, rather than with a feeling of indifference. Because life is much too fleeting to let petty insecurities prevent you from connecting and bonding with people in a meaningful way. And maybe after all the lessons that stubborn old man tried to impress upon me, this last one was the most important and the one that I hope will stick.
So, thanks Lee.