The Most Interesting Man in Chicago
There was a time in my early 20s when I frequently found myself enamored of a certain kind of man. The kind of man I’m talking about was not old, but he was older than I was. He was not smart necessarily, but he see med to have found a way to harness what intelligence he had toward worldly ends. He was generally high achieving, charismatic, and accomplished in a chosen field that earned him a comfortable living and substantial degree of respect.
This time in my life — of being easily enchanted by powerful men — ended long ago, and yet every now and then I end up revisiting it, wondering what it is that gives these men their power. One such occasion was a cool morning in June, when I found myself riding in the passenger seat of a quarter-million-dollar sports car alongside a man named Joseph Siprut. It was Father’s Day, and as we careened onto Lake Shore Drive, I couldn’t help but remember the joy of riding beside my own father, also a sports car enthusiast — the carefree, joyful, slightly infantilizing exhilaration of keeping a man company as he ushers you in high style down an open highway.
To call Siprut’s Aston Martin Rapide S a sports car now strikes me as an under-statement. From the passenger seat, it felt more like a rocket or a bobsled. I’ve grown accustomed to the height of a minivan, and the always impressive Chicago skyline appeared even more imposing from this low-slung vantage point. Indeed, I felt so close to the road, I marveled at the fact that the vehicle wasn’t scraping the asphalt and catching on fire.
An Aston Martin, in case you need reminding, is the sports car driven by James Bond. Joseph Siprut is not an intelligence officer in MI6, but he is a lot of other things: the managing partner of one of the country’s top-ranked class-action law firms, a successful film actor, a competitive wrestler, and a multimillion-dollar hedge fund manager, to name a few. By the time he took me for a drive, I’d come to think of him, this chiseled, boyish, almost pathologically polite 41-year-old playboy, as Chicago’s Jay Gatsby. Like Fitzgerald’s character, he seemed to inhabit a gilded world most of us can only gaze at from the outside. He emanated an aura not just of wealth and success and charisma, but of overflowing goodwill. As I rode beside him, I imagined that in a world he created, there’d be an Aston Martin for everyone.
“So,” I asked him that morning, “why this car? Does it handle better than other sports cars?”
“Nah,” he said. “I just like what
