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I was scribbling furiously on my oversized yellow legal pad in my Wall Street law office. Philosophy, theology and current events were splattered across the page. It was the summer of 2020, New York City was on fire, and for the first time, I was about to speak on the nationally syndicated “Charlie Kirk Show.” Yes — the Charlie Kirk, who by day was setting college campuses ablaze with blistering logic and by night was meeting with leaders of the free world.
Andrew Kolvet — Charlie’s producer and part-time model (not really, but he could be)—called for a pre-show check-in.
“Hey, man. Charlie just wants me to touch base. How big is your New York church again, a few hundred?”
“Yeah… about that,” I flatly lied. The truth was, thanks to COVID lockdowns and the exodus to southern states, Kings’ Church NYC was down to a few dozen people, clinging to survival.
I’m a pastor and a lawyer—an odd combination, I know. Andrew continued, “OK, cool. Log into Zoom and you’ll be on with Charlie shortly.”
My mind was racing: Don’t forget to say thank you. Don’t forget to mention Erika. Don’t forget to mention Descartes. The monitor flickered, and there was Charlie—sharp, skeptical, intense. I didn’t hesitate. I launched into a torrent of ideas, analysis and anecdotes. In what felt like an instant, it was over.
Then my phone rang. Charlie himself: “That was really great, man, thank you. Can you come travel with me?”
I thought he was just being polite. He wasn’t.
For the next year, I traveled the country with him. The following year, 25 more trips. Our friendship grew until he became one of my closest friends.
Charlie’s initial skepticism wasn’t cruelty — it was calculation. He was a master tactician. I met his wife, Erika, in 2019 when she was a real estate broker in Manhattan — one of the most beautiful, graceful people on the planet.
We once dreamed about starting an urban conservative news company for “the cool kids.” Then she met a boy from Phoenix who swept her away. That summer of 2020, Erika insisted Charlie put me — someone with no reputation, no resources and no platform — on his show.
Charlie wasn’t thrilled. He had plenty of voices lined up. But after Erika’s persistence, he relented, writing “FAVOR FOR ERICKA” in the notes. Hence, the reason why he looked skeptical when I appeared on the screen.
Yet, when I describe Charlie to people, I say: Imagine the greatest NFL coach of all time. He knows every play. He sees talent, places it where it needs to be and then fights relentlessly for every yard. That was Charlie. He knew every argument, deployed every resource with precision and did it all with mastery.
But behind the sharp edges was kindness. He connected with ordinary people constantly. A Florida hotel bellman once pulled me aside, glowing after meeting Charlie: “He’s so nice in person.” Another time, a vitamin shop erupted when he walked in. He especially honored older people with humility and weight — something Dennis Prager had instilled in him. He even promised my sons future work (“in the mailroom,” he laughed, “I don’t waste resources”).
On long flights, Charlie peppered me with deep questions about theology, marriage, raising children, Sabbath. He once asked me to work out with him—though I quickly regretted it. At 6-foot-2, 240 pounds, I thought I could keep up. Charlie did three sets for every one of mine. He was strong, brave and genuinely a good man.
Our Lord, the master tactician, knows every play on the field of humanity. Even in tragedy, He works all things for good for those who love Him. The seed of Charlie’s life will be multiplied into a million Charlie Kirks.
That is the strategy. That is my prayer.
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