Kirk did eventually go out and do that. But at least at first, his most important allies and friends were not other teens. They were donors, many in their 70’s and 80’s, who were also his financial supporters. He had met them on the Tea Party circuit, in hotel ballrooms and country club meeting halls, at fundraisers for local politicians and suburban gatherings where he often jumped up, nervously, at first, in an oversized suit and tie to say a few words about the country’s future and his desire to corral young Americans to the GOP.
At first, even for them, Kirk didn’t read as all that suave. In the beginning — according to Joe Walsh, then an Illinois Republican congressman who eventually had a falling out with Kirk and became a vocal Never Trumper — a lot of aging GOP donors thought Kirk seemed like a dork. Walsh says he was “a beanpole of a kid” with an awkward facial tic. Still, there was something about him they started to like. Kirk grew on you. You’d take him out for dinner and he’d devour the food like he hadn’t eaten in weeks. You’d give him advice on what to watch and he’d watch it. You’d invite him to an event and he’d come. A lot of people in Chicago conservative circles who met Kirk back then became eager to help a kid with boundless energy who supported the larger cause of saving America from Obama-ism. Eventually, they began to think that Charlie Kirk was in fact cool. And they wanted to hang with him. Kirk had finally found his clique: Old guys with money.
Kirk loved the scene. Hobnobbing with the rich agreed with him. The two biggest events, at the time, were CPAC, the Conservative Political Action Conference held every year at the end of February, and Restoration Weekend, a gathering of policy wonks, donors and up-and-comers who gathered every November to plot America’s future.
But in between these events, there was a lot of socializing for him and a band of other energetic conservative supplicants looking to raise money for their groups. All aimed to rub shoulders with donors at every possible opportunity. They knew where to go. Palm Beach was hot during the winter season. Manhattan was hot all the time. (Kirk would tell a friend that $10,000 was like lunch money for the average donor there, thanks to the high cost of living.) Wyoming was hopping with deep-pocketed hunters at the height of elk season from September to December.
Kirk likes to tell the story of his first encounter with Foster Friess, the politically incorrect born-again Christian who once told a TV reporter that women could avoid getting pregnant by holding aspirin between their knees, thus keeping their legs closed. Before arriving at the 2012 Republican National Convention in Florida where he met Friess, Kirk memorized the names and faces of the nation’s top far-right backers. He was a guy who was now doing his homework. He would bump into Friess in a stairwell and Friess would eventually cut Kirk his first big check. But there were a lot of others. Kirk’s early fans included a suburban jeweler, a pavement magnate and local Tea Party activists.
As time went on and Kirk’s star rose, his roster of supporters began to look more impressive. Eventually, he befriended a politically plugged-in Palm Beach couple, Lee and Allie Hanley. The Hanleys weren’t like some of his earlier supporters who wore athleisure-wear golf shirts and were sometimes gruff. They were an always exquisitely dressed Greenwich, Conn., couple who summered on Fishers Island, the ultra-exclusive WASP enclave off the Connecticut coast, and wintered in Palm Beach at a Mediterranean-style home designed by the iconic architect Maurice Fatio. Lee, the heir to a brick and petroleum fortune, was a Yale alum and track and field star.
Charlie Kirk became a familiar face around their Palm Beach neighborhood where, on verandas and oceanside patios during the October to May “social season,” he and other fundraisers arrived in a steady stream, and millions of dollars were promised to conservative candidates and causes.
With Allie’s influence rubbing off on him and a new stylish wardrobe, Kirk got the “makeover” he needed, Walsh recalls. He replaced his outdated suits with expensive-looking sports coats, which he paired with starched white oxfords and cool streetwear sneakers or leather lace-ups the color of desert sand. Soon, he would don hip-patterned socks and sport a voguish hairdo. His tic waned and the Chicago twang dissipated.
It wouldn’t be long before the Reagan-loving kid from suburban Chicago wasn’t just hitting up the rich for cash. He was hanging with them at their sprawling vacation homes, hunting and fishing with them, attending their lavish birthday celebrations, and having God chat with them on their boats. One fundraising executive, almost twice Kirk’s age, recalls arriving at a donor’s beach house for a meeting and noticing Kirk pacing in the backyard on his cell. He was there as a houseguest. Kirk would soon also be included in important strategy sessions with conservative powerbrokers desperate to overcome Obama-ism and take back Washington in 2016. These would happen in plush living rooms with expensive pieces of period furniture and museum-grade art, far from the McMansion-dotted suburbs where Kirk had grown up.
