Kirk finally came out and did this. But at least initially, his most important allies and friends weren’t other teenagers. They were donors, many of whom were in their 70s and 80s, who were also his financial supporters. He had met them on the Tea Party circuit, in hotel ballrooms and country club meeting rooms, at fundraisers for local politicians and the suburban rallies where he often stood, nervously, at the debut, in an oversized suit and tie to say a few words about the country’s future and its desire to bring young Americans together in the GOP.
At first, even to them, Kirk wasn’t that suave. At first — according to Joe Walsh, then a Republican congressman from Illinois who eventually fell out with Kirk and became a vocal Never Trumper — many aging GOP donors thought Kirk looked like a jerk. Walsh says he was “a kiddie bean” with an awkward facial twitch. Still, there was something about him that they began to like. Kirk grew up with you. You would take him out to dinner and he would devour the food like he hadn’t eaten in weeks. You would give him advice on what to watch and he would watch it. You invite him to an event and he comes. Many people in conservative Chicago circles who met Kirk at the time became eager to help a child with boundless energy who supported the larger cause of saving America from Obama-ism. Eventually they started to think that Charlie Kirk was actually cool. And they wanted to hang out with him. Kirk had finally found his clique: old people with money.
Kirk loved the scene. Betrothal to the rich agreed with him. The two biggest events at the time were CPAC, the conservative political action conference held annually at the end of February, and Restoration Weekend, a gathering of political buffs, donors and newcomers who gathered each November to chart America’s path. coming.
But between those events there was a lot of socializing for him and a group of other energetic conservative supplicants looking to raise money for their groups. All aimed to rub shoulders with donors at every opportunity. They knew where to go. Palm Beach was warm 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 teeming 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, keeping thus 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 country’s top far-right supporters. He was a guy who was now doing his homework. He would bump into Friess in a stairwell and Friess would end up cutting Kirk off his first big check. But there were many others. Kirk’s early fans included a suburban jeweler, a pavement tycoon, and local Tea Party activists.
As time passed and Kirk’s star rose, his list of supporters began to look more impressive. Eventually, he befriended a politically hip Palm Beach couple, Lee and Allie Hanley. The Hanleys weren’t like some of his former supporters who wore sport golf shirts and were sometimes gruff. They were a couple from Greenwich, Connecticut, always exquisitely dressed, who summered on Fishers Island, WASP’s ultra-exclusive enclave off the Connecticut coast, and wintered in Palm Beach in a Mediterranean style house designed by the iconic architect Maurice Fatio. Lee, the heir to a brick-and-oil fortune, was a Yale alumnus and track star.
Charlie Kirk has become a familiar face in their Palm Beach neighborhood where, on oceanfront porches and patios during “social season” from October to May, he and other fundraisers have arrived in ongoing, and millions of dollars have been pledged to Conservative candidates and causes.
With Allie’s influence on him and a stylish new wardrobe, Kirk got the “makeover” he needed, Walsh recalled. He replaced his outdated suits with expensive 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 be donning hip-patterned socks and sporting a trendy hairstyle. His tic subsided and the Chicago twang dissipated.
It wouldn’t be long before the Reagan-loving kid from suburban Chicago was content to hit the rich for cash. He hung out with them in their sprawling vacation homes, hunting and fishing with them, attending their lavish birthday parties, and conversing with God on their boats. A fundraising manager, almost twice as old as Kirk, recalls arriving at a donor’s beach house for a meeting and noticing Kirk pacing in the backyard. court on his cell. He was there as a guest. Kirk would soon also be included in important strategy sessions with conservative power brokers desperate to overcome Obama-ism and take back Washington in 2016. These would occur in lavish living rooms with expensive period furniture and museum-quality artwork, a far cry from the McMansion-dotted suburbs where Kirk had grown up.