Kirk had yet to meet Trump. A late convert like many other Republicans, he had initially supported Gov. Scott Walker of Wisconsin and then Senator Ted Cruz. At lunch, Kirk sat at a table with Trump but did not get a chance to have a conversation with him. The highlight of the day instead turned out to be when Deason introduced him to two other well-heeled Dallasites, Gentry Beach Jr. and Tommy Hicks Jr., both of whom happened to be close friends with another Junior, the nominee’s eldest son. The two men asked Kirk’s thoughts on how the Trump campaign could better attract young voters. Most of Kirk’s suggestions — more campus events, a more aggressive presence on social media — were standard-issue. But he added a novel thought. “The kids need to go out there and advocate,” Kirk said of Trump’s own children. “You’d have this Avengers squad of Trumps everywhere.”
Shortly after the Fort Worth event, Hicks and Beach took Kirk to Trump Tower to meet Don Jr., who told me: “I was pretty reluctant to bring on another so-called campaign expert, especially when I learned how young he was. I said, ‘We don’t need another person who doesn’t know anything — we’ve already got plenty of those.’ But within five minutes of listening to him, I said, ‘Congratulations, you’re on my team.’” Don Jr. confessed that his campaign schedule was slapdash and that he hadn’t given much thought to how to use Twitter. By the end of their meeting, the 22-year-old Kirk decided to take a three-month hiatus from Turning Point to become Don Jr.’s scheduler, social media coordinator and steady provider of diet Red Bulls.
Following Trump’s astonishing victory over Hillary Clinton, Kirk returned to duty as the MAGA movement’s campus organizer. He drew a modest $49,000 salary from Turning Point USA, still stayed in the homes of donors and still wore a shabby wardrobe, until Don Jr., Deason, Deason’s father, Beach and Hicks chipped in to buy Kirk a $10,000 gift certificate at a men’s clothing store in Trump Tower as a Christmas gift. But things were about to change.
In 2017, he experienced the frisson of a sitting president’s retweeting his 140-character outbursts. He eagerly signed on to every available Fox News slot, cognizant of the channel’s faithful viewer in the White House. At the end of the year, Kirk attended Don Jr.’s birthday party at Mar-a-Lago. There, for the first time, he felt the stare of the president, then saw his hand motion for Kirk to come sit beside him. The two spoke for 40 minutes. At the end of their conversation, the president’s son-in-law and top adviser, Jared Kushner, walked up to their table.
After Trump made the introduction, Kushner and Kirk discussed how the administration had been getting hammered by right-wing media ever since the former Breitbart publisher Steve Bannon was pushed out of his job as White House senior adviser. Kirk assured Kushner that he was well acquainted with the journalists in question and could help broker peace. Kushner told me recently that Kirk would prove himself useful in many ways. “The thing about Charlie is that he always delivers,” he said. “When I first met him, he started out with this ambitious goal of trying to explain Trumpism to the younger generation — which, back then, popular culture and the media were against. But he was willing to take that on. And the ideas he always came to us with were good ones. He was professional, easy to deal with. Nothing ever leaked to the press. He just got stuff done.”
