Five years ago, I recorded this interview with Bill Montgomery outside Trump Tower Chicago. Bill passed away on July 28, 2020, at age 80. Today, with Charlie Kirk’s tragic assassination at Utah Valley University, this footage takes on profound historical significance. This is the real story of how Turning Point USA began – not in a boardroom or with venture capital, but when a successful businessman saw an 18-year-old speaker wake up 400 sleeping high school students in just 20 seconds.
Bill Montgomery was attending a demonstration at Benedictine University in Illinois. The event was designed to show 400 high school students the difference between Tea Party and Occupy Wall Street movements through mock demonstrations. Six speakers had already gone up – three from each side. The kids were bored silly, falling asleep in their seats. Bill was checking his watch, hoping the seventh speaker wouldn’t drone on too long.
Then something extraordinary happened. As young Charlie Kirk walked to the podium, Bill witnessed what he would later call a miracle. In exactly 20 seconds, Bill watched 400 teenagers transform from practically unconscious to wide awake, leaning forward, completely engaged. The shift was so dramatic, so instantaneous, that Bill knew he was witnessing something special.
After the speech, Bill Montgomery made a decision that would alter the course of American political history. He approached this unknown 18-year-old and said words that Charlie would never forget: “Charlie Kirk, you don’t know me, but you can’t go to college.” Charlie was already accepted to Baylor University, his future mapped out like any other bright young student. But Bill saw something greater – a gift that couldn’t be confined to a classroom.
What followed was two and a half years that Bill would later call “the most fun and exciting time of my life.” He and Charlie traveled all over the country, building what would become Turning Point USA from scratch. The logistics were almost comical – Charlie was too young to rent a car or check into hotels, so Bill handled everything. They were an unlikely pair: the successful older businessman and the teenage firebrand, crisscrossing America with a message of freedom and conservative values for young people.
Bill’s wife would later joke that after those two and a half years, she “got her husband back.” The sacrifice was real. Bill gave up his comfortable retirement years, time with family, and personal comfort because he believed in something bigger. He believed, as he told me that day in Chicago, that “this country was going to be saved” through reaching young people.
They started in a two-car garage in Lemont, Illinois. Not even a house – just a garage. No investors breathing down their necks, no corporate infrastructure, no safety net. Just two men with complementary skills and an unshakeable belief that American youth were hungry for truth. From that humble garage in a Chicago suburb, they built an organization that would eventually reach millions of students across 3,500 campuses in all 50 states.
In this October 2019 interview, recorded just after President Trump’s visit to Chicago, Bill’s optimism was infectious. “We are going to turn Illinois red,” he declared with absolute certainty. His eyes sparkled with the confidence of someone who had already seen the impossible happen – who had watched a teenage speaker transform 400 minds in 20 seconds and knew that same transformation could happen nationwide.
Neither of us knew that day outside Trump Tower that Bill had less than a year to live. Neither of us could have imagined that Charlie, the young man Bill discovered and mentored, would be assassinated at age 31 while doing what he did best – speaking truth to college students. The mentor and the protégé, both gone now, their work unfinished but their impact undeniable.
This interview captures more than just an origin story. It captures the essence of what made the Bill and Charlie partnership so powerful. Bill brought wisdom, resources, and connections. Charlie brought youth, energy, and an almost supernatural ability to connect with his generation. Together, they proved that movements don’t need massive funding or establishment support – they need vision, sacrifice, and the courage to tell an 18-year-old to skip college and change the world instead.
Now they’re both gone. Bill Montgomery, who gave up his golden years for a cause he believed in. Charlie Kirk, who gave up a normal college experience to become a voice for millions. But movements built on truth dont die with founders. Every student who questions the narrative, every young person who finds their conservative voice—that’s Bill and Charlie’s legacy.
Watch Bill share this story. See the joy in his eyes as he remembers those early days. Hear the certainty in his voice when he says America will be saved. This isn’t just history—it’s proof ordinary people can create extraordinary when they have the courage to act.
