The first idea was a run. Brennan Besser had been a 5:05 miler as a Duke sophomore — the time was posted atop the program's all-time list in the weight room, the kind of scoreboard mile that walk-ons collect when they can't collect anything else. So he woke up one morning and started running. He wanted to see how far he could go in a single push. He ran 24.5 miles. He stopped on the side of the road and called his parents. "I couldn't feel my legs. I said, 'You know what, I don't think running is going to work, but let's try to figure out what we can do to make this thing work.' Then the bike became the vehicle that would get me across the country."
The country was the United States. The vehicle ended up being a bicycle. The reason was his sister Jacqueline.
Brennan was born April 22, 1997 in Chicago, the youngest of five children and the only boy in a house with four older sisters. His parents are Charles and Rebecca Besser. Charlie Besser had founded Intersport — the Chicago-based sports marketing and content agency — in 1985, the year before he met his daughter Jacqueline's first medical specialist. Jacqueline, the second-oldest of the five Besser children, has autism. She is nonverbal. She has significantly impaired motor skills. She communicates largely through a tablet computer. By 2018 she was 23 years old, and her younger brother had been thinking about how to pay her back since he was old enough to understand what she could not give back to him in the way the world expected sisters to give.
Brennan attended Latin School of Chicago — the elite K-12 private school five blocks from Lincoln Park. He played basketball there for three years as a letterwinner. As a senior he averaged 14.6 points and 7.1 rebounds per game and shot 64% from the field, with a season-high of 19 points and a five-game stretch where he was the leading scorer. He had also played golf as a freshman and sophomore before settling into basketball full-time. He was a 6'5" combo guard with no Division I scholarship offers. He was, in basketball recruiting terms, a long shot.
But his family knew the system. His father had spent his career in sports marketing and his daughter Rachel was a New York-based creative director with deep media instincts. Brennan applied to Duke, got in academically as a political science major, and then asked Mike Krzyzewski for a walk-on roster spot. The slot opened up when Justin Robinson — Duke's previous walk-on, the son of Hall of Famer David Robinson — was awarded a full scholarship. Krzyzewski took Brennan in 2015 along with Nick Pagliuca, the son of Boston Celtics co-owner Stephen Pagliuca, as the two walk-ons of that loaded class.
He was joining a team that included Brandon Ingram, Marshall Plumlee, Grayson Allen, and the No. 1 overall recruiting class in the country.