Woodside is the rich-on-the-rocks Silicon Valley town in the foothills behind Stanford, where the streets are unpaved by design and the houses sit far back from the road on horse pasture. There aren't a lot of NBA-track basketball recruits coming out of Woodside. There are a lot of Stanford prerequisites, lots of country-club tennis players, lots of squash courts. Simpson wasn't built to be a Woodside kid. He was built to be a Duke basketball player — or at least a Duke basketball player's idea of what a Duke basketball player should look like: 6-foot-4, lanky, smart, a long-range shooter with the kind of work-ethic-over-talent profile that recruiting services rank at zero stars and assistant coaches notice three minutes into the first scrimmage.
Simpson attended St. Francis High School in Mountain View, the Catholic prep about 15 minutes north of Woodside whose basketball program had produced two NBA draftees in the 1990s. He played there through his senior year of high school, then did what an under-recruited West Coast prep guard with Division I ambitions sometimes does — he packed for a postgraduate year at New Hampton School, a small boarding prep in the New Hampshire woods that, by the late 1990s, was on its way to becoming one of the country's premier basketball prep finishing schools. The New Hampton program would eventually produce Noah Vonleh, Sam Cassell Jr., countless ACC and Big Ten recruits, and would help establish the modern PG-year basketball path. Simpson was one of the early arrivals on that path. The year was 1997. He used it to refine his shot, fill out his frame, and chase the school he wanted.
That school was Duke. Mike Krzyzewski had no scholarship to offer — the 1997 recruiting class was already loaded with the eventual NBA careers of Elton Brand, William Avery, and Shane Battier — but the coaching staff did have the one thing Simpson cared about: a roster spot for the right walk-on. He'd practice every day against the best players in the country. He'd travel with the team. He'd be on the same bench as Coach K. The basketball would be the best he'd ever play. The seasons would matter. The roster spot, on a team like that, was the scholarship. Simpson took it.