High School Career
Stephenson first caught the attention of scouts at age 12, when Clark Francis, a talent evaluator, saw him play at Rumble in the Bronx AAU tournament. And before his first year of high school, he attended the Adidas ABCD Camp, where he challenged O.J. Mayo to a one-on-one game.
In the summer of 2005, Stephenson enrolled at Bishop Loughlin Memorial High School, but he only attended the school for three days, before the school lost in the championship game of a youth league and he did not win the tournament MVP. The following week, Stephenson did not return to classes at Bishop Loughlin, and was attending Abraham Lincoln High School near his home in Coney Island. National Basketball Association players Stephon Marbury and Sebastian Telfair had also attended and played basketball at Lincoln High. Head coach Dwanye Morton said, "{Stephenson} always talked about outdoing Sebastian, outdoing Stephon,", and called him "The best I've ever had at Lincoln." Stephenson went on to lead the Railsplitters to the city title that year.
Lincoln High repeated as champions his sophomore and junior years, while Stephenson won back-to-back Player of the Year honors from the New York Daily News.
As a sophomore, he was the youngest player featured in the movie Gunnin' for That No. 1 Spot, which followed eight high school basketball prospects. In 2007 as a high school junior he was named to the annual USA Today's All-USA boys basketball team, the only non-senior to given that honor.
In July 2008, Stephenson tried out for the United States national team's under-18 team, but was cut because of chemistry reasons.
On February 15, 2009, Stephenson passed fellow Lincoln High School alumnus Telfair's previous record of 2,785 points in the Brooklyn borough title game to become the all-time leading scorer for high school basketball in New York State. In March 2009, Stephenson led Lincoln High to an unprecedented fourth consecutive Public Schools Athletic League (PSAL) class AA championship. Stephenson scored a game-high 24 points and grabbed 10 rebounds to in the 78–56 final win against John F. Kennedy, and helped Lincoln become the first school in city history to win four straight titles.
Stephenson's high school career ended in the New York State semifinal, where Rice High School beat Lincoln 77–50, and Stephenson was held to 12 points by Rice's Durand Scott, who also beat out Stephenson for the Daily News' New York City player of the year honor. He ended his career with 2,946 points.
In April 2009, Stephenson played in the McDonald's All-American Game, finishing with 12 points, six assists and three steals.
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