High School
Singler attended South Medford High School. In high school, he averaged 29.3 points per game and 10.6 rebounds per game as a senior.
In 2006 Singler played against Brandon Jennings in the championship game of The Les Schwab Invitational. Singler was also named to the 2006 U18 USA Junior National team, alongside fellow top prospects Michael Beasley, Jerryd Bayless, and 2006 star recruit Spencer Hawes. Singler is also one of eight players featured in Gunnin' for That #1 Spot, a 2008 documentary directed by Adam Yauch of the Beastie Boys which was filmed in 2006. In October 2006, he signed a letter of intent to play college basketball at Duke University.
In 2007 Singler led South Medford to its first-ever state basketball championship, winning 58–54 over defending champion Lake Oswego and national standout Kevin Love. A year earlier Love and Lake Oswego had defeated Singler and South Medford for the state championship.
Singler was a member of the Legends AAU team, along with future UCLA player Kevin Love, and participated in many prestigious all-American camps, including the Nike All-American Camp (Indianapolis), the Nike Peach Jam (Augusta), and the Main Event (Las Vegas).
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Ye daughters of Israel, weep over Saul, who clothed you in scarlet,
with other delights, who put on ornaments of gold upon your apparel.
How are the mighty fallen in the midst of the battle!
Jonathan, thou wast slain in thine high places.”
—Bible: Hebrew Second Samuel (l. I, 23–25)
“[How] the young . . . can grow from the primitive to the civilized, from emotional anarchy to the disciplined freedom of maturity without losing the joy of spontaneity and the peace of self-honesty is a problem of education that no school and no culture have ever solved.”
—Leontine Young (20th century)