Derrick played his high school ball at Simeon Career Academy. There, Derrick began making a name for himself throughout the Chicago area and eventually on a national level. He led Simeon to back to back championships; a feat that had never been done before by a public school team in Chicago. In his senior year, Derrick carried his team past then #1 ranked Oak Hill Academy scoring 29 points, dishing out 9 assists and grabbing 8 rebounds. It was Oak Hills’s sole loss on the year. For his effort against the nation’s top team, Derrick was named USA Today’s national high school player of the week. After a senior season in which he averaged 25.2 points, 9.1 rebounds, 8.8 assists and 3.4 steals, Derrick was named Illinois Mr. Basketball. On the left front tail is the “Nike” manufacturers tag with jersey size “XXL.” Written in blue marker is “06 D. Rose” indicating jersey year and player name, respectively. Across the front is “SIMEON.” Player number “25” appears on both the front and back. All numbers and letters are done in yellow on white tackle twill. Above the player number on back is “ROSE” written in black marker where the player name would typically be embroidered. There is a large team repair as a part of the player name. On the back number “2” is “Poohdini #1 Gm. Worn H.S. State Champs 06” written in black marker along with an autograph which rates a 7-8. On front below the player number is a large autograph also done in black marker rating an 8-9. The jersey shows game-use and is accompanied by a LOA from JSA.