He is the younger brother of crosstown Horizon League foe and former George Westinghouse College Prep teammate David Bailey.
In head-to-head competition, Martell and the Flames defeated David and the Ramblers four out of five times, including a Horizon League men's basketball tournament championship game in which both were key performers.
As a senior, he played for the first high school basketball team to achieve a sellout at the United Center.
[2] As a junior, he moved up to the varsity team that was ranked 2nd in the city to King College Prep High School by the Chicago Sun-Times.
[6] The team reached the semifinals of the Chicago Public School League championships in 1999 with the two brothers starting and achieved a 31–1 record.
[8] That summer, Martell and Banks were named to the Amateur Athletic Union All-American team during the national junior boys championships.
[11] After David graduated, with Martell, Banks and Trammell, Westinghouse began the season as the top ranked team in the city by the Chicago Sun-Times in mid-November.
[11] As a result of the IHSA violation, it had to forfeit two of its three preseason weeks of practice, and coach Chris Head was suspended for November and December.
[13] He hit the game-winning shot with 3.3 seconds left to cap a comeback from an 8-point deficit with 2:50 remaining against the nationally ranked number one team, Oak Hill Academy, during the December 1999 Coca-Cola; KMOX Shootout at the Kiel Center.
[18][19] He was a first team All-State selection by the Illinois Basketball Coaches Association (along with Banks) and had a 3.7 GPA[1] The Chicago Sun-Times named Bailey and Banks to the Class AA All-State team that included Darius Miles, Eddy Curry, Dwyane Wade, T. J. Cummings, Roger Powell, Jr. and Jitim Young.
[26] Although the Bailey brothers played each other as Horizon League foes several times, the most notable was the 2002 Horizon League men's basketball tournament where the fifth-seeded Ramblers (17–12) and sixth-seeded Flames (19–13) opposed each other in the championship game for a 2002 NCAA Division I men's basketball tournament invitation with the entire family in attendance at the Cleveland State Convocation Center.
[30][35] Then, the 15th-seeded Flames played the 2nd-seeded Oklahoma Sooners, losing by a 71–63 margin to a team led by Hollis Price and Aaron McGhee.
[40] The team qualified for the 2003 National Invitation Tournament where they opposed the Western Michigan Broncos and fell by a 63–62 margin.
[45] Then the following season, he scored his career high on senior night with a 22-point performance during the 10th game of a winning streak against Butler on February 28, 2004.