Armstrong was born in Gastonia, North Carolina and graduated from Ashbrook High School of Gastonia in 1986. At Ashbrook, Armstrong was a punter and wide receiver on the football team and began playing basketball as a senior. Armstrong then attended Fayetteville State University, a Division II college in Fayetteville, North Carolina and part of the Central Intercollegiate Athletic Association (CIAA) conference, and joined the football team as a walk-on placekicker. Armstrong played football for the 1986 and 1987 seasons and twice kicked school-record 48-yard field goals. In 1988, Armstrong joined the Fayetteville State basketball team and would play three seasons under coach Jeff Capel II. In his senior season of 1990–91, Armstrong played 24 games and averaged 16.4 points, 3.6 rebounds, and 4.7 assists. Armstrong was the CIAA Slam Dunk champion in 1990 and a first-team All-CIAA selection in 1991.\n', '

Armstrong was not selected in the 1991 NBA draft and began his career with the Atlanta Eagles (renamed Trojans in 1994) of the United States Basketball League (USBL) in 1991. Armstrong was named to the USBL All-Defensive team three consecutive seasons from 1992 to 1994, was a second-team All-USBL selection in 1992, and first-team All-USBL selection in 1993 and 1994.\n', '

In October 1992, Armstrong signed with the Capital Region Pontiacs of the Continental Basketball Association (CBA). Armstrong later played for the South Georgia Blues of the Global Basketball Association until the team folded in 1993. After playing for the Blues, Armstrong returned to Gastonia. He volunteered at Ashbrook High School as an assistant basketball coach and worked the night shift at a yarn factory.\n', '

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