Chicago Bulls

Selected by the Chicago Bulls in the first round of the 1989 NBA draft,^[1] the 6'2" (1.88 m) Armstrong helped the team return to the Eastern Conference Finals after compiling 55 regular season victories in 1990.^[2]

In 1991, he helped them win their first NBA title against the Los Angeles Lakers after winning 61 games. In 1992, Armstrong averaged double-digit scoring while coming off the bench behind longtime starter John Paxson to help the Bulls win 67 games and their second straight title. In 1993, he locked down the starting job, contributing to a 57–25 record and the Bulls' third straight title. He also claimed the NBA's three-point field goal percentage crown with a mark of .453 on 63-for-139 shooting.^[3]

In 1994, he emerged as more of a leader in the wake of Michael Jordan's abrupt retirement, placing third on the team in scoring. He was voted a starter in the 1994 NBA All-Star Game, finished second in the NBA in three-point field goal percentage at .444 while leading the team to a 55–27 record and a second-round exit from the playoffs.

Armstrong finished third in scoring again in 1995 as the Bulls posted a 47–35 record, and with Jordan, Scottie Pippen and Toni Kukoč, led the team to the second round again.

Golden State Warriors

Armstrong was the first player chosen in the 1995 NBA Expansion Draft (via Toronto Raptors) but refused to report. He was traded by the Raptors to the Golden State Warriors in exchange for Carlos Rogers and 4 other players and played for the Warriors in 1996 and in 1997.

Charlotte Hornets

Four games into the 1997–98 season, Armstrong was acquired by the Charlotte Hornets for Tony Delk and Muggsy Bogues, playing 62 games that year. He also played 10 games for the Hornets in the 1999 season before being traded to the Los Angeles Lakers, alongside J.R. Reid and Glen Rice, for Elden Campbell and Eddie Jones. The Lakers immediately waived Armstrong, and he signed by the Orlando Magic in March of that year.

Orlando Magic

Armstrong was signed by the Orlando Magic in March of the 1998–99 NBA season.

Return to Chicago

On August 30, 1999, he was again signed by the Bulls and played the 1999–2000 season and retired at the end of the season, ending his career with the team that drafted him and with which he spent much of his playing career.