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Dennis Rodman won two titles with the Detroit Pistons in 1989 and 1990. Then he won three more with the Chicago Bulls in 1996, 1997, and 1998.
Five. Two with the Pistons (1989, 1990) and three with the Bulls (1996, 1997, 1998).
No, he was traded to the Chicago Bulls in 1996 for Will Purdue. The San Antonio Spurs won their first championship in 1999.
San Antonio Spurs
Rodman's first season with the Bulls was the 1995-96 season. He spent three seasons with them and they won the NBA championship each season.