Entering the 1988-89 season, the Pistons were battle tested and hungry. They had spent the last few years battling the Bulls and Celtics, and were coming off a 4-3 loss to the Lakers in the NBA Finals. As the Pistons were set to resume the season after the All-Star break, Jack McCloskey pulled the trigger on a surprise trade, sending fan favorite Adrian Dantley to Dallas for Mark Aguirre, coincidently the number one pick in the 1981 NBA Draft. The Pistons finished the season with a team-record 63 wins, including an astounding record of 30-4 after the Aguirre-for-Dantley trade.

The Pistons faced the Boston Celtics in the first round. This would be the fourth time in five seasons that the two teams met in the post-season. Not only was there a hatred amongst the teams on the court, but the venom spread to the pages of newspapers and magazines. Both Celtics play-by-play man Johnny Most and team President Red Auerbach said that the Pistons were classless bullies. Their words, however, did not stop the Pistons, who swept the Celtics in three games. Next up: the Milwaukee Bucks.