The Bulls were on the verge of being eliminated in the
1988 Eastern Conference Semifinals by the
Detroit Pistons and the team had won just four total playoff games – and sported a 4-15 playoff record – in the first four seasons with Michael Jordan. There was a large dividing line among Bulls management that led to a theory that the team would
"never win a title because Jordan’s style of one-on-one play eliminated the other players as contributors." But this is where Reinsdorf comes in, as he was somewhat hurting for money. Jordan brought in the fans, the fans paid for merchandise, and Reinsdorf obviously loved that aspect. With the news of possibly moving the White Sox to Florida coming out, moving Jordan would probably mean Chicagoans calling for his head and demanding nothing less. Yet, even still,
Reinsdorf’s discussions with Florida could mean he didn’t care about any of that. Bulls head coach Doug Collins had also informed Reinsdorf that the team
"couldn’t win with Jordan." The writing seemed on the wall that Jordan would have to be gone.