Chicago's GM Jerry Krause and the team's head coach Phil Jackson met with Dennis for 36 hours before pulling the trigger on the deal. Ultimately, Phil was the one who made the decision to go through with the trade and acquire the league's most controversial personality.
I got to know a little about Dennis, that he’s overcome a lot of odds. He’s an awful strong individual and I’m confident he will take himself out of situations that have been tough for him his whole life.
Phil Jackson, Washington Post
The move was made with the approval of the Bulls superstars Michael Jordan and Scottie Pippen, who were ready to look past the persona Rodman represented -- Phil described him as "extremely individualistic." Off the court, Dennis wanted to have freedom and the expression that gives, and as long as that didn't interfere with the team on the court, the Bulls were OK with it. What Rodman said after joining the team only made them even more confident that would be the case.
I think I'm just part of the components that run this computer, that's it.
Jordan, in particular, was very excited to play with Rodman. Personality aside, he knew what the 34-year-old would bring to the table basketball-wise. Coming off his first retirement, Mike felt re-energized to once again embark on a quest for multiple NBA championships. He felt Rodman, "one of the most dominant players in basketball," was just the right guy to do it with.
Very few players are making All-Star teams off of defense and rebounds. Scottie and I talk about it all the time; we sit down, we watch him and it's like, 'it's good to have him on our team instead of facing him.' He is by far the best rebounder I've ever seen. He doesn't have the oversized physique to help him in that; it's just his heart and desire and the ability to go get the ball.
You know how the rest of the story goes; the Bulls won their second three-peat, with Rodman being a crucial component of the greatest computer in NBA history. Everything MJ said about him, the 6-7 forward displayed on the court, becoming the team's most valuable contributor outside their iconic duo.
He still had his antics which would've had him fired on any other NBA team. But the Bulls were able to look past it. What they got in return made their effort worthwhile. And MJ knew that would be the case from the moment they acquired The Worm.