Pippen recalled having an awkward first interaction with MJ.

Scottie Pippen and Michael Jordan Won 6 NBA Championships Together, but Their Relationship Didn't Exactly Start on the Right Foot: 'Michael Was a Little Distant' - Sportscasting | Pure Sports
The success Michael Jordan and Scottie Pippen had with the Chicago Bulls, leading them to six championships, often creates the misconception that the relationship between them was always great. In fact, the two got off to a shaky start.

Interestingly, “His Airness,” driven by motivation to win at all costs, wasn’t too optimistic about Scottie joining the team. This led to an awkward first interaction between them.

Pippen on his awkward first interaction with MJ
Unlike Jordan, who entered the NBA as an NCAA champion and an Olympic gold medalist, Pippen didn’t join the Bulls with so much fanfare. The fact that he came out of the University of Arkansas, which wasn’t a basketball powerhouse, had something to do with that.

Pete Myers, a 6’6″ shooting guard who played in Chicago during the 1986-87 season, gave another reason for MJ to be skeptical about Pippen.

“His Airness” thought Myers, who averaged only 2.3 points over 29 games for the Bulls, was also from Arkansas. And even though he was wrong, Mike had his reservations about another guy from the same program joining the squad.

“Michael was a little distant. He was more … he was competitive; that was kind of his drive in those days,” Pippen recalled. “I remember Michael said, ‘Well, we got another one of those Arkansas boys’ when I was drafted. Knowing the Bulls had drafted Pete Myers, he was an Arkansas kid, from the University of Arkansas (at Little Rock). He was actually from Mobile, Alabama. That’s kind of all I remember.”

Pippen didn’t take long to prove his worth
Pippen took that challenge head-on to show everyone, including Michael, just how good he was. Even coming off the bench, averaging 20.9 minutes per game, he made a strong impression in his rookie season, putting up 7.9 points, 3.8 rebounds, and 1.2 steals per contest.

Scottie became a starter in the playoffs and increased his output to 10.0 points and 5.8 rebounds per outing. After that, he established himself as the perfect sidekick next to the greatest player ever.