His father's relationship with his mother, Larsa Pippen, led to three future younger full siblings: Preston, Justin, and Sophia.

From kindergarten to tenth grade, Scotty attended Pine Crest School in Florida where he gave his first post game interview as a sophomore.

Before his junior year,[citation needed] his family moved to the LA area and he transferred to Sierra Canyon School in Chatsworth, California which had a more competitive basketball team.

At Sierra, he played alongside future NBA players such as Marvin Bagley III, Kenyon Martin Jr., and Cassius Stanley.

[2] As a senior, he averaged 16.3 points, 4.6 assists, and 3.6 rebounds per game and helped his team win the California Interscholastic Federation Open Division state title.

[8] As a freshman, Pippen averaged 12 points and 3.6 rebounds per game, earning Southeastern Conference (SEC) All-Freshman Team honors.

[18] In his Summer League debut, Pippen scored fourteen points, six rebounds, three assists, and a block in a 100–66 win over the Miami Heat.

[26] On November 8, Pippen recorded his first career triple-double with 11 points, 10 rebounds, and 11 assists in a 128–104 win over the Washington Wizards.