Eaglestaff grew up in Mandan, North Dakota and attended Bismarck High School.[3][4] As a senior he averaged 30.3 points and 8.3 rebounds per game and would earn first team All-State honors for the second year in a row.[5][6] During his senior year he would also be named North Dakota Mr. Basketball, the first person from his high school to ever do so.[7] On July 5, 2021, Eaglestaff would announce his commitment to play basketball for North Dakota.[8] He also received an offer from Abilene Christian.[9]
College career
As a freshman, Eaglestaff would play in 33 games and start in 11 of them. He would average 8.4 points, 2.5 rebounds, and 1.7 assists per game. As a sophomore he would start in all 32 of North Dakota's games, averaging 14.4 points, 2.3 rebounds, and 1.5 assists per game.[10]
During the 2024–25 season, Eaglestaff would make national headlines after scoring 40 points against No. 6 Alabama, becoming the first mid-major player to score 40 points against an AP-Top 10 opponent since 2012.[11][12][13]