In his junior season, he led his team to a New York State Public High School Athletic Association (NYSPHSAA) Class AA championship while earning most valuable player (MVP) honors.

[1][2] He played for the Albany-based program City Rocks on the Amateur Athletic Union (AAU) circuit and was teammates with five-star recruit Isaiah Stewart.

[3] Playing for the City Rocks, Pickett led the Nike Elite Youth Basketball League in player efficiency.

After the season he declared for the 2019 NBA draft and participated in the G League Elite Camp but ultimately decided to return to Siena.

[12] He helped the team win the MAAC regular-season championship, averaging 15.1 points and a league-leading 6 assists per game while shooting 37.4 percent from three-point range.

[16] On February 14, 2023, Pickett scored a career-high 41 points in a 93–81 victory over Illinois, becoming Penn State's first 40-point scorer since 1961 and setting a Bryce Jordan Center record.

The two-game stat line was also only the third time over the last 25 seasons in NCAA Division I basketball or the NBA where a player scored 70-plus points, had 15-plus assists and 10-plus rebounds with a 65% field goal accuracy and 90% free-throw rate.