After four seasons at Dartmouth, James Blackwell went undrafted in the 1991 NBA Draft, despite averaging 19.3 points, 4.5 assists, three rebounds and 2.6 steals as a senior. From there, Blackwell would begin a long journey, which led him to the NBA after playing for eight different professional teams. During the 1994-95 NBA season, when Blackwell was 26 years old, the Charlotte Hornets took a chance on him, and he eventually earned an opportunity amid injuries.

Blackwell suited up in just four games for the Hornets, averaging one point, 1.3 assists and 0.8 rebounds. He'd latch on with the Celtics later in the year, playing in nine games for Boston. Unfortunately, that'd mark the end of Blackwell's NBA career; however, the former Ivy League point guard would carve out a successful career overseas, playing until the end of the 2001-02 season.