After playing sparingly for three seasons, he transferred to join the Hofstra Pride, where he led the Colonial Athletic Association (CAA) in scoring and was named second-team all-conference.
However, the coach left soon for Hofstra, where he told Upshaw the opportunity to play was even higher because four players had been kicked off the team after a burglary incident.
[20] After deciding to enter the 2016 NBA Development League Draft,[17] Upshaw was selected in the fourth round by the Grand Rapids Drive.
[22] On March 24, 2018, Upshaw scored 11 points in the regular-season finale to earn a playoff spot for Grand Rapids in a 101–99 home win over the Long Island Nets.
[28] Out of respect for Upshaw, the NBA G League delayed the first round of the 2018 playoffs,[29] while the Detroit Pistons gave him an honorary call-up to the team on March 29 for their game against the Washington Wizards.
[30] On May 30, 2018, Upshaw's parents filed a wrongful death lawsuit against the NBA, the Detroit Pistons, the SSJ Group, who owns the Grand Rapids Drive, and the DeltaPlex Arena.
[31] Afterwards, the Detroit Free Press reported that a year earlier, he had fainted and been diagnosed with hypertrophic cardiomyopathy, which is the chief cause of heart-related deaths of young athletes in the U.S. and which, combined with over-exertion, is believed to have killed him.