Highsmith was born in Baltimore and played college basketball for Wheeling Jesuit University where he was named NCAA Division II Player of The Year in 2018. After not being selected in the NBA Draft, Highsmith began his professional basketball career with the Delaware Blue Coats of the NBA G League in 2018. Late in the 2018–19 season, Highsmith made his NBA debut with the Blue Coats' parent team Philadelphia 76ers. In later years, Highsmith played in multiple stints with the Blue Coats, and the Crailsheim Merlins of the German Basketball Bundesliga. In February of 2022, Highsmith signed a 3 year contract with the Miami Heat.

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