After high school, Highsmith attended Wheeling Jesuit University (now Wheeling University) and played four seasons for the Wheeling Jesuit Cardinals from 2014 to 2018. He became a starter for the team towards the end of his freshman season. He averaged 14.5 points and 9.4 rebounds as a sophomore, his first full year as a starter, and was named first team All-Mountain East Conference (MEC).[3] In his junior season, Highsmith averaged 15.3 points and 10.8 rebounds and was named second- team All-MEC.[4] As a senior, Highsmith averaged 22 points and 12.6 rebounds per game and was named first-team All-MEC, MEC Player of the Year, and the MVP of the MEC Conference tournament. Nationally, he was named first-team Division II All-America by the National Association of Basketball Coaches and the National Player of the Year by the Division II Conference Commissioner's Association.[5]
Highsmith was signed to a two-way contract by the Philadelphia 76ers on January 8, 2019. Under the terms of the deal, he split time between the 76ers and the Blue Coats.[7] Highsmith made his NBA debut the same day, scoring three points in five minutes of play in a 132–115 win over the Washington Wizards, after also playing in a game for the Blue Coats against Raptors 905 earlier in the day.[8] Highsmith finished his first professional season averaging 1.8 points and one rebound over five NBA games and 12.2 points, 6.8 rebounds , 2.5 assists, and 1.2 steals over 46 G League games (42 starts).[9]
After his Exhibit 10 deal with the Phoenix Suns fell through,[11] Highsmith returned to the 76ers to sign an Exhibit 10 contract.[12]
Highsmith re-joined the Blue Coats for the 2019–20 season.[13] On December 31, Highsmith posted 20 points, eight rebounds, one assist and one steal in a loss to the Maine Red Claws.[14] He averaged 10.8 points and 6.9 rebounds per game.[15]
On July 27, 2021, Highsmith signed with Vanoli Cremona of the Italian Lega Basket Serie A (LBA)[17] with an NBA exit option. As an Exhibit 10 offer arrived from the Philadelphia 76ers, he decided to withdraw from Cremona and return to the U.S.[18] On September 30, he signed and was waived by the 76ers.[19]
Highsmith rejoined the Blue Coats in 2021. He averaged 14.0 points, 5.0 rebounds, and 1.9 assists per game.[20]
Miami Heat (2021–2022)
On December 30, 2021, Highsmith signed a 10-day contract with the Miami Heat via the hardship exemption.[20]
On February 15, 2022, Highsmith signed a standard 10-day contract with the Miami Heat.[22] Ten days later, he signed a second 10-day contract.[23] Following the expiration of the second 10-day contract, Highsmith signed a three-year deal to remain with the Heat.[24][25]
On December 20, 2022, Highsmith scored a career-high 18 points, alongside two rebounds, two assists and four steals, in a 113–103 loss to the Chicago Bulls.[26] The Heat qualified for the play-in tournament and advanced to face the top-seeded Milwaukee Bucks in the first round, whom they defeated in five games in a historic upset.[27] In game 5 of the Eastern Conference Finals, Highsmith scored a then-playoff career-high 15 points, alongside two rebounds and two steals, in a 110–97 loss to the Boston Celtics.[28] The Heat eventually defeated the Celtics in seven games to advance to the 2023 edition of the NBA Finals against the Denver Nuggets. In game 1 of the Finals, Highsmith matched his career high of 18 points, alongside two rebounds and two steals, in a 104–93 loss.[29] The Heat went on to lose the series in five games.
On July 8, 2024, Highsmith re-signed with the Heat.[30]
