In his last four games with the Detroit Pistons, 27-year-old Milton (6-5, 205 pounds) averaged 6.8 points, 4.5 rebounds, and 1.5 assists in 15.8 minutes of play. Milton played in 38 games with the Minnesota Timberwolves at the start of the 2023–24 season before being acquired by Detroit. In 12.9 minutes, he averaged 4.7 points, 1.3 rebounds, and 1.3 assists.
Against Memphis on December 8, 2023, he recorded a career-high 17 points on 66.7 percent shooting, two rebounds, and one assist in addition to shooting 60 percent from the three-point line. Before Minnesota,With the Philadelphia 76ers for five seasons, Milton played in 254 games (45 starts), averaging 9.3 points, 2.7 assists, and 2.4 rebounds in 20.8 minutes.
He finished 12th in the Sixth Man of the Year voting in the 2020–21 season after recording a career-high 13.1 points, 3.1 assists, and 2.3 rebounds in 23.2 minutes in 63 games (four starts). Throughout the course of his six seasons with the Sixers, Timberwolves, and Pistons, Milton has averaged 8.7 points, 2.5 assists, and 2.3 rebounds while playing 19.7 minutes in 296 games (45 starts).
The Dallas Mavericks originally picked the Owasso, Oklahoma native with the 54th overall choice in the 2018 NBA Draft, after he was selected out of SMU. He averaged 18.0 points, 4.7 rebounds, 4.4 assists, and 1.4 steals in 22 games (all starts) as a junior, earning him a spot on the Second Team All-AAC. In addition, he was selected First-Team Parade All-American, First-Team All-Rookie team, and Second-Team All-AAC as a sophomore. Milton played in 87 games (80 starts) throughout three seasons at SMU, averaging 13.4 points, 3.9 rebounds, and 3.9 assists in 34.7 minutes per game.