The COVID19-shortened 2019-20 season was Valentine's third season in the Association. He appeared in 36 games for the Bulls, out of a possible 65, during the season. Valentine averaged 6.8 points, 2.1 rebounds and 1.2 assists in 13.6 minutes per contest. He shot 40.9 percent from the field and drained 1.3 three-pointers per game at a 33.6 percent clip. Arguably his best overall performance of the campaign was Dec. 11 against the Hawks. In 22 minutes, Valentine posted 10 points (4-8 FG, 0-3 3Pt, 2-2 FT), five assists, four steals, three rebounds and two blocks. On Mar. 2, the versatile wing scored a season-high 17 points during a home win over the Mavericks. For the season, Valentine posted double-digit points 12 times and grabbed at least three rebounds 12 times. He had multiple steals in five games. In the eight games that Valentine saw at least 20 minutes, he averaged 12.1 points, 2.9 rebounds, 2.4 assists and 1.8 steals. He also averaged 1.8 made threes in those games. In October and November, Valentine missed 14 of Chicago's first 17 games due to ankle and hip injuries.2018
Despite a stellar sophomore season, Valentine battled ankle trouble through the entirety of October and remained out indefinitely in early-November. It was announced Nov. 19 that he would undergo ankle surgery, which was originally given a 4-to-6 week timetable. Valentine ended up needed a more serious stabilization procedure, and before the end of November, the Bulls announced he would miss the entirety of the 2018-19 season. After a summer of recovery, Valentine was deemed "ready to go" for the 2019-20 season.2017
Valentine appeared in 77 games (37 starts) during the 2017-18 campaign with the Bulls. He set career highs in points (10.2), rebounds (5.1) and assists (3.2) per game. He also set highs in field-goal percentage (41.7) and three-point percentage (38.6). He set single-game career highs in points (34), rebounds (13), assists (seven) and steals (five). Valentine's best performance of the season occurred Mar. 17 during a five-point loss to the Cavaliers. He started, played 39 minutes and posted 34 points (13-20 FG, 8-11 3Pt), seven rebounds, six assists and one block. It was one of his four games with at least 20 points. He also ended up with five double-doubles on the season. Valentine also had the third-highest VORP (0.5) on the Bulls of anyone who saw at least 1,000 minutes with the team. The Bulls finished the season 27-55 and did not make the playoffs.2016
Following four seasons at Michigan State, Valentine was selected with the 14th overall pick in the 2016 NBA Draft by the Bulls. He made his NBA debut during the second game of the season, Oct. 29 during a 17-point win over the Pacers. Valentine saw five minutes of run and posted one rebound. Valentine ultimately appeared in 57 games. Across 17.1 minutes per contest, Valentine averaged 5.1 points, 2.6 rebounds and 1.1 assists. He shot 35.4 percent from the field and 77.8 percent from the charity stripe. The rookie drained 1.3 three-pointers per contest and shot 35.1 percent from behind the arc. Valentine set single-game career highs of 19 points, 12 rebounds, five assists, three steals and two blocks. On Jan. 10, the rookie scored a season-high 19 points during a close loss at Washington. His best performance of the season occurred Feb. 24 during a seven-point victory over the Suns. Valentine posted 15 points (5-9 FG, 5-8 3Pt), five rebounds, five assists and three steals in 34 minutes. On Mar. 18, Valentine recorded his first career double-double with 11 points and 12 rebounds during a home win over the Jazz. The Bulls finished the season 41-41, making the playoffs but losing in the Eastern Conference First Round to the Celtics in six games. Valentine played 22 playoff minutes, totaling five points, eight rebounds, two assists and one block. During the season, Valentine missed games due to recurring ankle injuries.
June 23, 2016Drafted by the Chicago Bulls in the 1st round (14th pick) of the 2016 NBA Draft.
July 16, 2016Signed a rookie contract with the Chicago Bulls.
November 21, 2020Signed a one-year, $4.7 million qualifying offer with the Bulls.