Portland Trail Blazers (2018–2025)
Simons was selected 24th overall by the Portland Trail Blazers in the 2018 NBA draft.[18] He would be the third high school player since 2015 to be drafted in the NBA, behind Thon Maker and Satnam Singh Bhamara. On July 2, 2018, the Trail Blazers announced that they had signed Simons.[19]
On January 21, 2019, the Blazers assigned Simons to the Agua Caliente Clippers for an NBA G League assignment.[20]
On April 10, 2019, Simons had his first career start against the Sacramento Kings while the Trail Blazers rested Damian Lillard and CJ McCollum for the final game of the regular season. Simons put up career highs across the board with 37 points, six rebounds, and nine assists, becoming the first Trail Blazers rookie to score 30-plus points since Lillard.
In the championship round of the Slam Dunk Contest during halftime of the 2021 NBA All-Star Game, Simons attempted to kiss the rim, but failed and still completed the dunk. Despite his failed attempt, Simons was named the 2021 Slam Dunk Champion on a 3–2 decision.[21]
On January 3, 2022, Simons scored a then career-high 43 points behind nine three-pointers, along with seven assists, in a 136–131 victory over the Atlanta Hawks. In a postgame interview, he dedicated the game to his grandfather who died of cancer the previous night.[22] On March 28, Simons was ruled out for the remainder of the season with patellar tendinopathy in his left knee.[23]
On July 6, 2022, Simons re-signed with the Trail Blazers on a four-year, $100 million contract.[24][25] On October 21, Simons hit a game-winning floater in a 113–111 overtime victory over the Phoenix Suns.[26] On December 3, Simons scored a career-high 45 points in a 116–111 win over the Utah Jazz.[27] On February 3, 2023, Simons scored 33 points in a 124–116 comeback win over the Washington Wizards.[28]
On October 25, 2023, Simons suffered a torn UCL in his right thumb against the Los Angeles Clippers, ruling him out for four to six weeks.[29]
On December 19, 2024, Simons had a double-double and hit the game-winning buzzer-beater against the Denver Nuggets.[30]