Growing up in Hamilton, he did not make the St. Thomas More junior team in grade 9 and subsequently played on the school's midget squad. He ended up winning team MVP and the midget boys' city championship. He then attended Sir Allan MacNab Secondary School before heading to Hamilton Heights Christian Academy in Chattanooga, Tennessee in 2015. "I just thought I needed to play better competition...," he said. As a senior, Gilgeous-Alexander averaged 18.4 points, 4.4 rebounds and 4.0 assists. In early 2016, he participated in the Basketball Without Borders Camp. A four-star recruit, Gilgeous-Alexander originally committed to Florida, but re-opened his recruitment in October 2016. His final five schools were Kentucky, Kansas, Syracuse, Texas and UNLV. The following month, he announced his decision to play college basketball at Kentucky. At the 2017 Nike Hoop Summit, he poured in eleven points in 21:24 minutes of action, representing the World Select Team.
College career
Shai Gilgeous-Alexander started the 2017-18 season as a reserve, sitting behind freshman point guard Quade Green, but still averaged over 30 minutes per game. After a tough loss to UCLA, Alexander erupted against Louisville in December, scoring 24 points, grabbing 5 rebounds, dishing out 4 assists, and securing 3 steals. When he first stepped on the University of Kentucky's campus, Gilgeous-Alexander had long hair. However, he cut his hair early in the season and some say this started his progression from sixth man to starting point guard. He continued to lead the team for the following two games against Georgia and LSU, scoring 21 points against Georgia and 18 against LSU. He was a consistent contributor to a "struggling" UK team that had a four game losing streak during the season. He became a starter along with four other freshmen: Hamidou Diallo, Nick Richards, Kevin Knox, and P. J. Washington. Despite their losses, his PPG shot up to 12.9 along with 3.8 rebounds and 4.6 assists. Gilgeous-Alexander had a great SEC tournament and continued that momentum into the NCAA Tournament. After playing great basketball in the first two rounds against Davidson and Buffalo, the magic ran out and Kentucky lost to Kansas State in the Sweet 16. Gilgeous-Alexander's final college basketball moment was a missed three-point attempt at the buzzer. On April 9, 2018, he declared for the 2018 NBA Draft.
Professional career
Los Angeles Clippers (2018–2019)
On June 21, 2018, Gilgeous-Alexander was selected with the eleventh overall pick by the Charlotte Hornets in the 2018 NBA draft, before being traded to the Los Angeles Clippers the same day, in exchange for the pick after him and two future second round picks. He went on the play for the team in the 2018 NBA Summer League, where he averaged 19 points, 4.8 rebounds, 4 assists and 2.3 steals per game. On December 17, 2018, Gilgeous-Alexander scored a season-best of 24 points in a 127–131 loss to the Portland Trail Blazers. On January 18, 2019, Gilgeous-Alexander tied his season-best of 24 points in a 94–112 loss to the Golden State Warriors. Eleven days later, he was named a member of the World Team for the 2019 Rising Stars Challenge. On April 21, 2019, he scored a new career-high of 25 points in a 105–113 loss to the Golden State Warriors in game 4 of the 2019 playoffs.
Oklahoma City Thunder (2019–present)
On July 10, 2019, the Clippers traded Gilgeous-Alexander, Danilo Gallinari, five first-round draft picks, and the rights to swap two other first round picks to the Oklahoma City Thunder for NBA All-Star Paul George. On October 8, 2019, Gilgeous-Alexander made his preseason debut with the Oklahoma City Thunder against the Dallas Mavericks. He recorded 24 points, 4 rebounds and 1 assist in a 119–104 win over the Mavericks. On December 22, 2019, Gilgeous-Alexander scored a career-high 32 points with five assists, three rebounds, and two steals in a 118–112 win over the Los Angeles Clippers. On January 13, 2020, Gilgeous-Alexander recorded his first NBA triple double with 20 points, 10 assists and a career-high 20 rebounds in a 117–104 win over the Minnesota Timberwolves, becoming the second player after Russell Westbrook to record a 20–20–10 statline in the last 30 years and the youngest ever to achieve it. In July 2020 he signed an endorsement contract with Converse
Gilgeous-Alexander's younger brother, Thomasi Gilgeous-Alexander, is a college basketball player for the Evansville Purple Aces. His younger cousin, Nickeil Alexander-Walker, is an NBA rookie for the New Orleans Pelicans. The two have a close relationship and shared a room at high school coach Zach Ferrell's house.