Garland played his high school basketball at Brentwood Academy in Tennessee, where he earned several prestigious accolades. Garland was named Mr. Basketball in the state of Tennessee three times, earning his way onto the USA Basketball junior national team in the process. He was a four-time state champion at Brentwood Academy, earning McDonald’s All-American honors, and appearing at the Nike Hoop Summit and Jordan Brand classic. ESPN and other recruiting analysts deemed him a five-star recruit and one of the players to watch in his recruiting class.

After being recruited by Duke and other college basketball powerhouses, Garland elected to go to Vanderbilt University in Nashville, Tennessee. Under head coach Bryce Drew, Garland was the most highly touted recruit to ever select Vanderbilt as their program of choice. The decision paid immediate dividends for Garland, whose non-conference schedule was highlighted by a 33-point performance against the Liberty Flames.

Unfortunately for Vanderbilt and Garland, he was unable to complete his freshman season due to a meniscus injury sustained in a game against Kent State. Garland never suited up for the Commodores again, as he announced in January of 2019 that he would be leaving the school to focus on rehabilitation and preparation for the upcoming NBA Draft.

The Cleveland Cavaliers selected Garland with the fifth overall pick in the 2019 NBA Draft. Garland was selected after the New Orleans Pelicans drafted Zion Williamson, the Memphis Grizzlies took Ja Morant, the New York Knicks selected RJ Barrett, and the Los Angeles Lakers took and traded De’Andre Hunter. He was drafted to play alongside Collin Sexton in the backcourt, with the plan being for the rookie Garland and second-year player in Sexton to be the foundation of the Cavaliers backcourt for the future against the Bucks, Bulls and Pacers in the Central division. Garland was signed shortly after the draft, along with fellow Cavs draft picks Dylan Windler and Kevin Porter Jr.

Garland’s rookie year was interrupted after the Cavaliers had played 65 games due to the coronavirus pandemic. Garland played in 59 of the team’s games, starting in all 59 of those contests. He averaged 12.3 points per game and 3.9 assists per game in nearly 31 minutes of action per contest. The rookie’s scoring average increased in each of his first four months in the league, peaking at 14.4 points per game in January of 2020.

Any rookie season comes with ups and downs, with Garland’s being no exception. Averaging five points per game in three games against the Boston Celtics and shooting 3-11 against the Clippers were certainly low points, but Garland has proven himself capable of getting the better of several elite teams as well. His 18 points on against the Denver Nuggets, or 50% shooting night against Russell Westbrook and the Houston Rockets were high points in his first year.