
A top ranked prospect out of Lake Oswego High School in Oregon, Love played one season of college basketball for the UCLA Bruins and led the team to a Final Four appearance in the 2008 NCAA Tournament. Love was named a consensus First Team All-American and was voted the player of the year in the Pac-12 Conference. He elected to forego his remaining three years of college eligibility and entered the 2008 NBA draft. He was taken fifth overall by the Memphis Grizzlies, and was traded to the Minnesota Timberwolves on draft night for the third overall selection, O. J. Mayo, in an eight-player deal. Love was traded to the Cavaliers in 2014.

The Cavaliers finished the regular season as the first seed in the Eastern Conference with a 57–25 record. In the first round of the playoffs, the Cavaliers faced the eighth-seeded Detroit Pistons, and in a Game 1 win on April 17, Love recorded playoff career highs with 28 points and 13 rebounds. Love helped the Cavaliers advance through to the Eastern Conference Finals where they faced the Toronto Raptors. He struggled in Games 3 and 4 of the series, scoring just 15 total points, before bouncing back in Games 5 and 6 to help the Cavaliers defeat the Raptors 4–2 and advance through to the NBA Finals.