Lee attended Pike High School in Indianapolis and played on their Indiana 4A state championship winning team in 2003. He starred for the Indy Hornet's AAU team, winning several state championships and annually placing high at the AAU nationals. Considered a three-star recruit by Rivals.com, Lee was listed as the No. 34 shooting guard in the nation in 2004.
College career
In 2004, Lee was recruited by former Western Kentucky assistant coachWilliam Small to play for the Hilltoppers. In his first season, Lee set a WKU record for freshman scoring with 461 points in 31 games. He was named First Team All-Sun Belt Conference for three consecutive seasons. As a senior at WKU, Lee was named Sun Belt Player of the Year. He also helped lead the Hilltoppers to a Sweet 16 appearance in the 2008 NCAA Tournament while being ranked 28th nationally in scoring with 20.4 points per game. On January 27, 2008, Lee recorded a career high 33 points in a 77–68 win over Arkansas State. Lee finished his collegiate career tied with Jim McDaniels for all-time leading scorer at WKU, with 2,238 points. During his four-year career at WKU, he started 128 games, played an overall 3,957 minutes, made 82% of free throws, made 245 three-point shots, had 242 steals, 281 assists and 78 blocked shots. On January 10, 2015, it was announced that Lee's jersey would be retired by the Hilltoppers. Lee's tattoo on his arm reads "R.I.P. Danny Rumph" dedicated to his WKU teammate who died in May 2005 from an enlarged heart after hitting a game winning shot in a pick-up game in his hometown, Philadelphia.
Professional career
Orlando Magic (2008–2009)
Lee was drafted 22nd overall by the Orlando Magic in the 2008 NBA draft. On February 4, 2009, Lee posted season-high numbers against the Los Angeles Clippers. He finished the night with 21 points, including 9-of-10 field goals while making three 3-pointers. Then on March 23, 2009 in a game against the New York Knicks at Madison Square Garden, Lee set a then-career high with 22 points. He made two critical free throws late in the fourth quarter to secure a comeback win for the Magic. Lee finished 6–8 from the field, 2–3 from behind the three-point line, and 8–8 from the free throw line. During the Magic's first round NBA playoff series against the Philadelphia 76ers, Lee scored 18 points in game 1 and a team-high 24 points in game 2, helping the team tie the series at 1–1. On April 28, 2009 Lee was hit in the face by Dwight Howard during Game 5 of the Magic's first round playoff series, suffering a fractured sinus. The following day it was announced that he would miss Game 6 of the series due to the injury. He then returned for the second round matchup against the Boston Celtics but he was forced to wear a protective mask over his face for the remainder of the postseason. In game 2 of the 2009 NBA Finals, Lee missed a potential game-winning layup with 0.6 seconds remaining on the shot-clock at the end of regulation that would have evened the series at 1.
On August 11, 2010, Lee was traded to the Houston Rockets in a four-team, five-player trade in which the Rockets sent Trevor Ariza to the New Orleans Hornets. He was officially introduced by the Rockets on August 18, 2010.
Boston Celtics (2012–2014)
On July 20, 2012, Lee was traded to the Boston Celtics in a three team sign and trade deal involving the Houston Rockets and Portland Trail Blazers. Lee agreed to a 4-year, $21.5 million deal with Boston. He had a fine start to the 2013–14 season hitting around 50 percent of his 3-point attempts under new coach Brad Stevens.
Memphis Grizzlies (2014–2016)
On January 7, 2014, a three-team trade was completed between the Celtics, the Memphis Grizzlies, and the Oklahoma City Thunder. Boston traded Lee and a 2016 second round draft pick to Memphis for in exchange for the Grizzlies' Jerryd Bayless and the Thunder's Ryan Gomes.
On February 16, 2016, the Grizzlies traded Lee to the Charlotte Hornets in a three-team trade also involving the Miami Heat. Five days later, he made his debut and first start with the Hornets in a 104–96 win over the Brooklyn Nets, recording five points, one rebound and one assist in 21 minutes.
On July 8, 2016, Lee signed with the New York Knicks. Prior to the start of the 2017–18 season, Lee was named co-captain of the Knicks alongside Lance Thomas. On January 15, 2018, in a 119–104 win over the Brooklyn Nets, Lee made his 44th straight free throw on a third-quarter technical, tying the Knicks' record set by Chris Duhon in 2008–09. Lee came into the game leading the league at 96.1 percent after hitting 73 of 76. Two days later, he converted a free throw in the second quarter of the Knicks' 105–99 loss to the Memphis Grizzlies—his 45th straight, setting a franchise record. In December 2018, he played a game with the Knicks' NBA G League affiliate, the Westchester Knicks.