After playing with the Expos minor-league affiliate Harrisburg Senators, Lee was traded to the Cleveland Indians and went to the major leagues later that season. He was traded to the Phillies in 2009, then traded to the Seattle Mariners and Texas Rangers, and returned to the Phillies as a free agent in 2011. A four-time All-Star, Lee won the American League Cy Young Award in 2008 as a member of the Indians after he led the American League in wins and lowest earned run average (ERA). Lee won his first straight seven postseason starts; as a Phillie going 4-0 in the 2009 postseason including pitching a complete game in 2009 World Series against New York Yankees, and next season with the Rangers where he shutout the Yankees 8-0 in the 2010 ALCS en route to reaching the 2010 World Series.
Lee is left-handed and threw three fastballs: a four-seam, two-seam and cutter. His pitches also included a slider, curveball and change-up.
Lee was drafted by the Florida Marlins as the twelfth pick of the eighth round of the 1997 Major League Baseball draft out of Benton High School in his hometown of Benton, Arkansas, but instead chose to attend Meridian Community College in Mississippi. Later, Lee was drafted by the Baltimore Orioles in the twentieth round of the 1998 amateur draft, but opted to attend the University of Arkansas instead.
In the 2000 major league draft, he was chosen in the fourth round by the Montreal Expos and signed in July of that year. In 2002, Lee played for Double-A Harrisburg, and compiled a 7–2 record with a 3.23 ERA in the Eastern League by mid-summer.
In June 2002, the Expos traded Lee (along with Brandon Phillips, Lee Stevens, and Grady Sizemore) to the Cleveland Indians in exchange for Bartolo Colón and Tim Drew.
Following the trade, Lee pitched seven games with the Akron Aeros before he went to the Buffalo Bisons. He compiled a 3–2 record with the Bisons before going to the Indians in September of that season. Lee made his major league debut in a start against the Minnesota Twins on September 15, 2002, giving up a lone run in 5.1 innings, resulting in a loss due to lack of run support. He pitched once more that season, giving up one run in five innings against the Kansas City Royals, resulting in a no decision for Lee but a loss for the team.
Lee won at least fourteen games in each of his first three full seasons and pitched more than 200 innings in both 2005 and 2006. He finished the 2005 season with an 18–5 record and a 3.79 ERA, earning him fourth place in the AL Cy Young Award voting that year. In 2006, the Indians gave him a midseason 3-year $14 million contract extension.
In 2007, Lee suffered a groin strain during a spring training start, forcing him to begin the regular season on the disabled list. He returned to the Indians' pitching rotation in May, but got only a 4–9 record and a 5.38 ERA in his first 16 starts. On July 21, Lee hit Texas Rangers' right fielder Sammy Sosa in the head with a pitch on the night when the Rangers were honoring Sosa for hitting his 600th home run. The incident sparked an altercation between Lee and Indians' catcher Víctor Martínez and led to a players-only meeting immediately after the game. Lee encountered more problems on July 26, 2007, when he gave up seven runs in four innings against the Boston Red Sox. When he left the game, the fans booed him and he tipped his cap to the fans before he entered the dugout. The next day, on July 27, Lee was optioned to Triple-A Buffalo Bisons. He was called back up on September 1 when rosters expanded, but only appeared in four games, all out of the bullpen.
In 2008, Lee had a career year. Despite the Indians playing with a .500 winning percentage for the season, Lee started the 2008 season with much success. Lee was one of only eight pitchers since 1920 to win 19 or more of his first 21 games. He was the first Cleveland pitcher to win his first six starts since Greg Swindell in 1988. He also recorded his first career shutout on April 25, 2008, against the Kansas City Royals, allowing just three hits and no walks. He had the lowest On-base percentage since 1909, having only a .163 percentage through five starts. For his efforts and success, he was named the American League Pitcher of the Month for April, when he went 5–0 with a 0.96 ERA. Lee was picked to his first All-Star game in 2008, and was also selected to start the game. Lee pitched two scoreless innings for the American League team, striking out three batters and giving up only a Chipper Jones base hit.
On August 26, Lee won his 19th game of the season, yielding only two runs to the Detroit Tigers. This victory set a new career high for Lee, outdoing his previous mark of 18 wins during the 2005 season. On September 1, Lee won his 20th game of the season, where he pitched a shutout. He was the first Indian to earn 20 wins since Gaylord Perry in 1974. In August, Lee was named American League Pitcher of the Month for the second time in the 2008 season. He went 5–0 with a 1.86 ERA in the month. On September 12, Lee won his 22nd game, making his record 22–2 for the season. This was the first time a pitcher had gone 20 wins over .500 since Bob Welch in 1990. Lee ended the year with a 22–3 record, a 2.54 ERA, and 170 strikeouts. He started 31 games, completed four, and had two shutouts. He pitched a total of 223⅓ innings. Lee was the American League champion for both wins and ERA in the 2008 season.
Lee's 2008 winning percentage of 88% was the twelfth best of all time, and the fourth best by a pitcher starting a minimum of 30 games. He was behind only Randy Johnson, Ron Guidry, and Lefty Grove. Lee's winning percentage is the second best in the Indians' history, behind Johnny Allen's 93.8% (15 wins, 1 loss, in 24 games) in 1937.
Lee earned several awards following the 2008 season. These included the AL Comeback Player of the Year Award, the Players Choice Award for AL Outstanding Pitcher of the Year, Sporting News Pitcher of the Year Award, Sporting News Comeback Player of the Year Award, and the Warren Spahn Award for best left-handed pitcher in Major League Baseball. On November 13, 2008, Lee was awarded the AL Cy Young Award. This made Lee the second straight Indian (and third overall) to win the award, following former teammate CC Sabathia, who won it in 2007.
On June 14, 2009, Lee pitched a no-hitter into the 8th inning in a game against St. Louis, striking out six and walking two. Lee allowed three hits in a complete-game shutout, improving his record to 4–6 and his ERA to 2.88.
On July 29 (just before the July 31 trading deadline), the Indians traded Lee (along with outfielder Ben Francisco) to the Philadelphia Phillies in exchange for Carlos Carrasco, Jason Donald, Lou Marson, and Jason Knapp.
In his first game with the Philadelphia Phillies, Lee pitched a complete game and took a 5–1 victory. He pitched a no-hitter into the sixth inning and batted two hits, including his first career double and a run scored. Through his first five games with the Phillies, Lee compiled a 5–0 record, 39 strikeouts in 40 innings pitched, and a 0.68 ERA.
Charlie Manuel named Lee as the starting pitcher for the first game of the World Series. Lee had posted a 2–0 record in the first two rounds of the playoffs. Lee would be pitching against his former Indians teammate CC Sabathia.
Lee pitched a complete game in Game 1 of the 2009 World Series, winning the game 6–1 against the New York Yankees. He allowed no earned runs during this outing. He was the first pitcher since Deacon Phillippe of the 1903 World Series to pitch a complete game in the World Series with ten or more strikeouts and no walks. However, Phillippe allowed two earned runs in his start, so Lee was the first to do so without allowing an earned run. In his next start (Game 5), Lee earned another victory, allowing five runs and three walks while striking out three in seven innings. The Phillies won the game 8–6. Despite winning both of his starts, the Phillies lost the series in six games.
On December 16, 2009, the Phillies traded Lee to the Seattle Mariners in exchange for J. C. Ramírez, Phillippe Aumont and Tyson Gillies.
Lee appealed a five-game suspension imposed on him for throwing over the head of Chris Snyder during a spring training game. Both the suspension and the accompanying fine were overturned. Lee made his Mariners debut against the Texas Rangers on April 30, where he earned a no-decision in a 2–0 loss to the Rangers. He earned his first win with the Mariners on May 11, in a 5–1 win against the Baltimore Orioles. Lee pitched three consecutive complete games in June. He was picked to the 2010 AL All-Star team but attended as a Ranger. With the Mariners, Lee went 8–3 with a 2.34 ERA, an 0.945 WHIP, and an 89/6 K/BB ratio. Despite this, the Mariners were struggling, and Lee was placed on the trade market.
On July 9, after a deal with the New York Yankees failed, Lee was traded to the Texas Rangers along with Mark Lowe in exchange for Justin Smoak and prospects Blake Beavan, Josh Lueke and Matt Lawson.
On August 6, against the Oakland Athletics, Lee earned his 100th career win going eight innings and allowing only one run with seven strikeouts.
Lee pitched Game 1 of the American League Division Series against Tampa Bay on October 6, 2010, the same day that Phillies' pitcher Roy Halladay pitched a no-hitter against the Reds in Game 1 of the National League Division Series. Lee pitched for seven innings. He gave up one run and struck out ten batters. There have been eight post-season pitching performances of at least ten strikeouts and no walks in baseball history, of which Lee has pitched the last four. Two of these were in the 2010 ALDS. In Game 5 of the series, Lee set the ALDS series strikeout record and tied the MLB record with 21 strikeouts. He pitched a complete game, striking out eleven batters and allowing one run, earning a win.
Lee continued his postseason mastery into the 2010 ALCS, when he allowed just two hits while striking out thirteen New York Yankees at Yankee Stadium in an 8–0 Texas victory in Game 3. Lee has also become the first person to pitch three 10-plus strikeout games in one post-season.
However, facing the San Francisco Giants' Tim Lincecum in the 2010 World Series, Lee gave up seven runs (six earned) and did not make it through five innings. The Rangers lost the game 11–7. Lee faced Lincecum once again in Game 5 of the World Series with the Giants having a 3–1 series advantage. He gave up a three-run home run to Édgar Rentería, which resulted in a 3–1 loss and the Giants winning the series.
On December 15, 2010, Lee signed a five-year and $120 million free-agent contract with the Phillies. The contract also included a vesting option for a sixth year. He joined a pitching rotation consisting of Roy Halladay, Roy Oswalt, Cole Hamels and Joe Blanton. Commentators called it one of the best rotations ever assembled. Halladay, Oswalt, Lee, and Hamels were dubbed the 'Phantastic Phour' by fans and the media. In returning to the Phillies (despite the higher salary offered to him by the Yankees), Lee mentioned the chance to win a World Series ring, the strength of the staff, the chance to throw to a pitcher instead of a designated hitter in the National League, the regular sellouts, and the passion of the fans. He said "I never wanted to leave in the first place".
In Lee's first game back with the Phillies on April 2, 2011, he pitched seven innings, allowing four hits and three runs, while striking out eleven and walking none. On May 6, in a game against the Atlanta Braves, he struck out a career-high 16 batters, allowing three runs in a 5–0 Philadelphia loss. On June 28, Lee pitched a third consecutive complete game shutout in a 5–0 victory over the Boston Red Sox. Lee was awarded the National League Pitcher of the Month award for June 2011. Lee went 5–0 and had a 0.21 ERA. Lee pitched three consecutive shutouts and 34 scoreless innings. By the end of the month, he had also personally outscored teams he opposed (he scored two runs in the month while only allowing one run).
On July 9, Lee hit his first major league home run against Tommy Hanson of the Atlanta Braves after a ten-pitch at-bat. Although the Phillies lost the game 4–1, it was the first home run by a Phillies pitcher since Chan Ho Park in April 2009. Lee then went on to hit his second major league home run on August 9 against Ted Lilly of the Los Angeles Dodgers. In the same game, Lee also recorded his 17th career double-digit strikeout game, resulting in a 2–1 Phillies win.
On September 26, 2011, Lee was the winning pitcher in a 4–2 game against the Atlanta Braves. He pitched six innings, gave up five hits and two runs, struck out six, and walked none. He finished up the regular season with a 17–8 record, but more significantly helped the Philadelphia Phillies to a 100-win season. It marks the third time in franchise history that the Phillies have won 100 or more games in a season. He also led the MLB in shutouts with six, the most shutouts for any major league starter since Tim Belcher, who pitched eight shutouts in 1989 for the Los Angeles Dodgers.
In the postseason, despite having the best regular season for a second year and again tipped to win the World Series, the Phillies were eliminated by the St. Louis Cardinals in the NLDS. Lee started Game 2 where he surrendered five runs, as the Cardinals made a comeback from a 4-0 deficit to win 5-4. The Cardinals eventually defeated Lee's former team, the Texas Rangers, in seven games to win the World Series.
Lee received poor run support throughout the entire 2012 season; particularly the first half. On April 18, in a game against the San Francisco Giants, Lee pitched ten shutout innings, but the Phillies eventually lost the game. On April 21, Lee was placed on the disabled list with an oblique strain. Despite pitching well throughout the spring, Lee didn't earn any wins until July 4 in a game against the New York Mets. He pitched eight innings, allowing two runs while striking out nine, resulting in a 9-2 road victory. Lee's streak of thirteen starts without any wins was the longest of any former Cy Young Award winner since Greg Maddux in 2008. On September 17, Lee recorded his 1,500th career strikeout in a game against the New York Mets. He finished the season 6-9, despite an ERA of 3.16 (which was below his career average) and the lowest walks per nine innings rate in the National League at 1.2.
Lee started the 2013 season as the Phillies' third starter. In his first start against the Braves, he pitched eight scoreless innings and earned a win with a 2-0 Phillies' victory. Lee was voted along with Domonic Brown to play in the 2013 MLB All-Star Game. He finished the season with a record of 14-8, an ERA of 2.87, 222 strikeouts, and a 1.3 BB/9 rate, which was, once again, amongst the best in the National League.
After Cole Hamels was sidelined with an injury, Lee was named the Phillies' opening day starter, starting against the Texas Rangers. He pitched five innings and earned a win, despite allowing eight runs. Lee was placed on the disabled list in May for a left elbow strain. He began to pitch again on June 10. He was removed from the disabled list on July 21, only to come out of a game early on July 31, once again experiencing elbow discomfort. Lee made 13 starts in 2014 going 4-5 with a 3.65 ERA.
On March 16, 2015, Lee was placed on the 60-day disabled list to start the 2015 season due to a left common flexor tendon tear, and missed the 2015 season. After the season, the Phillies declined his $27.5 million option, paying him a $12.5 million buyout and making him a free agent.
On February 23, 2016, Lee's agent Darek Braunecker told Fox Sports that a return to pitching for Lee would take "a perfect situation", indicating that the offer he wanted was not forthcoming.
Lee's repertoire included two fastballs (four-seam, two-seam) that reached 90-93 mph, an 85-88 mph cut fastball, an occasional slider, as well as a circle changeup and a curveball.
Lee usually appeared stoic and confident on the mound. It was considered one of his greatest attributes when pitching in pressure situations.
Lee and his wife, Kristen, have a son, Jaxon, and a daughter, Maci. Jaxon was diagnosed with leukemia at the age of four months, but after undergoing treatments, is currently in remission. The family now lives in Lee's home state, Arkansas.