Playing for Reitz Memorial High School’s baseball team, the Tigers, Mattingly led the school to a state record 59 straight victories through the 1978–79 season. The Tigers won the state championship in 1978 and finished as the runner-up in 1979. Mattingly was the L.V. Phillips Mental Attitude recipient in 1979. He was All-City, All-Southern Indiana Athletic Conference (SIAC), and All-State in 1978 and 1979. During the four years he played in high school, Mattingly batted .463, leading the Tigers to a 94–9–1 win–loss record. He still holds Reitz Memorial records for hits (152), doubles (29), triples (25), runs batted in (RBIs) (140), and runs scored (99). His 25 triples is also an Indiana state record. A multi-sport athlete, Mattingly was selected to the SIAC all-conference basketball team in 1978.

Following his high school career, Mattingly accepted a scholarship to play baseball for the Indiana State Sycamores. His father, Bill, informed Major League Baseball (MLB) teams that his son intended to honor that commitment and would not sign a professional contract. Mattingly lasted in the 1979 Major League Baseball draft until the 19th round, when he was selected by the New York Yankees. He was not interested in attending college, so he chose to sign with the Yankees, receiving a $23,000 signing bonus.

Mattingly began his professional career in Minor League Baseball with the Oneonta Yankees of the Class A-Short Season New York–Penn League in 1979. He hoped to bat .500 for Oneonta and was disappointed with his .349 batting average, which never went lower than .340. He batted a league-leading .358 in 1980 for the Greensboro Hornets of the Class A South Atlantic League in addition to recording a league-best 177 hits. He won the league MVP award and was named to the postseason All-Star team. With the Double-A Nashville Sounds in 1981, he hit .316 and led the Southern League with 35 doubles. He was selected to play in the Southern League All-Star Game and named to its postseason All-Star team.

Mattingly married Kim Sexton on September 8, 1979; they are now divorced. They have sons: Taylor, Preston, and Jordon. Taylor was drafted in the 42nd round (1,262nd overall) of the 2003 Major League Baseball draft by the New York Yankees, and played in 24 games for the Gulf Coast Yankees in the rookie league before an injury cut short his season. After sitting out all of 2004 and 2005, Taylor retired from baseball in 2005 after only 58 professional at bats. Of his eldest son, Don observed: “He loved the game, not the lifestyle.”

Despite Mattingly’s hitting ability, there were concerns about his lack of speed and power. Bob Schaefer, his manager at Greensboro, said that the organization considered moving him to second base, from which he would throw right-handed. Mattingly was batting .325 for the Columbus Clippers of the Triple-A International League when he made it to the majors late in the 1982 season. He was named to the league’s postseason All-Star team and finished third in the voting for the International League MVP Award.

Mattingly made his Major League debut on September 8, 1982, as a late inning defensive replacement against the Baltimore Orioles. He recorded his first at-bat on September 11 against the Milwaukee Brewers, popping out to third base in the seventh inning. His first career Major League hit occurred in the bottom of the 11th inning against the Boston Red Sox on October 1, a single to right field off of Steve Crawford. He only had 2 hits in 12 at-bats that season.

Mattingly made his major league debut in 1982, the year after the Yankees lost the World Series. The team did not reach the postseason in any of Mattingly’s first 13 years, although they arguably would have made the playoffs in 1994, when the players’ strike ended the season prematurely with the Yankees having the best record in the American League.

Mattingly became the Yankees’ full-time first baseman in 1984. With a batting average of .339, he was selected as a reserve for the 1984 All-Star Game. Heading into the final game of the season, Mattingly and teammate Dave Winfield were competing for the American League batting title, with Mattingly trailing Winfield by .002. On the final day of the season. Mattingly went 4-for-5, while Winfield batted 1-for-4. Mattingly won the batting title with a .343 average, while Winfield finished second with a .340 average. Mattingly also led the league with 207 hits. He hit a league-leading 44 doubles to go with 23 home runs. He was second in the league in slugging percentage (.537) and at bats per strikeout (18.3), fourth in total bases (324), fifth in RBIs (110), sixth in sacrifice flies (9), and tenth in on-base percentage (.381).

Mattingly was also recognized in 1985 for his defense, winning his first of nine Gold Glove Awards. He was considered such an asset defensively that Yankees management assigned him to play games at second base and third base early in his career, even though he was a left-handed thrower. Mattingly appeared as a left-handed throwing second baseman for one-third of one inning, during the resumption of the George Brett “Pine Tar Incident” game in 1983. He also played three games as a left-handed throwing third baseman during a five-game series against the Seattle Mariners in 1986.

Mattingly did just as well in 1986, leading the league with 238 hits, 53 doubles, and breaking the single-season franchise records set by Earle Combs (231 hits) and Lou Gehrig (52 doubles); both records had been set in 1927. He also recorded 388 total bases and a .573 slugging percentage. He batted .352 (second in the league), hit 31 home runs (sixth) and drove in 113 runs (third). However, he was beaten in the American League MVP voting by pitcher Roger Clemens, who also won the Cy Young Award that year. Mattingly also became the last left-handed player to field a ball at third base during a Major League game.

In 1987, Mattingly tied Dale Long’s major league record by hitting home runs in eight consecutive games, from 8–18 July (the All-Star game occurred in the middle of the streak; Mattingly, starting at first base, was 0 for 3). This record was later tied again by Ken Griffey, Jr., of Seattle in 1993. Mattingly also set a record by recording an extra base hit in ten consecutive games. Mattingly had a record 10 home runs during this streak (Long and Griffey had eight during their streaks). Also that season, Mattingly set a major league record by hitting six grand slams in a season (two during his July home run streak), a record matched by Travis Hafner during the 2006 season. Mattingly’s grand slams in 1987 were also the only grand slams of his career.

In June 1987, it was reported that Mattingly injured his back during some clubhouse horseplay with pitcher Bob Shirley though both denied this. Nevertheless, he finished with a .327 batting average, 30 home runs, and 115 RBIs, his fourth straight year with at least 110 RBIs. Between 1985 and 1987, Mattingly hit 96 home runs with just 114 strikeouts.

Mattingly hit 18 home runs and recorded 88 RBIs in 1988, but nonetheless was still in the top 10 in the league in batting average at a .311 clip. He rebounded in 1989 to 113 RBIs, but his average dipped to .303. Mattingly’s five runs scored on April 30, 1988, marked the 12th time it has been done by a Yankee.

Mattingly’s back problems flared up anew in 1990; after struggling with the bat, he had to go on the disabled list in July, only returning late in the season for an ineffective finish. His stat line—a .256 average, 5 home runs and 42 RBIs in almost 400 at-bats—came as a shock. Mattingly underwent extensive therapy in the offseason, but his hitting ability was never quite the same. Though he averaged .290 over his final five seasons, he became more of a slap hitter, hitting just 53 home runs over that timeframe. He did see a brief resurgence in power in 1993, hitting 17 home runs and driving in 86 runs in 134 games as the Yankees finished second in the division behind Toronto. In the strike-shortened 1994 season, he posted a .304 average, the first time since 1989 that he hit over .300. Mattingly’s defense remained stellar, but he was not always physically able to play.

Coincidentally, in 1991, before the episode aired but after it was produced, then-Yankees manager Stump Merrill told him that until he cut his hair, he would not play. This was in accord with Yankee owner George Steinbrenner’s policy requiring his players to maintain well-kept head and facial hair. Mattingly was sporting a longish or mullet-like hair style, and when he refused to cut it, he was benched.

Mattingly finished his career with 2,153 hits, 222 home runs, 1,007 runs scored, 1,099 RBI, and a .307 lifetime average. He is commonly cited as the best Yankee player to have never played in a World Series. His career had bad timing, as the Yankees lost the World Series the year before he broke into the big leagues and they ended up winning the World Series in the first year of Mattingly’s retirement, not to mention the Yankees had the best record in the American League in 1994 before the strike. This World Series drought (1982–1995) was the longest in Yankees history since the start of the Babe Ruth era and it was worsened by the player’s strike in 1994, which ended a promising chance for a World Series title.

Mattingly has been honored by two minor league Halls of Fame. He was inducted in the South Atlantic League Hall of Fame in 1994 and the New York–Penn League Hall of Fame in 2015.

In 1995, Mattingly finally reached the playoffs when the Yankees won the AL wild card on the next-to-last day of the season. In the only postseason series of his career, facing the Seattle Mariners, Mattingly batted .417 with six RBIs and a memorable go-ahead home run in Game Two, his final game at Yankee Stadium. In the final game of the series (and of his career), Mattingly again broke a tie with a two-run double. The New York bullpen faltered and Seattle won in the 11th inning of the decisive Game Five.

The Yankees acquired Tino Martinez to succeed Mattingly after the 1995 season. Unsigned for the 1996 season, Mattingly decided to sit out for the year, and rebuffed an inquiry by the Baltimore Orioles, who tried to sign him at midseason. Mattingly officially announced his retirement in January 1997.

The Yankees retired Mattingly’s number 23 and dedicated his plaque for Monument Park at Yankee Stadium on August 31, 1997. The plaque calls him “A humble man of grace and dignity, a captain who led by example, proud of the pinstripe tradition and dedicated to the pursuit of excellence, a Yankee forever.” Additionally, his uniform number with the Double-A Nashville Sounds (18) was retired by the team in a ceremony at Herschel Greer Stadium attended by Mattingly on August 12, 1999.

In 2001, Mattingly was inducted into the Indiana Baseball Hall of Fame; his plaque displays his phenomenal high school and professional career. In 1987, he was named the American Legion Graduate of the Year, for his success in the Major Leagues following his American Legion baseball career.

After retiring as a player, Mattingly spent seven seasons as a special instructor during Yankees’ spring training in Tampa, Florida from 1997 through 2003. Following the 2003 season, the Yankees named Mattingly the hitting coach. He spent three seasons in that role, receiving much praise from the Yankees organization and his players. Under Mattingly, the Yankees set an all-time franchise record with 242 home runs in 2004. After the 2006 season, Mattingly shifted to bench coach, replacing Lee Mazzilli.

In 2005, Mattingly launched Mattingly Sports, a baseball and softball equipment company, based primarily around the patented V-Grip baseball and softball bats.

After the 2007 season, Mattingly was a finalist for the Yankees’ manager position, after Joe Torre declined a one-year contract extension, along with Joe Girardi and Tony Peña. The Yankees offered the managerial position to Girardi, who accepted.

After not being offered the position of manager for the Yankees, Mattingly joined Torre with the Los Angeles Dodgers as the team’s hitting coach. On January 22, 2008, Mattingly was replaced as hitting coach, citing family reasons, instead serving as major league special assignment coach for the Dodgers in 2008. Mattingly succeeded Mike Easler as Dodgers’ hitting coach that July. The Dodgers were the National League Runner-up in 2008 and 2009 (losing to the Philadelphia Phillies in both National League championship series), largely behind the bat of mid-season acquisition Manny Ramirez.

In the 2009–10 offseason, Mattingly was a finalist for the managerial position with the Cleveland Indians, for which Manny Acta was eventually hired. When Torre decided to retire at the end of the 2010 season, Mattingly was announced as his replacement. To acquire some managerial experience, Mattingly managed the Phoenix Desert Dogs of the Arizona Fall League in 2010.

Preston was chosen in the supplemental round (31st overall) of the 2006 Major League Baseball draft by the Los Angeles Dodgers and was rated as a B- prospect in John Sickels’ 2007 Baseball Prospect Book. Sickels noted, “Position a question but has promising tools and bloodlines.” Preston was traded to the Cleveland Indians on September 26, 2010, just nine days after his father was announced as the manager of the Dodgers for the 2011 season. He was subsequently released by the Indians at the end of spring training, and re-signed with the Dodgers. On January 11, 2012, the Yankees signed Preston to a minor league contract but they released him again on March 27. Preston then attended Lamar University in Beaumont, Texas. He was from 2014-2015 a starting guard for the Lamar Cardinals basketball team, an NCAA Division I program in the Southland Conference.

Mattingly remarried on December 10, 2010, in his hometown of Evansville, Indiana. The wedding, as well as his managing the Phoenix Desert Dogs of the Arizona Fall League, prevented him from attending the Fall 2010 Winter Meetings.

Mattingly made his managerial debut on March 31, 2011 by defeating in-state rival and defending champion San Francisco Giants 2–1 at Dodger Stadium. Despite the background of a bitter divorce battle between Dodgers’ owner Frank McCourt and his wife that put the fiscal health of the Dodgers into jeopardy, Mattingly managed to take the Dodgers to a winning record that season due to his mentorship of many young players such as MVP candidate Matt Kemp and Cy Young Award winner Clayton Kershaw:

In 2013 Mattingly and the Dodgers got off to a rough start due to various injuries and were in last place in May, leading to much media speculation that he would soon be fired. However, once players got healthy the team went on a tear and managed to win the NL West and beat the Atlanta Braves in the NLDS in four games. They then lost to the St. Louis Cardinals in the NLCS in six games. After the season, Mattingly called out Dodger management for its perceived lack of support of him during the season and said that he wanted a multi-year contract in place in order to return in 2014. Mattingly finished second in the voting for National League Manager of the Year.

On January 7, 2014, Mattingly and the Dodgers agreed on a three-year contract extension for him to remain as manager of the Dodgers. On September 29, 2015, Mattingly became the first manager in the history of the Dodgers franchise, in both Brooklyn and Los Angeles, to lead the team to the playoffs in three consecutive seasons. The Dodgers lost in five games to the New York Mets in the National League Divisional Series.

On October 22, 2015 the Los Angeles Dodgers and Mattingly mutually agreed to part ways, and he stepped down from his position in Los Angeles with one year left on his contract. He had a 446–363 record with the Dodgers, with a winning percentage of .551 which was second best in Los Angeles Dodgers history. He finished with a post–season record of eight wins and 11 losses and was the first manager in franchise history to guide the team to three straight post-season appearances.

Mattingly was on the Hall of Fame ballot from 2001 to 2015, never getting enough votes for induction. In his first year, he received 145 votes (28.2%), but this steadily declined; by 2009, only 12% of voters still put him on their ballots. In 2015, Mattingly’s eligibility expired after fifteen attempts. He had been grandfathered onto the ballot after the committee restricted eligibility to ten years.