Tony Gwynn

Gwynn received scholarship offers to play college basketball, but none for college baseball. He also went unselected in the 1977 MLB draft, which Gwynn attributed to his limited playing time. He wanted to play both sports for Cal State Fullerton, which was okay by basketball coach Bobby Dye, but baseball coach Augie Garrido did not believe an athlete could handle both sports in college. San Diego State basketball coach Tim Vezie wanted Gwynn to commit to playing two years of basketball before playing baseball. Gwynn also had an offer from Texas Christian University (TCU). However, he was told that he would be their first black player in 30 years, which ruled them out from his consideration. He chose to attend SDSU, calling it "the best option I had".

By the following season in 1979, Gwynn still had not heard from Aztecs baseball coach Jim Dietz about joining the team after the basketball season. However, an opportunity arose after two outfielders riding bicycles were struck by an automobile and injured, and Dietz was in need of replacements. Freshman shortstop Bobby Meacham, who played against Gwynn in high school, convinced the coach to give Gwynn a chance. Dietz had never seen Gwynn play, but contacted him mostly because he trusted Meacham. Vezie by then had been fired, and his successor, Smokey Gaines, allowed Gwynn to play baseball. Were it not for the accident, Gwynn doubted he would have ever played baseball with SDSU. "Knowing what I now do about Coach Dietz ... [h]e's too loyal to his athletes to have allowed me to walk over after basketball season and join the team." said Gwynn.

In baseball, Gwynn was primarily a left fielder and designated hitter (DH) at San Diego State. Gwynn hit .301 in his first season, but said he "stunk defensively". In 1980, Gwynn hit .423 with six home runs and 29 runs batted in (RBI) and was named third-team All-American by Baseball News. The next season, he was a first-team All-American after batting .416 with 11 home runs and 62 RBI. He also was named a first-team all-WAC outfielder. In his three years, he had a career average of .398 and the team went 146–61–4.

Gwynn indirectly received exposure from scouts watching SDSU that were interested in Meacham, who would become a first-round pick in 1981. Gwynn had started the baseball season late in 1981 as the basketball team was still competing, and some scouts had already seen enough of Meacham and stopped following SDSU. Also on the Aztecs baseball team was Casey McKeon, son of Jack McKeon, who was the San Diego Padres general manager at the time. Given his son's involvement, McKeon often went to Aztecs games. He was initially interested in seeing Meacham, but became more impressed by Gwynn after seeing him at an exhibition game between the Aztecs and Padres; Gwynn had just re-joined the baseball team five days earlier.

Coming out of college, Gwynn was initially worried about the transition from using an aluminum bat to a wooden one, but his concerns were allayed once he found a bat comparable to the size he had used with the Aztecs. He led the Northwest League with a .331 batting average, and added 12 homers and 17 stolen bases in just 42 games for Walla Walla, San Diego's Class A minor league affiliate, earning him most valuable player (MVP) honors for the league in 1981. He finished the season in Class AA with Amarillo for 23 games while batting .462.

Gwynn participated at spring training with San Diego in 1982, and hit an impressive .375. However, the Padres were set in the outfield with veterans Gene Richards, Ruppert Jones, and Sixto Lezcano, and Gwynn began the season with Triple-A Hawaii. He was batting .328 in 93 games with the Islanders when he was promoted and debuted for the Padres on July 19, 1982. He started in center field against the Philadelphia Phillies in place of a slumping Jones. In his fourth at-bat, Gwynn got his first major league hit—a double—against reliever Sid Monge. Rose, who was the Phillies first baseman and later became the major-league all-time hit leader, told Gwynn, "Congratulations. Don't catch me in one night." Five weeks later against Pittsburgh, Gwynn injured his left wrist after diving for a ball and hitting the hard artificial turf at Three Rivers Stadium, and missed three weeks while on the disabled list (DL). He finished his rookie season batting .289 in 54 games, the only season in his career he hit below .300. His 15-game hitting streak was the longest on the team that season.

Gwynn's career paralleled that of Wade Boggs, who also debuted in the major leagues in 1982. Gwynn and Boggs were the premier contact hitters in an era dominated by home runs. They both won multiple batting titles—Gwynn's eight to Boggs's five—and each won four straight to join Cobb, Hornsby, and Carew as the only players to do so. Gwynn and Boggs each hit over .350 in four straight seasons, the only players to do so since 1931. They joined Brock and Carew as the only players whose careers ended after World War II who finished with 3,000 hits and fewer than 160 home runs. Gwynn, though, had a career slugging percentage of .459, higher than comparable contemporaries such as Boggs, Brock, Carew, and Rose. Among that group, he had more RBIs (1,138) than everyone but Rose.

Nicknamed "Captain Video", Gwynn used video to study his swing before it became common in baseball. When he began the practice in 1983, MLB teams were years away from using video for scouting. Hoffman said that Gwynn "revolutionized video in baseball". Gwynn prospered during the steroid era of baseball. While other players were transforming their physiques over a single offseason, his body grew pudgier and rounder. Though no longer the base stealer or defensive player he was early in his career, he continued to excel as a hitter. From 1995 through 2001, Gwynn hit a major league leading .350 while power hitters were recording the six highest single-season home run totals in MLB history.

In his first full season in 1984, San Diego won their first NL West title. Gwynn was elected to start in his first All-Star Game, and he won his first batting title with a .351 average along with 71 RBIs, and 33 stolen bases; he had only 23 strikeouts in 606 at-bats. He finished third in the balloting for the National League MVP behind Chicago Cubs winner Ryne Sandberg and runner-up Keith Hernandez of the New York Mets. He had 213 hits, breaking the Padres record of 194 set by Richards in 1980. Gwynn hit second in the Padres batting order behind Alan Wiggins, and benefited from the higher number of fastballs opposing pitchers threw in response to the speedy leadoff hitter (70 SB) being on base. Wiggins' speed also disrupted the defense and opened up holes that Gwynn was able to exploit for hits. He hit above .400 when Wiggins was on base ahead of him. "Anybody can hit a fastball", said Gwynn. The duo was one of the biggest reason behind San Diego's success. They could score fast with Wiggins getting on first, stealing second, and Gwynn singling him home. Gwynn batted .410 with runners in scoring position, and Manager Dick Williams said his records indicated that Gwynn had the best "RBI percentage" on the team.

In the playoffs, the Padres won the first NL pennant in its team history, defeating the Cubs in the National League Championship Series (NLCS) before losing the World Series to the Detroit Tigers. Gwynn batted .368 in the NLCS and his one-out single in the bottom of the ninth in Game 4 set up Steve Garvey's game-winning homer. Gwynn hit .263 (5-for-19) in the World Series, and flew out to Tigers left fielder Larry Herndon for the final out of the fall classic. During the offseason, Gwynn took less money to stay in San Diego by signing a six-year, $4.6 million contract with the Padres. Still, his new salary of more than $500,000 salary for 1985 represented a sizable raise over the $180,000 he would have received, or the $100,000 he had received in 1984.

Gwynn's physical appearance belied his athleticism. He stood 5 feet 11 inches (1.80 m), thick around the middle and thighs. Even at his athletic prime when he could really run, he weighed around 200 pounds (91 kg) and was considered pudgy. His roly-poly frame was a self-described "body by Betty Crocker", a reference to the food product brand. Towards the end of his breakout season in 1984, he conceded that his "extra weight hasn't helped me. My bat's slower than it has been all year." At the time, he attributed his weight gain to soft drinks: "It's killing me. It's always been a weakness. I've gotta cut down on the soda pop." Jim Murray of the Los Angeles Times opined in 1993 that Gwynn's "deceptive" looks and not "look[ing] the part" contributed to his regularly being overlooked in the voting for league MVP. Gwynn was sensitive about his weight. His knee injuries over his career prompted the Padres organization, media, and fans to question his weight, conditioning, and eating habits. However, he rejected the notion that his weight led to his injuries. Gwynn contended that his weight was only a topic when he was struggling, and not when he was performing. He also believed that the criticism stemmed mainly from his not fitting people's profile of what an athlete should look like. He said he had "a football player's body", with his father, grandfather and brothers also being big. Gwynn said his hitting style put a lot of torque on his knees. He started experiencing problems with his legs in 1986, when he suffered from shin splints. In his career, he had 13 operations, including eight involving his knees. Limited by injuries, he played over 135 games just once in his final 11 seasons. Gwynn used to run a great deal to keep in shape, but his last five years were mostly limited to working out in the gym. His actual weight is generally thought to have been under-reported during the latter part of his career, when it was officially listed between 215 and 220 pounds (98–100 kg).

Gwynn placed in the top 10 in voting for the National League MVP seven times in his career, including his only top-five finish in 1984, when he ended up third. In 2005, Sporting News ranked Gwynn No. 57 on the list of their 100 Greatest Baseball Players, and he was nominated as a finalist for the Major League Baseball All-Century Team. However, Gwynn's significance is muted by the non-traditional measurements in sabermetrics, which tends to favor power and the ability to get on base over batting average. As of 2014, his career 65.0 WAR ranked 34th among outfielders, and a few above him had not yet been voted into the Hall of Fame. While he had a first-rate on-base percentage of .388, he was one of only four players to hit .335 or more who did not have career .400 OBP. During his career, he finished in the top-10 in the NL in OBP 10 times. Gwynn's run production was another rap against him. He exceeded 90 RBIs in a season just once, when he had 119 in 1997, but he batted .349 in his career with runners in scoring position. "He was devastating with runners in scoring position. Impossible", former player Eric Davis said.

Wiggins entered drug rehab in 1985 and was traded later in the season to the Baltimore Orioles, resulting in Gwynn seeing fewer fastballs and more breaking balls. Gwynn said it took him a month to realize the change in opponents' strategy, and a while to adjust. His average was under .300 into June, when he got hot but then sprained his wrist on June 27 in a collision with Dodgers catcher Mike Scioscia. Still, Gwynn was named with seven other Padres to the 1985 All-Star Game. San Diego was leading the NL West at the time, but finished the season in third place. After Gwynn's wrist healed, he hit .339 after the start of August and finished the season with the fourth-highest average in the NL (.317). Without an adequate replacement for Wiggins batting leadoff, his RBIs fell to 46.

Gwynn played a career-high 160 games in 1986, when he led NL position players in Wins Above Replacement (WAR). He scored 100 runs for the first time, and tied for the NL lead (107). He set then-career highs for doubles (33), homers (14) and steals (37). On September 20 against the Houston Astros, he had four hits and became the fifth NL player that century with five stolen bases in a game. He finished third in hitting (.329) after leading for most of the season. He hit only .296 in September, and he regretted paying too much attention to Tim Raines and Steve Sax, who were previously trailing him. Gwynn was honored for his defense with his first Gold Glove after leading the league in total chances and putouts (337). His 19 outfield assists that year, which were one short of the league high, were highlighted by the three Mets he threw out in one game.

Despite his financial problems and bankruptcy in 1987, Gwynn remained unfazed on the field. In the Padres home opener, Marvell Wynne, Gwynn, and John Kruk hit back-to-back-to-back homers to start the game for San Diego, the first time an MLB team had led off a game with three consecutive home runs. In June, he had 44 hits in 93 at-bats for a .473 average, the best month in his career. He finished fifth among NL outfielders voting for the All-Star game, which Padres manager Larry Bowa called "a joke". However, Gwynn was unperturbed: "People put a premium on the home-run hitters. I know what I am. I’m a contact hitter and not a home-run hitter ... I’m not going to try to be something I’m not."

During the last three months of the 1987 season, a finger on Gwynn's left hand would lock when he gripped a bat. It would come open barely enough for the bat to slip out from his grip. He had surgery on the hand during Spring training the following season. Early in 1988, Gwynn was on the DL for 21 days after spraining his thumb after tripping rounding first base in Pittsburgh. He was hitting .246 as late as July 2, 1988, but won the championship with a .313 average. Gwynn batted .406 in July and .367 in the last 73 games of the season. He denied that injuries impacted his hitting, instead attributing his struggles to "mechanics". He struck out a career-high 40 times that season, while his .313 average was the lowest to win a title in NL history. In the 112 years before, only nine batting leaders hit below .330, the previous low being Larry Doyle's .320 in 1915. For the 25 years ending in 1988, batting leaders averaged .343. Gwynn hit 119 points higher with runners on base (.382) than with the bases empty (.263), the largest differential in the NL that season. He tied Pedro Guerrero for the highest average with runners in scoring position (.371). During the season, McKeon replaced Bowa as Padres manager, and moved Gwynn from right to center field. Gwynn also reached 1,000 career hits on April 22 with a single off Nolan Ryan of the Astros. On September 17, he passed Dave Winfield as the Padres career leader in hits with his 1,135th off Jim Acker of the Atlanta Braves.

In the 1989 season, he was hurting in September while he was in the race for another batting title. His right toe made it hard for him to put a shoe on, and his left Achilles tendon was sore and prevented him from pushing off properly when swinging. His batting average dropped, but he insisted on playing until his manager forced him to sit out for two games. The Padres were battling the San Francisco Giants for the division title in September, but they were eliminated from contention the game before hosting a season-ending three-game series with the Giants. Although the race for the division was over, Gwynn was still trailing San Francisco's Will Clark for the batting title, .333 to .332. Gwynn went 3-for-4 in the last two games, finishing at .336 to claim his third title. "I lost to the best", Clark said. Gwynn became the first NL player to win three consecutive batting titles since Musial in 1950–52. In December 1989, Gwynn fell to being the seventh-highest-paid Padre at $1 million a year, and he questioned the team's salary structure. He felt he deserved more money than players like Jack Clark, who signed a lucrative deal with the New York Yankees before being traded to San Diego. Gwynn's request for a contract renegotiation was denied.

Widely respected by his peers and known as one of the most dedicated players in baseball, Gwynn in 1990 was accused by some teammates of being selfish and caring more about his batting average than winning. First baseman Jack Clark, most notably, stated that Gwynn should be swinging with runners in scoring position instead of bunting and protecting his batting average. Clark did not approve of Gwynn bunting with runners on first and second with nobody out, believing he was trying to either bunt for a hit or get credit for a sacrifice if he failed. On the other hand, Gwynn felt he was advancing runners for the team's "game changers"—Clark and Joe Carter—which was consistent with McKeon's style. Gwynn said he resorted to bunting to advance the runners because he was not a good pull hitter. "No one bothers Tony Gwynn because he wins batting titles, but the Padres finish fourth or fifth every year", said Clark, who also stirred controversy on his prior teams. Teammates Mike Pagliarulo and Garry Templeton sided with Clark, who also said Gwynn was "50 pounds overweight", leading to his lower stolen base total.

Gwynn in 1991 passed Gene Richards as the Padres' all-time leader in steals and triples. He reached a season-high batting average of .373 in June, and late in the month was among the league leaders in RBIs. His left knee began causing him problems before the All-Star break, and he had been suffering from shin splints as well. He injured his left knee on August 5 at Houston while sliding into second base. He played through the injury, missing just one game over the next 3 ⁄2 weeks. He had fluid drained from his knee on August 31, and played just once in the week that followed while surgery was discussed. He attempted to finish out the season, but lasted just five more games. He underwent arthroscopic surgery to clean out the knee and smooth the articular cartilage, missing the final 21 games of the year. Gwynn was leading the league in hitting at .326 late in August, and had enough plate appearances already to qualify for the title, when many people—including his father and Padres announcer Jerry Coleman—advised him to take care of his knee and secure another batting title. However, Gwynn was still reeling from Clark's criticism over his conditioning and being selfish, and he wanted to continue playing. Gwynn finished the season ranked third in batting at .317, behind Terry Pendleton (.319) and Hal Morris (.318). After the All-Star Game, he hit just .243.

Gwynn entered the 1993 season anticipating that he would be better after his past two surgeries, and he had also incorporated Williams' advice into his swing. The Padres lost 101 games that year for the team's worst record during his career. They finished last in the division, behind even the Colorado Rockies, who were an expansion team in their inaugural season. San Diego that season had traded most of its star players—including Fred McGriff, Gary Sheffield, and Tony Fernández—in fire sales. Gwynn finished with a .358 average, the then-second best average of his career, but Colorado's Andrés Galarraga won the title at .370. He batted .587 on pulled balls, compared to his .315 in 1991 before Williams' pointers. Gwynn was affected early in the season by a sprained thumb, but he hit .400 (76-for-190) over the second half of the season. On June 10, he missed the opportunity to hit for the cycle when Manager Jim Riggleman replaced him in the seventh inning of a 14–2 rout against the Dodgers after he had hit for a home run, double, and triple in his three prior at-bats. Riggleman was not aware that he needed a single to complete the cycle. Still wary of Clark's earlier criticism that he was selfish, Gwynn did not contest his removal, which angered his manager when he found out after the game. On August 4 against the Giants, Gwynn had the only six-hit game of his career. He might have gone 7–for–7 if not for an excellent play at first base by Will Clark. Gwynn recorded his 2,000th hit with a single off Colorado lefthander Bruce Ruffin on August 6. His last game was September 5 before undergoing arthroscopic surgery to clear "loose bodies" from his knee. It was the fourth consecutive year his season ended early, and the third straight season it was due to left knee surgery.

Gwynn and Clark said they could continue to play together, but Clark signed with the Boston Red Sox as a free agent in the offseason. Gwynn felt appreciated after he was signed to a three-year contract extension for $12.25 million, including a $1 million signing bonus. McKeon praised Gwynn, saying, "He's one of the most unselfish players I've ever managed. In '89, when he was going for a batting title, he was giving himself up to move runners along." Dick Williams, who managed Gwynn from 1982 through 1985, said of Gwynn, "I don't think I've ever had a player who worked harder, cared more and was more deserving of his awards." Clark continued to criticize him, which Gwynn attributed to jealousy. Gwynn responded with his own criticism of Clark: "Let's talk about him walking 104 times, being a No. 4 hitter. Let's talk about his not flying on team flights. Let's talk about him getting booted out of games on a called strike three." In 1992, Gwynn sympathized with Clark, who filed for bankruptcy after bad loans by his agent. "I really appreciated the things Tony said about my situation", Clark said.

In 1992, Gwynn ended the season on the DL for the third straight year. On September 8 in a 16-inning game in San Francisco, he had the third five-hit game of his career and his first since 1987. He sprained the medial collateral ligament in his left knee in the same game, and played just four more innings the rest of the season. He required arthroscopic surgery on the knee. Gwynn met Hall of Famer Ted Williams for the first time during the 1992 All-Star Game, which was hosted at San Diego Jack Murphy Stadium (known later as Qualcomm Stadium). At the time, Gwynn considered himself to be an accomplished hitter, content to hit singles and doubles. Williams called Gwynn "a big guy", capable of hitting for more power. He chided Gwynn for using a "toothpick" for a bat. His encounter with Williams spurred him to think more about hitting, and he began to hit for more power. "I've never been a home run guy, never been a big RBI guy, but from that point to the end of my career, I was much better at it", said Gwynn.

Gwynn was the 11th player to collect all 3,000 hits with one team. George Brett of the Kansas City Royals and Robin Yount of the Milwaukee Brewers were the last to achieve the milestone for one team in 1992. He played his entire career for San Diego, a rarity for his generation in an era of free agency. "In this era it doesn't happen. It takes a little bit of loyalty and luck. It also takes the organization wanting a player to stay with the club", said Gwynn. He regularly took less money to keep his family rooted in San Diego, which prompted criticism from the MLBPA for his setting a lower market value for other star hitters. Gwynn earned $47 million as player, but never received more than $6.3 million in a season, nor signed a contract valued over $12.25 million. Only 17 MLB players have played at least 20 seasons with one club. He is widely considered the greatest Padres player ever. "There's simply no bigger figure in baseball that San Diego's ever had", said former teammate Trevor Hoffman. The San Diego Union-Tribune placed Gwynn No. 1 in their 2014 ranking of the city's most influential sports figures. He eschewed the added fame that might have come from playing elsewhere, opting instead to stay with the small-market team that had just seven winning seasons and three playoff appearances during his two decades with them. Gwynn transcended sports and became a civic icon. "It's rare, and becoming rarer, that one man is so identified with a franchise and a city as Tony is with San Diego and the Padres", said political columnist and baseball writer George Will. Grantland called him "quite simply, one of the most beloved figures in the history of the city of San Diego."

Gwynn was friendly and accessible to both the media and fans. Even on the occasions that he began an interview tight-lipped, he almost inevitably opened up and offered abundant material. He spoke with a twang in his high-pitched voice, often filled with loud, infectious, childlike laughter. Gwynn possessed a cheerful personality, being friendly towards others while being critical of himself. He considered himself "a good player ... but I knew my place. I was not a game-changer. I was not a dominant player". His demeanor was even-keeled; Rettenmund said, "You couldn't tell if [Gwynn had] gone 3-for-3 or 0-for-3." After the death of his father in 1993, Gwynn followed his father's advice and became more outspoken and more of a team leader.

In 1996, the Padres won the division with 91 wins and returned to the playoffs for the first time in 12 years. Gwynn called it the worst injury season of his career. His hurt heel in April was diagnosed as an inflamed bursa sac. He tried multiple shoes to alleviate the pain, and was on the DL for a month at midseason. He played the rest of the year in pain, and surgery after the season revealed a 40 percent tear (or fraying) at the top of his right Achilles' tendon. On September 28, Gwynn hit a patented single between third base and shortstop to score two runs and break a 2–2 tie in the eighth against the Dodgers, clinching a playoff berth for the Padres. He called it his most memorable regular-season hit until his 3,000th career hit. Gwynn's brother, Chris, also played for San Diego that season and hit the game-winner in the season finale in extra innings, completing a three-game sweep over Los Angeles to win the division. Chris had only hit .169 entering the game, and some fans were convinced that he was on the team only because of his brother. Earlier in the week, Gwynn had criticized fans for booing his brother. "Today, I'm just Chris Gwynn's anonymous brother," said Gwynn, who also won his seventh batting title that day. Although he was four plate appearances (PAs) short of the minimum to qualify for the title, MLB Rule 10.22(a)—which also came to be known as the Tony Gwynn rule—allowed hitless at-bats to be added to his record to qualify. Gwynn, who batted .353 in 498 PAs, would have dropped to .349 with the extra at-bats, still five points better than second-place Ellis Burks' .344. In the postseason, the Padres were swept by the St. Louis Cardinals in the opening round.

In April 1997, Gwynn signed a three-year contract extension for $12.6 million. Recovered from his Achilles problem the year before, he was able to plant his front foot to pull inside pitches. That season, Gwynn reached career highs with 17 home runs and 119 RBIs. He batted .372 for his eighth batting title, second only to Ty Cobb (12). He led the NL in hits for the seventh time, tying Rose's record. The 220 hits led the majors and was a new team record. Gwynn led the majors with a .459 average with runners in scoring position. In his 16th season, he became the oldest major leaguer at age 37 to reach 100 RBIs for the first time. His RBI total was the second-highest in club history. He also hit a Padres record of 49 doubles, ranking second in the league, and established a career-best of 324 total bases. On June 7, Gwynn hit his 100th career home run off of Donne Wall of Houston, becoming the third Padre to reach the mark. He was batting .402 on July 14, the latest in the season he had ever been at .400. However, his average tailed off as he suffered from kidney stones later in the month, and he also battled problems with his left knee that required postseason surgery.

In 1997, SDSU's baseball facility, Smith Stadium, was extensively renovated with $4 million from Padres owner John Moores. At Moores's request, the stadium was renamed Tony Gwynn Stadium.

Gwynn had three procedures to remove noncancerous growths from his parotid gland beginning in 1997. In 2010, he was diagnosed with cancer of a salivary gland and had lymph nodes and tumors from the gland removed. The operation left his face partially paralyzed on the right side, leaving him unable to smile. Later that year, he underwent eight weeks of chemotherapy and radiation treatments. He was declared cancer free afterwards, and also regained his ability to smile. Additional surgery was performed in 2012 to remove more cancerous growth and address nerve damage. Gwynn attributed the cancer to the dipping tobacco habit that he had since playing rookie ball in Walla Walla in 1981. Doctors, however, stated that studies had not linked parotid cancer with use of chewing tobacco.

In 1998, Gwynn batted .321 and helped the Padres win a franchise-record 98 games and their second pennant. He began the year with his first-ever opening-day home run, and continued his trend of hitting for more power with 16 homers for the season. The Padres reached the World Series in 1998 after defeating Houston and Atlanta in the playoffs. However, the Padres lost to the Yankees in a four-game sweep, despite Gwynn hitting .500 (8-for-16) in the series; the rest of the team batted only .203. Gwynn hit a home run off the second-deck facade in the opening game at Yankee Stadium against pitcher David Wells, which he calls his favorite hit and highlight of his career. "That's the biggest game in the world, a World Series game. And the fact that it was in New York in Yankee Stadium. I'll remember that forever", he said.

The Gwynn-Ripken induction weekend was notable for a number of attendance records, which were announced during the ceremony. 14,000 people visited the Hall of Fame Museum on July 28, a record number for a single-day. Baseball attendance for all games played on July 28 also set a single-day record. The induction ceremony also had the greatest collection of Hall of Famers present, 53 of the 61 living members. A record crowd estimated at 75,000 attended the induction ceremony, shattering the previous record of 25,000 in 1999. In 2002, Gwynn was also inducted by the San Diego Hall of Champions into the Breitbard Hall of Fame honoring San Diego's finest athletes both on and off the playing surface. A week before his induction, Gwynn appeared on a Wheaties box.

Gwynn was solid on defense, and won five Gold Gloves in a six-year span. He stole 318 bases in his career, with a high of 56 and a four-year stretch when he averaged 40. Only four players in MLB history had 300 steals and a career batting average of at least .338; Gwynn was the only one of the four to have played since 1928. He was also just the 10th player to retire with over 3,000 hits and 300 steals. Gwynn in 1999 was the first National League player to reach 3,000 hits since Lou Brock in August 1979. Seven American Leaguers reached the mark after Brock and before Gwynn; all but one played at least 400 games as a designated hitter. An NL player could not be a DH until 1997, when it was allowed for the few interleague games that were played in AL parks. Just six of Gwynn's first 3,000 hits came as a designated hitter. "If you want to do it in the National League, you have to play a position", he said. "It's been 20 years since anybody has been able to do it. That tells you how tough it is to do it in this league."

Gwynn, who turned 40 in 2000, had a left knee injury that required his knee to be drained seven times before he underwent season-ending surgery. He was limited to playing just 36 of the Padres' first 71 games, and he started only 26 games in right field. He batted .408 from May 19 to June 23 to raise his average from .196 and finish the season at .323. Gwynn had microfracture surgery performed on his knee, which involved tiny holes being created to promote cartilage growth.

The Padres bought out their $6 million option on Gwynn for 2001, paying him $2 million instead, and he became a free agent for the first time. After weeks of negotiation that were at times bitter, Gwynn re-signed with the Padres for 2001, agreeing to a one-year, $2 million contract with a chance to earn another $3.7 million in performance incentives. However, he was hampered that season by problems to his right leg, which had been his "good leg", and was limited to just 17 games on the field. In the first half of the season, he missed 64 games due to a right hamstring that resulted in two stints on the DL. After returning, he began having problems with his right knee. He was limited to pinch-hitting duties and started only one game after mid-July due to a torn meniscus in the right knee. Gwynn formally announced on June 28 that he would retire at the end of the season, and subsequently received an ovation at each stadium the Padres visited. He was honored as a non-playing squad member at the 2001 All-Star Game During the game, he and Cal Ripken, who had announced his retirement nine days before Gwynn, were presented the Commissioner's Historic Achievement Award by Commissioner Bud Selig. On October 6, 2001, at Qualcomm Stadium, Gwynn had a pinch RBI double off Gabe White of Colorado for the final hit of his career. He considered starting the next day in the final game of the season, but he was not confident he could handle a fly ball. In his final appearance, he pinch hit in the ninth inning, grounding out to shortstop. Although he was limited to only 112 plate appearances, Gwynn finished the season with a .324 average, his 19th consecutive season batting at least .300.

Following his playing career, Gwynn was the baseball head coach at SDSU for 12 seasons, compiling a 363–363 record including three Mountain West Conference championships and three NCAA Tournament appearances. During his last season playing for the Padres in 2001, he lobbied for the coaching position after Jim Dietz announced he would step down after the 2002 season. In September 2001, Gwynn signed a three-year contract with his alma mater to be an unpaid volunteer coach for 2002 with a base salary of $100,000 starting in 2003. In the five-year period 2007–2011, the baseball team was penalized with a reduction in scholarships for failing to meet the NCAA's Academic Progress Rate. However, Gwynn's teams improved their academic performance for the five years ending in 2012. The Aztecs finished .500 or better in five of Gwynn's final seven seasons, and they qualified for the NCAA Tournament three times in his final six seasons. As the Aztecs' coach, Gwynn oversaw the development of future major leaguers such as Justin Masterson and Stephen Strasburg, the No. 1 overall draft pick in 2009.

Gwynn was inducted into the Padres Hall of Fame in 2002, and the team retired his No. 19 in 2004. He was inducted into the California Hall of Fame in 2016.

Gwynn was married to Alicia Gwynn, and was the father of R&B singer Anisha Nicole and major league outfielder Tony Gwynn Jr., whose major league debut (with the Milwaukee Brewers) and first major league hit on July 19, 2006, came 24 years to the day of his father's first major league hit—each Gwynn hit a double. Gwynn's brother, Chris, was also a major league outfielder. Both Chris and Tony Jr. played with the Padres during their careers. Until Gwynn's death he split time between homes in Poway, California, and Fishers, Indiana.

In 2007, a 9½-foot (2.9 m), 1,200-pound (540 kg) bronze statue of Gwynn was unveiled in the park just beyond Petco Park's outfield in an area named Tony Gwynn Plaza. The address of Petco Park is 19 Tony Gwynn Drive.

On January 9, 2007, Gwynn was elected to the Baseball Hall of Fame, being selected on 532 out of 545 ballots (97.61%), the seventh highest percentage in Hall of Fame voting history. He was relieved that he did not exceed Tom Seaver's record of 98.8 percent. Gwynn considered his selection to be validation for the value of contact hitters, who are not as celebrated as power hitters. He was inducted alongside Cal Ripken Jr. on July 29, 2007. Ripken and Gwynn are two of the 46 players in the Hall of Fame who played their entire major league career for only one team. Both were elected almost unanimously in their first year of eligibility.

After his playing career ended, Gwynn's weight peaked at 330 pounds (150 kg), and he underwent adjustable gastric banding surgery in 2009 in an attempt to lose weight. He did not closely adhere to the diet, and his weight loss began to stall. In 2010, his weight problem led to a slipped disc in his back that affected a nerve down his leg. He needed a walker before he had the damaged disc removed to cure the pain while walking. Later, he experienced a loss of taste for food during radiation therapy for his cancer, and while being limited to a liquid diet, he lost 80 pounds (36 kg), all of which he regained after he resumed eating solid foods.

In May 2012, Gwynn joined a group led by movie producer Thomas Tull to bid on purchasing the Padres from Moores. Gwynn had no financial stake in the group, and Tull withdrew his bid in June.

Gwynn's bout with cancer caused him to miss time intermittently. He missed the start of the 2012 season after undergoing surgery, and missed games in 2013 while involved with a clinical trial. Days before his death in June 2014, he was given a one-year contract extension although he had been on a leave of absence since March while recovering from cancer treatment.

In 2014, the Mountain West Conference posthumously renamed its baseball Player of the Year Award to the Tony Gwynn Award. At the 2016 All-Star Game in San Diego, MLB announced that the annual winner of the NL batting title would be known henceforth as the "Tony Gwynn National League Batting Champion".

During another round of cancer treatments in April 2014, a mishap occurred in which Gwynn lost oxygen and was barely able to move. He was sent to rehabilitation to learn how to walk again. On June 16, 2014, Gwynn died at Pomerado Hospital in Poway due to complications from his cancer. He was 54 years old. The night before, on Father's Day, he had gone into cardiac arrest, and he was rushed from his home to the hospital.

A public memorial service was held for Gwynn at Petco Park on June 26, 2014. The service was attended by 23,229 fans, who heard tributes to Gwynn from baseball and civic leaders, and from Gwynn's family.

On May 9, 2017, a memorial statue in his honor was unveiled at Lake Poway.