The top 10 moments of Tony Gwynn's career

May 9th, 2022

SAN DIEGO -- Let's be honest, this list could span a lot more than 10 moments. Tony Gwynn's 20 years with the Padres made him a legend in San Diego, and when he retired in 2001, he capped a career as one of the greatest hitters in baseball history.

The totality of Gwynn's achievements is what stands out -- 3,141 hits, a .338 batting average, eight batting titles. But Gwynn also authored his share of indelible moments that helped to define an entire era of Padres baseball. Here's a subjective ranking of the 10 best moments in Gwynn's legendary career.

1) Hall induction
July 29, 2007
Not that there was ever much doubt that Gwynn was Cooperstown-bound. But it was the response from Padres fans, and baseball fans everywhere, that came to define his enshrinement. After receiving 97.6% of the vote, Gwynn was inducted in the summer of 2007, alongside Cal Ripken Jr., another legend. Gwynn and Ripken drew the largest crowd in the event's history -- a remarkable 82,000 people to celebrate two of the game's all-time greats.

2) 3,000th hit
Aug. 6, 1999
How fitting that Gwynn would record his 3,000th hit on the same day on the calendar that he recorded his 2,000th hit: his mother's birthday. In Montreal, Gwynn lofted a single to right field to reach the milestone. He was the 22nd player in National League/American League history to record 3,000 hits and the 11th to do so with one franchise.

3) Chasing .400
Among the greatest "what-ifs" in baseball history is what Gwynn might have done in his quest to finish with a .400 batting average. No qualifying hitter has finished hitting .400 or above since Ted Williams did so in 1941. Gwynn was hitting .394 -- the highest average since Williams -- in mid-August, when the sport shut down because of a strike. Perhaps it's statistically unlikely Gwynn would've improved his average by six percentage points in the final two months, but former Padres GM Randy Smith once noted, "I know Tony thought he would, and to me, if Tony thinks he’s going to do something, odds are he’s going to do it."

4) World Series home run at Yankee Stadium
Oct. 17, 1998
Gwynn's second appearance on the Fall Classic stage came 14 seasons after his first, an arduous wait that wore on Gwynn. When he finally returned to the World Series with a 98-win Padres team in 1998, he announced his presence with authority. The Padres and Yankees were tied at 2 in the fifth inning of Game 1 when Gwynn turned on a pitch from David Wells and sent it off the facade of the upper-deck, quieting a raucous Yankee Stadium. It was, Gwynn would later say, "the most exciting moment" of his 20-year career.

5) What a season!
Gwynn's 1987 season is one of the most criminally underrated seasons in baseball history. (Seriously, how on earth did he finish eighth in the NL MVP Award voting? Eighth?!) Gwynn won his second batting title that year, with a .370/.447/.511 slash line, a whopping 56 steals, a league-leading 218 hits, a Gold Glove Award and a bWAR mark of 8.6 -- tops in the National League. Gwynn is often remembered for his 1984, '94 and '98 seasons because of the way they ended. But his single greatest season was '87, marred only by the fact that the Padres finished with 97 losses. (For what it's worth, Gwynn won's 1987 MVP Award re-vote, handily.)

6) The Padres' first pennant
Gwynn was the superstar San Diego needed, arriving at just the right time. In the early '80s, the Padres had built a roster with a seamless blend of young talent and impactful veterans. That's when Gwynn burst onto the scene. He batted .351, reached his first All-Star Game and won his first Silver Slugger Award as the Padres rallied for the 1984 pennant -- the first in franchise history. In a decisive Game 5 of the NL Championship Series against the Cubs, it was Gwynn's two-out double that broke a 3-3 tie in the seventh inning.

7) The leap at the All-Star Game
July 12, 1994
Gwynn was the only National Leaguer to play all 10 innings of the 1994 Midsummer Classic in Pittsburgh. He led off the 10th with a single and raced home with the winning run on Moises Alou's game-winning double. Gwynn slid into the plate, then leapt, pumped his fist and leapt again. The image is iconic. The story behind it is quintessential Gwynn, who played the game with unadulterated joy and passion, no matter the stakes.

8) Batting title No. 8
It's certainly fitting that Major League Baseball chose to name the National League batting crown after Gwynn. His eight batting titles are the most in NL history -- and the last of those was truly remarkable. At 37, Gwynn was on a quest to become the first National Leaguer to win four straight. But he received a serious challenge from Larry Walker (and not to mention, a balky knee). With 10 days left in the season, Walker led Gwynn by five percentage points. But Gwynn finished by hitting .500 (14-for-28) in his final seven games, to end the season with a .372 batting average, six points ahead of Walker.

9) His final NLDS
Sadly, Gwynn didn't find himself on the big stage very often. But when he did, he made his presence felt. That includes the 1998 NL Division Series against the Astros. Gwynn hit an opposite-field double off Randy Johnson in a Game 1 pitchers' duel, eventually scoring the go-ahead run. Then, in a pivotal Game 3 at Qualcomm Stadium, Gwynn nailed Moises Alou with a perfect throw to third base, a key out during a tight game in the seventh inning. The Padres would win the game, 2-1, and the series in four games.

10) His final All-Star selection
July 12, 1999
Gwynn didn't play in the last of his 15 All-Star Games in 1999 because of knee problems, but it's undoubtedly one of his most memorable trips to the Midsummer Classic. Gwynn and Ted Williams had begun to foster a friendship toward the end of Gwynn's career, as he began threatening some of Williams' records. At Fenway Park, Gwynn escorted Williams to the mound for a memorable ceremonial first pitch -- two of the greatest hitters in baseball history, standing side by side. (Though not officially on the roster in 2001, Gwynn also was in uniform for the All-Star Game in Seattle, where he was honored with the Commissioner's Historic Achievement Award.)