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Derek Jeter: A career retrospective

Derek Jeter’s No. 2 was by the Yankees to honor the man who helped lead the franchise to five World Series victories during his 20-year career. We look back on some of the future Hall of Famer’s greatest moments in baseball.


1 of 25

1992: Jeter drafted sixth overall

1992: jeter drafted sixth overall

Focus on Sport / Getty Images

Jeter was the sixth pick in the first round by the Yankees in 1992 and the only high school player taken in the first eight picks. He was drafted out of Central High School in Kalamazoo, Michigan.


2 of 25

1995: Jeter makes his MLB debut

1995: jeter makes his mlb debut

Rich Pilling / Major League Baseball

Derek Jeter’s MLB debut didn’t go particularly well, but it’s surely a day he will always remember. His first game occurred on May 29, 1995.


3 of 25

1995: Jeter’s first hit

1995: jeter's first hit

Rich Pilling / Major League Baseball

Jeter got his first hit in his second game, notching a single on a grounder to the left side off Mariners pitcher Tim Belcher.


4 of 25

1996: Jeter’s first home run

1996: jeter's first home run

David Liam Kyle / Sports Illustrated

Jeter started the 1996 season well, hitting a home run on opening day in the Yankees’ 7-1 win over Cleveland. He would go on to win AL Rookie of the Year.


5 of 25

1996: Jeter wins his first World Series

1996: jeter wins his first world series

Rich Pilling / Major League Baseball

New York defeated Atlanta in a six-game series, giving Jeter his first World Series win. The rookie went 5-for-20 with five runs scored during the series.


6 of 25

1996: Jeter wins AL Rookie of the Year

1996: jeter wins al rookie of the year

Focus on Sport / Getty Images

The much-hyped shortstop hit .314-10-78 with 14 stolen bases in 157 regular-season games during his rookie season. He also won his first of five World Series with the Yanks.


7 of 25

1996: The Jeffrey Maier catch

1996: the jeffrey maier catch

Al Tielemans / Sports Illustrated

Few sports fans are as infamous as a 12-year-old Jeffrey Maier, who reached over the Yankee Stadium wall in right field to turn a likely Jeter fly out into a home run in Game 1 of the 1996 ALCS vs. Baltimore.


8 of 25

1998: Jeter’s patented jump throw

1998: jeter's patented jump throw

Al Bello / Getty Images

Jeter’s defense is synonymous with his iconic jump throw. He let the world witness it in the 1998 playoffs when he robbed Indians third baseman Travis Fryman of a base hit.


9 of 25

1998: Jeter wins his second World Series

1998: jeter wins his second world series

Al Bello / Getty Images

The Yankees completed a sweep of the Padres in 1998, as Jeter earned his second World Series ring. He went 6-for-17 during the series.


10 of 25

1999: Jeter helps Yankees win back-to-back World Series

1999: jeter helps yankees win back-to-back world series

Jamie Squire / Getty Images

The Yankees completed their second consecutive World Series sweep in 1999, beating the Braves. Jeter went 6-for-17 during the series.


11 of 25

2000: Jeter wins All-Star MVP

2000: jeter wins all-star mvp

Rich Pilling / Major League Baseball

The Captain won the 2000 All-Star Game MVP, going 3-for-3. He was only the second Yankees player in history to win the honor.


12 of 25

2000: Jeter wins World Series MVP

2000: jeter wins world series mvp

Ezra Shaw / Getty Images

Jeter was on fire in the 2000 World Series, going 9-for-22 with two home runs in the Subway Series against the Mets.


13 of 25

2001: Jeter signs a huge deal

2001: jeter signs a huge deal

The Sporting News

Jeter solidified his status as a longtime Yankee when he signed a 10-year, $189 million contract before the 2001 season. He became the second highest paid player in baseball, trailing only Alex Rodriguez.


2001: the flip

New York Daily News Archive

One of the most well-remembered defensive players in history was sparked by Jeter in Game 3 of the 2001 ALDS vs. Oakland. Jeter came out of nowhere to flip a bouncing outfield throw home to catcher Jorge Posada, who was able to tag Jeremy Giambi and retain the 1-0 lead for the Yanks.


15 of 25

2001: Jeter’s walk-off homer in November

2001: jeter's walk-off homer in november

Al Bello / Getty Images

Jeter hit a walk-off home run in Game 4 of the World Series vs. Arizona. The Diamondbacks came back to win the series in seven games, however.


16 of 25

2003: Jeter is named team captain

2003: jeter is named team captain

Al Bello / Getty Images

Honored by manager Joe Torre, Jeter was named the team captain in 2003. He served in that role until the end of his career.


2004: the dive

Ezra Shaw / Getty Images

Known affectionately by Yankees fans as “The Dive,” Jeter risked life and limb to dive into the stands behind third base for an incredible catch on July 1, 2004. While Jeter did suffer facial scrapes, he was able to record the out against the Red Sox during the top of the 12th inning.


18 of 25

2008: All-Star Game at Old Yankee Stadium

2008: all-star game at old yankee stadium

J.P. Verni / Major League Baseball

Jeter was front and center when Old Yankee Stadium hosted the All-Star Game in its final season of 2008. He received a standing ovation when he left the game in the sixth inning.


19 of 25

2008: Jeter closes down old Yankee Stadium

2008: jeter closes down old yankee stadium

Jim McIsaac / Getty Images

The Captain did the honors with a final speech on Sept. 21, 2008, the final game at Yankee Stadium. The Yankees would move to new Yankee Stadium in 2009.


20 of 25

2009: Jeter becomes the Yankees’ all-time hits leader

2009: jeter becomes the yankees' all-time hits leader

Icon Sports Wire

Jeter surpassed Lou Gehrig’s 2,721 career hits with the Yankees to become the all-time hits king in pinstripes on Sept. 11, 2009.


21 of 25

2009: Jeter wins fifth World Series title

2009: jeter wins fifth world series title

Mike Coppola / FilmMagic

The Yankees beat the Phillies in six games to win the 2009 World Series, and Jeter had a tremendous series. He went 11-for-27, though outfielder Hideki Matsui won the series MVP.


22 of 25

2011: Jeter gets his 3,000th hit

2011: jeter gets his 3,000th hit

Nick Laham / Getty Images

Jeter reached 3,000 hits in style on July 9, 2011. He hit a home run off of Tampa Bay ace David Price to accomplish the feat.


23 of 25

2013: Jeter and Pettitte honor Rivera

2013: jeter and pettitte honor rivera

Mike Stobe / Getty Images

Future Hall of Fame reliever Mariano Rivera left the mound for the final time in 2013, getting pulled by longtime Yankees Derek Jeter and Andy Pettitte. While the moment centered around Rivera, it’s a legendary moment for the entire trio.


24 of 25

2014: All-Star Game goodbye

2014: all-star game goodbye

Elsa / Getty Images

Showing the respect fans around baseball had for Jeter, he received a standing ovation and curtain call after being removed in the fourth inning of the 2014 All-Star Game.


25 of 25

2014: Jeter ends career in clutch fashion

2014: jeter ends career in clutch fashion

Al Bello / Getty Images

Jeter ended his career the only way he knew how, with a game-winning hit in his last at-bat at Yankee Stadium. He was able to break a 5-5 tie in the 12th inning.

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