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Derek Jeter's career as a Yankee now spans (Credit: Newsday / Paul Bereswill)

Derek Jeter's career as a Yankee now spans almost two decades and is filled with memorable moments.

Derek Jeter's defining moments

From a high school shortstop whose life-long dream came true when he was drafted by the New York Yankees to a 13-time All-Star and five-time World Series champion revered as captain to the winningest team in baseball, Derek Jeter's career is one for the ages. It hasn't all been a fairy tale, though. Here's a look at his best and worst moments in pinstripes.

June 1, 1992 | The call

Jeter was a baseball star at Kalamazoo Central
(Credit: Kalamazoo Gazette/Landov)

Jeter was a baseball star at Kalamazoo Central High School when the Yankees called his parents' Michigan home to arrange a meeting. By June 27, 1992, a day after his 18th birthday, Jeter had signed on with his favorite team for $800,000 as a first-round draft pick, sixth overall.

May 29, 1995 | The big leagues

When Yankees shortstop Tony Fernandez was put on
(Credit: Newsday/Paul J. Bereswill)

When Yankees shortstop Tony Fernandez was put on the disabled list, Jeter was called up from the minor leagues. In his second game, he got two hits and scored his first major-league run. Baseball America rated Jeter the sixth-best prospect in baseball, and manager Joe Torre insisted he would be the team's starting shortstop going into the 1996 season.

1996 | A dynasty is born

What a year 1996 was for Jeter. It
(Credit: Getty Images/Henny Ray Abrams)

What a year 1996 was for Jeter. It started with his first major-league home run on Opening Day and ended with his first World Series championship against the Atlanta Braves, the first for the Yankees since 1978. Jeter batted .361 in the playoffs and was named American League Rookie of the Year.

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1998 | Officially an All-Star

Jeter helped the Yankees bounce back from a
(Credit: Newsday/Audrey C. Tiernan)

Jeter helped the Yankees bounce back from a disappointing 1997 season as the team won a franchise-record 114 games. He made his first appearance in the All-Star Game and led the American League in runs scored with 127. He batted .353 in the World Series, and the Yanks swept the San Diego Padres in four games.

1999 | On top of the world

Jeter set career highs in batting average, home
(Credit: Leslie Mazoch)

Jeter set career highs in batting average, home runs, RBIs, on-base percentage, slugging percentage, triples and walks, and he had a 17-game hitting streak in the postseason that dated back to 1998. He hit .375 in the playoffs as the Yankees went 11-1 against the Rangers, Red Sox and Braves on the road to their third World Series title in four years.

2000 | MVP times two

In 2000, Jeter became the first to be
(Credit: Getty Images/John Mabanglo)

In 2000, Jeter became the first to be named Most Valuable Player in both the All-Star Game and the World Series in one season. The only thing sweeter than that for the superstar shortstop? Beating the Mets in the Subway Series, with a .409 batting average and two homers.

2001 | Mr. November

The fall of 2001 was a trying time
(Credit: Newsday/John Keating)

The fall of 2001 was a trying time for New Yorkers and the entire nation, and the Yankees' championship race gave the city something to cheer for again. The Arizona Diamondbacks won the World Series in the end, but the energy at Yankee Stadium was unforgettable. Known for thriving under pressure, Jeter hit a walk-off home run in the bottom of the 10th inning of Game 4, giving the Yankees a win in the first MLB game ever completed in November and earning himself the nickname "Mr. November."

June 3, 2003 | The captain

After getting 191 hits for the second straight
(Credit: Newsday/Jiro Ose)

After getting 191 hits for the second straight season in 2002 and continuing to distinguish himself as a leader on and off the field, the Yankees named Jeter their captain. He was just the 11th captain in the history of the Yankees, and the first since Don Mattingly retired eight years before. He suffered a shoulder injury on Opening Day 2003 and missed the first six weeks of the season, but he didn't waste any time upon his return, nabbing 29 hits in his first 23 games. After a come-from-behind win against their rival Boston Red Sox, the Yankees advanced to the World Series but lost to the Florida Marlins that year.

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2004-2006 | The "Golden" era

Jeter's prowess in the infield won him the
(Credit: Newsday/David L. Pokress)

Jeter's prowess in the infield won him the Gold Glove Award for three straight seasons from 2004 to 2006, which he rounded out with a Silver Slugger Award in 2006 for being the best offensive shortstop in the league. The Yankees did not capture any World Series championships in that time, but they did keep up a nine-year streak of division titles.

2008 | The year the lights went out

The final season ever played in the old
(Credit: Newsday/David L. Pokress)

The final season ever played in the old Yankee Stadium, "The House that Ruth Built," was perfect in some ways and a huge disappointment in others. Jeter moved past Lou Gehrig and will forever hold the record for most hits at the old stadium. The final game played there on Sept. 21, 2008, ended with a 7-3 win for Andy Pettitte, with the final three outs thrown by Mariano Rivera before the captain faced the crowd for a heartfelt farewell address. However, just two days later, the Yankees were officially eliminated from playoff contention and would be sitting out of the postseason for the first time since 1993.

2009 | They're baaack

Though Jeter didn't get his picture-perfect ending in
(Credit: Getty Images)

Though Jeter didn't get his picture-perfect ending in the old Yankee Stadium, the new stadium's initiation couldn't have been better. Jeter passed Gehrig to become the Yankees' all-time hits leader on Sept. 11, batted .407 in the World Series, and, most importantly, the Core Four of Jeter, Rivera, Pettitte and Jorge Posada captured their fifth World Series rings after defeating the Philadelphia Phillies in six games.

July 9, 2011 | DJ3K

Fans went wild as Jeter chased 3,000 hits
(Credit: Jim McIsaac)

Fans went wild as Jeter chased 3,000 hits in the summer of 2011, and the captain reached the milestone with his signature flair. Jeter went into the game against the Tampa Bay Rays two hits short, started with a lead-off single, and in his next at-bat crushed a home run off of David Price, making him only the second player in history to hit 3,000 in such grand fashion. He had three more hits after that, going 5-for-5 and batting in the go-ahead RBI in the Yankees' win.

2012-2013 | Struggle to stay healthy

After a strong 2012 regular season that kicked
(Credit: Getty Images)

After a strong 2012 regular season that kicked off with a hot streak in April and finished with Jeter having the most hits in baseball, the shortstop fractured his ankle during Game 1 of the American League Championship Series as horrified Yankees fans looked on. He spent the offseason rehabilitating, and although he still showed glimpses of his old self -- the first pitch he faced in 2013 was a home run -- Jeter would face multiple physical setbacks during that "nightmare" season and was only able to play in 17 games.

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2014 | The grand finale

Before reporting for spring training, Jeter made a
(Credit: Getty Images/Al Bello)

Before reporting for spring training, Jeter made a pivotal announcement. "I know it in my heart. The 2014 season will be my last year playing professional baseball," he wrote in a letter posted on Facebook. "But before that, I want to soak in every moment of every day this year, so I can remember it for the rest of my life. And most importantly, I want to help the Yankees reach our goal of winning another championship."

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