Derek Jeter’s Road to Cooperstown

Derek Jeter
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Derek Jeter Early Career

Derek Jeter had mixed scouting reports coming out of High School. Legend has it that some scouts, while acknowledging his talents, believed the young shortstop from Kalamazoo, MI, to be too scrawny for Major League Baseball. The New York Yankees decided to take a chance and drafted Derek Jeter as the 6th overall pick of the 1992 draft. 

In 1994 Derek was awarded Minor League Player of the Year, following a fantastic season where he compiled a .344 AVG., with 50 SB according to a story . He would rise quickly through the minors until getting his big chance when he got called up to the show. His first appearance with the Yankees was May 29th, in a regular-season game against the Seattle Mariners. He played just 15 games the rest of that season but the Yanks had seen enough, Derek was their shortstop of the future. 

Rookie Success 

The following year was Derek’s first full season in the Majors. He batted .310 and added 10 home runs. His bat, combined with solid defensive play, helped the Yankees win the 1996 World Series against the Atlanta Braves. This was the Yankee’s first World Series Championship since 1978 and would prove to be the first of many for the Jeter/Yankee tandem. To cap off a memorable season, Derek was awarded the American League Rookie of the Year honors. This early success rocketed Jeter into the spotlight, eventually making him one of the most prominent faces in Major League Baseball.

The Dynasty 

Over the Jeter’s 20 year career, He and the Yankees would experience many milestones together, including 13 ALDS and seven ALCS appearances, and winning five World Series championships. Derek would also appear in 14 All-Star Games. In 2000 he became the first player in history to be named the Most Valuable Player for both the All-Star Game and the World Series, in the same year. Many consider the true dynasty era to be from 1996-2000. During this time the Yanks compiled four World Series championships, solidifying themselves as a dynasty. Possibly the most successful in sports history. Derek and the Yankees would win one more title in 2009 for the organization’s 27th. The chase for 28 continues with the new crop of Yankee stars, like Aaron Judge, with the much anticipated 2020 season. 

The Core Four

The dynasty was made possible by the “Core Four”, which included teammates Jorge Posada, Andy Pettitte, and Mariano Rivera. Although, Derek liked to use the phrase “Core Five” to include friend and teammate, Bernie Williams, according to his book ‘Jeter Unfiltered’ by Derek Jeter. Jeter states in his book “[Bernie] paved the way for the rest of us to have that opportunity. Without him, the Core Four might not have been allowed to happen.” Keeping this core group together played a large part in the team’s prolonged success.

These Men shared a special bond and friendship, and none stronger than that between Derek and best friend Jorge Posada. Alas, all good things must come to an end.  Bernie would retire in 2006 a few years prior to the 2009 Championship season. Derek would go on to watch Mo retire in 2010, Jorge in 2011 and then finally Andy in 2013. Derek was the last man standing. A very fitting end to the Core Four (Five).

The Captain

In 2003, George Steinbrenner named Derek Jeter the New York Yankees team Captain. Steinbrenner stated to the New York Times “He represents all that is good about a leader, I’m a great believer in history, and I look at all the other leaders down through Yankee history, and Jeter is right there with them.” per a YES article written By A.J. Herrmann. Derek was the first Captain since Don Mattingly. The title of Yankee Captain comes with tremendous honor and prestige, neither of which he took lightly. Derek lived up to the title of Captain every day, both on the field with his lead by example approach and off of it with his philanthropic work. He would remain Captain for the remainder of his career.

3K Hit Club

Derek Jeter would prove to be a hit machine exceeding the 200 hit mark eight times in his career according to Only six other players can claim that feat, including Ichiro Suzuki, Pete Rose, Ty Cobb, and Lou Gehrig. He accumulated 3,465 hits in his 20-year career. Number 3,000 came on a special five hit day in the Bronx, as seen in this MLB Youtube video, against the Tampa Bay Rays, in the form of a line-drive home run to left field.


A very uncharacteristic hit for Derek, who had only two prior home runs that season. He became the first ever to join the 3,000 hit club as a Yankee. Derek places sixth on the total hits list behind Rose, Cobb, Hank Aaron, Stan Musial, and Tris Speaker.


Derek gave baseball fans many special moments. Whether it was the “Mr. November” home run in Game 4 of the 2001 World Series, “The Dive” catch into the stands, the “The Flip play”, or his signature “Jump-Man” throw from the hole. Jeter was the epitome of poise, class, and clutch performance throughout his career. Especially when it counted the most, the playoffs. Never braggadocios, or boastful. He was always as gracious in defeat as he was in winning. He loved being a New York Yankee. It showed in his every interaction with fans and even the media. Derek defined a generation of baseball for millions. He was everything the Yankees and their fans could have ever wished for.

The Derek Jeter story will be adding on the final chapter in 2020. 161th Street outside of Yankee Stadium will reportedly be named after him, according to a NY Daily News article written by Sarah Valenzuela. In addition, the 2020 Hall of Fame class is set to be announced on Tuesday, January 21st, and I suspect Yankee fans will have one more reason to celebrate their beloved Captain. Derek, thank you for everything you have done for Yankee fans and the game of baseball. We tip our caps to you.