For any true baseball fan, yesterday’s public announcement that New York Yankees shortstop and team captain Derek Jeter was retiring as a professional player is truly the end of an era.

For myself specifically, it is yet another reminder that I am getting older too. And it also marks a fantasy baseball loss to me, one that I will comment on more in a moment. But first let’s take a look at Jeter’s real world playing career, and a glance into his highly publicized personal life.

Derek Jeter broke into the big leagues on May 29th, 1995. To put this into a personal context, I was just 33 years old, and it was more than four months before my wife and I were married – we just celebrated our 18th wedding anniversary this past fall. He was only 19 years old then. A day later he recorded his first two career hits for the Yankees. The team was the most storied franchise in baseball history, but it had fallen on hard times.

It may be hard for some to remember, but at the time of Jeter’s arrival in a Yankees uniform the franchise had not won an AL East title or American League pennant in 15 years, and at that point it was 18 years since their last World Series crown. From 1987-92, the Yanks finished no higher than 4th place in their division, the last four of those with losing records.

TheYanks began to emerge from those dark days with a 2nd place finish in the 1993 season, and in 1994 were solid contenders when the devastating lockout hit all of Major League Baseball, ending the season prematurely. Having re-emerged as a contender, the usually big spending Yankees were uncharacteristically infused for the 1995 season with talented, homegrown talent in the form of what has become famously known as the “Core Four” players.

That core was made up of Jeter, catcher Jorge Posada, starting pitcher Andy Pettitte, and relief pitcher Mariano Rivera. The four had all played together throughout their minor league careers, and all broke into the big leagues together in that 1995 season. Together they would lift the Yankees franchise back to the top of the game, starring together on baseball’s biggest stage for the next 17 seasons.

In that very first season together, Jeter helped lead the Yankees back to the playoffs, with a 2nd place finish in the AL East and a Wildcard playoff berth. In those playoffs, they would lose in dramatic fashion to the Seattle Mariners, a team featuring baseball’s top two young superstars in Ken Griffey Jr. and Alex Rodriguez, the latter of whom would ultimately become a major part of Jeter’s career.

The following 1996 season was Jeter’s first full MLB season. Expected to be a strong fielding shortstop who tossed in a few hits now and then, he quickly showed that he was so much more. He hit .314, knocked in 78 runs, scored 104 runs, and was named the American League Rookie of the Year. Not only that, but he led the Yankees to the AL East title, AL pennant, and their first World Series crown in 28 years.

After finishing in 2nd place in 1997 and losing a heart-breaking 3-2 playoff series to the Cleveland Indians, Jeter and the Yankees would go on an unprecedented modern day roll. They would win 9 straight AL East titles from 1998-2006, and 3 straight World Series from 1998-2000. They reached the Series again following the attacks of 9/11 in 2001, losing one of the greatest World Series in history to the Arizona Diamondbacks in 7 games.

Thanks to a game-winning walkoff homerun in Game #4 of that 2001 World Series, Jeter earned one of his two nicknames as “Mr. November“, based on the fact that the game, which began on Halloween night, had moved past midnight, and thus he hit the dramatic homerun in the first-ever MLB game being formally played in the month of November. It was also an homage to the “Mr. October” nickname of former Yankees legend Reggie Jackson.

During the playoffs earlier in that 2001 post-season, Jeter perfectly highlighted his other “Captain Clutch” nickname, bestowed upon him because of the numerous clutch hits and defensive plays which he had a penchant for delivering. Jeter helped beat the upstart Oakland A’s with a heads-up defensive masterpiece that has become known in baseball lore simply as “The Flip“, a play that you have to see and would need a genuine understanding of the game to fully appreciate.

In 2003, the Yankees returned to the World Series as favorites, but were stunned by a young, talented Florida Marlins team. But they continued to win throughout the first decade of the new century as Jeter was joined the following season of 2004 by Rodriguez, one of baseball’s top shortstops himself who moved over to 3rd base in deference to the presence of the Yankee captain.

Jeter and ARod would play next to each other on the left side of the Yankees infield for much of the 10 seasons between 2004-2013, and the two became close, personal friends as well. Jeter was almost exactly one year older, and so the pair were a couple of highly paid, highly publicized superstars playing together in the Big Apple during the entirety of their 30’s.

The two would reach the pinnacle of their playing careers together in 2009 when they would lead the Yankees past the defending World Champion Philadelphia Phillies in the World Series. That 2009 season was one of six in which the pair would lead the Yankees to a 1st place finish in the AL East. It all began to fall apart with the growing revelations of Rodriguez’ use of PED’s, but that is a story for another day.

From 1996-2012, Derek Jeter has not only been a constant as the starting shortstop on the field for the New York Yankees, he has been a leader as well, serving as the team captain since the 2003 season. During that period, the team has won a dozen AL East titles, 7 American League pennants, and 5 World Series championships.

During the bulk of that period, Jeter has mostly been the picture of reliable health. He appeared in at least 148 of the Yankees 162 regular season games during 15 of the 17 seasons between 1996-2012. But he didn’t just “appear”, he excelled. Jeter has proven over time that he is in the conversation for the title of “Best Shortstop of All-Time” in Major League Baseball.

In addition to his Rookie of the Year Award, Derek Jeter has been an All-Star 13x, has finished in the top 10 of MVP voting 7x, and has 5 Gold Gloves. He has a career .312 batting average and .381 on-base percentage over almost 12,000 plate appearances. Never known as a true power hitter or speed demon, he nonetheless has accumulated 256 homeruns and 348 steals, showing that he can beat you with his bat and his legs as well as his glove.

In 2000, Jeter was the Most Valuable Player of the MLB All-Star Game and was that year’s World Series Most Valuable Player. He has won 5 Hank Aaron Awards and 2 Silver Sluggers as the best hitting shortstop, and a Roberto Clemente Award for his contributions off the field to the community.

For the franchise of legends such as Ruth, Gehrig, DiMaggio, Mantle, Jackson and more, Derek Jeter has become the all-time leader in hits, games played, stolen bases, and at-bats while playing in an era of specialty pitching, with much longer travel requirements and closer public scrutiny on the massive public stage that is New York in the age of mass media.

On that public stage, Jeter’s personal life has been magnified. A young, single, attractive star during his 20’s in the 1990’s and his 30’s in the 2000’s, Jeter has been linked romantically with a number of high profile young ladies. It was just reported that he recently broke up with magazine covergirl and Sports Illustrated model Hannah Davis. In 1997 and 1998 he dated superstar singer Mariah Carey, something she has publicly acknowledged.

At various times he had relationships with Miss Universe 2000 and Bollywood star Laura Dutta, Latino singer Joy Enriquez, TV actress Jordana Brewster, TV host (and now Mrs. Nick Lachey) Vanessa Minnillo, Victoria’s Secret model Adriana Lima, fitness model Vida Guerra, and Hollywood actresses Jessica Biel, Jessica Alba, and Minka Kelly. He has appeared on “Seinfeld“, as host of “Saturday Night Live“, and in a couple of motion picture bit parts.

My link with him in the fantasy baseball world began when he was a young player. In the summer of 1998 during his 3rd full season, I became involved with the beginning of a “keeper-style” league that is now about to begin it’s 17th season. At that time, 10 of us drafted from among every player in baseball, and I selected Jeter with my 2nd round choice, the 13th overall pick in that draft. He would be my starting shortstop for the next 5 seasons, leading my Philadelphia Athletics team to it’s first title in 2002.

After dealing Jeter away, I reaquired him for the 2004 season, and then again as a throw-in in a trade prior to last season. He has been a big part of the success of my own fantasy baseball history, and now for 2014 will appropriately go out in our Whitey Fantasy Baseball League with the franchise that for which he began.

The 2014 season will hopefully prove to be a much more fitting farewell for this great player than was his devastating 2013 season. During the 2012 playoffs, Jeter suffered a severe ankle injury. He was able to appear in only parts of 17 games last year as the injury proved much more difficult to heal than was anticipated.

He also watched as his old buddy ARod went through the PED revelations and his own injury troubles, and as the other members of that “Core Four” all made the decision to retire themselves. Posada, perhaps Jeter’s best friend and for whom Jeter stood as Best Man, retired after the 2011 season. Both Pettitte and Rivera retired following last season, Mariano memorably crying on the Yankee Stadium mound when Jeter and Pettitte took him out of his final game.

In addition to these losses and challenges, there have been a number of others. Their longtime manager, Joe Torre, left the Yankees following the 2007 season. Longtime owner George Steinbrenner died during the summer of 2010, as did iconic Yankee Stadium announcer Bob Sheppard. His recorded voice still announces each Jeter at-bat. Derek’s final such at-bat at the stadium will be the final time Sheppard’s voice is heard there after more than a half century.

Derek Jeter is a New York Yankees icon, and a no-doubt first ballot Hall of Famer when he is eligible. We should see his enshrinement at a ceremony in the summer of 2020. He will move into the next phase of his life, possibly in some other role within the game as a broadcaster or coach. Almost certainly we will see him settle down and establish a family of his own.

All reports at this early stage of preparations for the coming 2014 season are positive as far as his health. Let’s hope that he gets to enjoy one last hurrah on the big stage of the big leagues in the Big Apple. If he does, we will all get to enjoy one last year with the man who I personally consider the greatest shortstop to ever play the game, one of the greatest that I’ve ever seen. It’s the end of an era, and let’s all hope it ends as gloriously as Derek Jeter’s legend deserves.


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