“The Captain” Parts 5 & 6 | The Emergence Of MLBbro Derek Jeter, Mr. November

“It’s A B**ch Playing In New York” | The Captain, Part 5

 “Its a bitch playing in New York. It’s not easy. I’d like to think my relationship with the media was a good one.  I didn’t try to make their job difficult. I tried to make my job easier.  This was how I was going to survive New York.” – Derek Jeter, episode 5 of The Captain.

By 2004 the New York Yankees and Boston Red Sox were meeting for the second straight year in the American League Championship Series and took a 3-0 lead.

Previously there had never been a team who blew a lead that large in a best of seven series.  The Yankees took a 4-0 lead in game four and were looking to finish them.

“There was no doubt in my mind that the series was over,” recalled Gary Sheffield.

Sheffield, part of the new generation of Yankee imports at the time,  was acquired following their second late inning meltdown that cost them a world championship in 2003.

After years of dominance, New York felt no pressure and there was an arrogance it would continue. Even with new actors on stage it was Cats or the Lion King on the Bronx version of Broadway.

Despite knowing the outcome you want to see a production with a different cast. However, the absence of chemistry and pressure from the Red Sox proved too much in 2004.

Jeter had previously stated in episode four of The Captain that there were “ghosts in Yankee Stadium that would show up” and despite acknowledging the Red Sox were a good team “they were still the Red Sox and they would find a way to choke.” This time it didn’t happen.

  “You can tell when pressure is getting to people especially when they haven’t been in situations like this before,” Jeter said.

For the first time in his career Jeter’s team couldn’t find the clutch gene that would have sealed another pennant.  After the team’s meltdown he felt the heat from the organization.

General manager Brian Cashman started using analytics which were concluding that he no longer had the range to be the spectacular defensive shortstop such that his contemporaries were.  Alex Rodriguez and Nomar Garciaparra.

George Steinbrenner, the notorious owner who was known to admonish players and managers for not playing up to the championship standard that trademarked the organization, made the bold move to empower Jeter.  After talking with fellow pinstripe legends such as Reggie Jackson and Willie Randolph Steinbrenner officially named Jeter the 11th captain of the Yankees.

 “There’s nothing I did as captain that I wouldn’t do if I wasn’t the captain,” said Jeter.  “In order to maintain a consistent level on the field, my job as captain was to limit the distractions with our team.”

With the ascension came the New York media’s voracious appetite for Jeter’s personal life.  From Esquire Magazine to the New York Post’s Page Six, the analysis of his dating life and cultural background became headlines.    Rumors of gift bags for dates after the proverbial happy ending took a life of their own once they were published above the fold.

Nobody did a better job of hiding in plain sight than Derek Jeter,” said veteran baseball writer Joel Sherman.

An ESPN interview between Sheffield and a longtime reporter also brought issues of race into the Jeter legacy. When “Sheff ” stated the Yankees Black and white players were coached differently and Jeter “wasn’t all the way Black”, Pandora’s box of bi-racial conversation  suddenly became in play with the media.

“Derek Jeter does not identify racially,” said longtime New York sports pundit Wallace Matthews. “He just seemed to be racially neutral.  Derek Jeter was almost colorless.”


 “How I was raised was as a Black man,” Jeter said. “That’s how society is going to view you.”

Regardless of color, Jeter played the entire fame game in The Big Apple as well as anyone to ever do it.

The Captain — Part 1

“The Captain” Pt 1 | The Early Years Of Derek Jeter, Understanding His Place In America

The Captain — Part 2

“The Captain” PT 2 | Derek Jeter Becomes King Of New York

The Captain — Part 3

“The Captain” Part 3: “I Never Got Along With People Who Were Cocky Or Arrogant”



“The Captain” Part 4: Transformation Complete: Jeter Becomes 11th Yankees Captain

“The Captain” Part 4: Transformation Complete: Jeter Becomes 11th Yankees Captain

“When you win four [world championships] in five years where are you going after that. There’s nowhere else to go. You’ve got to stay there or you waste a year of your career.” – Derek Jeter

Following 9/11, the emotional aftermath took it’s toll on the New York Yankees as Jeter became the 11th captain in the team’s history.

That was just one part of the transformation that started taking place in early stages of the twilight of his career.  The powerful championship machine that was seemingly invincible began showing signs of falling apart despite being five-time American League championships  and winning four World Series.

To the outside observer, the Yankees were a juggernaut and the original group who redefined their legacy in the Bronx were beginning to show signs of age.

With age came the experience and championship savvy which held over from their previous success.  However, the grind of annual postseason lore and the dramatic finishes began wearing on a dynasty in transition.

“If you play this game long enough you’re going to struggle,” Jeter said.  “It gets hard.”

Part of what made the Yankees of the Jeter era so iconic was the fact they would never die, the opposition had to kill them.  But in many respects the annual grind of more than a half decade of postseason title runs began wearing them down.  They had become the championship fighter who could no longer deliver the knockout blow when it came time to close.

However, the routine of ALCS comebacks and ultimately playing until November left the aging Bombers in a place they were unaccustomed to. Mariano Rivera, the greatest closer in the baseball history, blew saves against the Arizona Diamondbacks in 2001 and the Florida Marlins in 2003 and their invincibility was no more.

After their final late inning meltdown on the precipice of a championship, the core of Camelot would be torn apart.  A Yankees team that was previously built through drafted players who were developed through their organization succumbed to a new era of free agent players that were brought in for immediate success. The influx of imported teammates which changed the dynamics inside their clubhouse.

That was the time when Jeter started seeing his baseball mortality. Many of the names on the locker would change because team owner George Steinbrenner was adamant about winning another before turning the franchise over to his son Hank.  Ultimately, however, the Boston Red Sox had different ideas.

“The Captain” Part 3: “I Never Got Along With People Who Were Cocky Or Arrogant”

“The Captain” Part 3: “I Never Got Along With People Who Were Cocky Or Arrogant”

“I never got along with people who were cocky or arrogant. I’m confident in my ability but not arrogant.  I have a small group of friends who are like family to me. It takes a long time for me to trust someone. If they do something or slights me in any way, I have the unique ability to just cut them off.” – Derek Jeter, Captain.

Coming off their 1998 world championship, the New York Yankees started looking more like general manager Brian Cashman’s team than the one Bob Watson built.  Roger Clemens was signed during the offseason and other free agents such as Chad Curtis, there was a change in the atmosphere of the clubhouse.  

Jeter admitted that he didn’t like Clemens from previous incidents where the Rocket hit or flirted with his central casting chin by delivering 100 mph fastballs with precision. However, Jeter respected Clemens because “he was a gamer” and would show up every to every start ready to compete.

Curtis, however, was from a totally different world. They were an oil and water mix.  Former Yankees catcher Jorge’ Posada remembered how Jeter’s blasting hip hop music rankled the feathers of Curtis and “that rubbed him the wrong way”. Their tempered feud came to a head during a heated benches clearing brawl in Seattle when Felix Rodriguez hit Curtis. During the melee’ Jeter and Alex Rodriguez appeared to be exchanging pleasantries while Curtis took a beatdown.

“First off Chad Curtis has issues with everybody,” Jeter said.  “This [wasn’t] the first time I had an issue with Chad Curtis.  It was the first one that people found out about.” 

With a gangsta grin and disarming warmth, Derek Jeter opens episode three of “The Captain” with a look into the soul of what made him great.  Like other great champions such as Michael Jordan and Kobe Bryant, who were affable outwardly, Jeter’s quest to be a champion was driven by things which may have been mundane to most. 

In a December 2000 article with Esquire Magazine, Alex Rodriguez, Jeter’s ride or die MLB homey, answered a question from reporter Scott Raab about Jeter’s “character amongst players”.  A-Rod’s answer would change their relationship forever.

“Jeter’s been blessed with great talent around him, so he’s never had to lead,” Rodriguez said.  “He doesn’t have to. He can just go and play and have fun and hit second. Hitting second is totally different than hitting third or fourth in a lineup because you go into New York trying to stop Bernie [Williams] and O’Neill and everybody.

“You never say don’t let Derek beat you.  That’s never your concern.”

That was also the same sentiment that was shared by Boston Red Sox shortstop emeritus Nomar Garciaparra.  After the Yankees beat them in the 1999 American League Championship Series with Jeter delivering a home run in the clinching game Garciaparra said the 

 “We didn’t lose to the better team,” Garciaparra remembered.  “We just weren’t good enough to win the series.

Jeter’s response nearly two decades later: “That’s what losers say”.

Neither Rodriguez or Garciaparra ever reached his status on the field or off it either. While they took moments to exhale Jeter “never enjoyed the moment because he a was preoccupied by “what’s next next.”

Jeter then won the 2000 World Series MVP after leading the Yankees to their fourth championship in five years when they beat the New York Mets 4-1.

“The Captain” Part 4: Transformation Complete: Jeter Becomes 11th Yankees Captain

“The Captain” PT 2 | Derek Jeter Becomes King Of New York

“The Captain” rolls into its second episode with the story of how Derek Jeter had matured and was ready to become the catalyst to the reemergence of a proud franchise. Behind the hazel eyes and boyish good looks, he opens up about how he took the mantle of team leader.

“I’m very loyal as a person and a player,” Jeter said.  “But loyalty one way is stupidity.  When I feel like you’re trying to take advantage of me I’m done.” 

He braced for the real chance of being demoted had it not been for an injury to his predecessor Tony Fernandez which he says is the only reason he wasn’t optioned to Columbus to start the 1995 season.

“In 1995 my name was the subject of a lot of trade rumors,” Jeter, who was Minor League Player of the Year at the time, recalls.  “My manager Billy Evers called me and told me to splash some water on my face and come to his room early in the morning and tell me congratulations you’re going to the big leagues.”

He wasn’t active for the playoffs but was in the dugout for the 1995 American League Division Series which they lost to the Seattle Mariners.  By 1996, Jeter was front and center as the leadoff hitter and solidified them as a championship team. He, Bernie Williams, Jorge Posada, and Andy Petite were blossoming into cornerstones of a dynasty and the stage was a perfect hit for him.

Jeter arrived with Joe Torre as the new manager after the Yankees cleaned house in the front office and installed Bob Watson as the team’s new general manager.  Jeter felt pressure and thought he was heading back to Columbus until the incumbent shortstop Tony Fernandez broke his arm two weeks before spring training ended.

“I always loved playing in front of people, period,” Jeter said.  “I don’t care if you were a scout or a fan.  I felt like I was performing and the more people the better.  It gave me a chance to show off.  Everybody’s watching now, right!”

After the first World Series victory in 1996, Jeter became “King of New York” and was the toast of every borough, especially The Bronx and Manhattan. Within 36 months of bringing a championship to the Bronx, Jeter was the A-list celebrity whose moves were being chronicled by Page 6. His entourage included hip hop icons such as Sean “P. Diddy” Combs, and Spike Lee who were as enamored by his talent as he was to be around them.

Jeter talks openly about his discipline and focus and how Don Mattingly taught him how to be a professional on the field. However, it was Darryl Strawberry, who had his problems navigating his social life as the young player with the New York Mets, who became his off-field mentor that gave him knowledge of a night life griot who blew his chances for the Hall Of Fame by making moves off field that diluted his play on it.

The complicated relationship with Alex Rodriguez is exposed and Jeter candidly explains how their relationship went from good friends to past tense. The Yankees were a championship team while A-Rod was a myth because he was playing in Seattle where many fans on the east coast never saw him play on TV because of the time zone difference.



That Jeter was photographed for the cover of Sports Illustrated posing with his arms around the neck of Rodriguez contributed to this narrative that their friendship was eroding. A-Rod’s blunt comments about being a better player than Jeter also helped fracture ties between the two generational shortstops, especially after Jeter led the Yankees to two World Series in three years, but most experts still branded the Mariners phenom as the best player.