When the New York Yankees drafted Derek Jeter in 1992, the 18-year-old shortstop entered an organization with a cloudy future. Over two decades later—through no fault of his own—he'll exit New York with the Yankees staring down an uncomfortably similar fate.
During Jeter's reign in the Bronx, the Yankees dominated the sport. Led by a resurgent farm system, the core of a dynasty was erected in the mid-'90s.
Despite experiencing October failure throughout most of the 2000s, no franchise has been more successful since the day Derek Jeter became the shortstop in New York.
Despite the cloudy future that hovered over the Yankees when Jeter was drafted, the outlook changed quickly and swiftly thanks to factors such as Gene Michael reviving the farm system, Buck Showalter nurturing young, ascending talents like Bernie Williams, Mariano Rivera and Andy Pettitte, Joe Torre arriving as manager and George Steinbrenner's hefty wallet.
As with any franchise, times change.
Jeter is still around, but the faces and symbols of his most successful years are long gone.
From Steinbrenner's death to Torre's awkward parting to age and attrition breaking apart a dynastic core, the Yankees changed considerably as Jeter transitioned from superstar to solid contributor.
Now, as Jeter embarks on his farewell tour in 2014, the future of the organization is as murky as it was the day the all-time-great shortstop arrived.
In fact, due to a win-now edict, poor farm system and imperfect leadership options, projecting how the Yankees will look over the next five years—both aesthetically and in the win column—is a fool's errand.
If the post-Jeter future in the Bronx were up to some Yankees fans, a rebuilding effort would commence in 2015 and beyond.
Due to the immense pressure to win a World Series every single season, the Yankees won't allow themselves to traverse down that type of path. That was proven this winter when the team blew past their self-imposed $189 million salary cap in order to procure talent to reach the postseason.
On the surface, signing Jacoby Ellsbury, Brian McCann and Masahiro Tanaka to lucrative, long-term deals is a great way to improve a team that limped to an 85-win finish last summer.
Yet, without some help from the farm system, the Yankees will be unable to field a consistent winner over the next five years.
Unfortunately for a franchise that built a dynasty based on homegrown talent, impact players are not on the horizon for 2014 or the foreseeable future. During a three-part series on the Yankees farm system, Andrew Marchand and Wallace Matthews of ESPN New York took a look at the issues surrounding New York's inability to produce stars.
When asked about the state of the system, Brian Cashman was blunt in his assessment.
"It's not as good as we need it to be in terms of results," Brian Cashman said. "There are a number of reasons behind that. At the end of the day, we've had some misses, without a doubt. We've had some guys who didn't make their projections, who failed to cross the finish line. So basically it's fair to criticize where we're currently sitting."
Unless you believe in Michael Pineda's shoulder, Manny Banuelos' elbow or J.R. Murphy's catching ability, the Yankees are going to have to spend in free agency to replace Jeter and the rest of their aging roster over the next few years.
While money is rarely an object for this franchise, the long-term payroll sheet is far from clean. In 2015, the Yankees already owe over $148 million to nine players—including a mind-boggling $22 million to Alex Rodriguez, per Cot's Baseball Contracts.
Eventually, money will come off the books and new stars will arrive, welcomed to New York with glitz and glamour.
The team will only have $86.1 million on the books when the 2016 season concludes. As Chris Cwik of Sports on Earth points out in this free-agent primer, that winter's class of available stars could include both Giancarlo Stanton and Stephen Strasburg.
Regardless of the cost, the Yankees will find talent. A fertile farm system could sustain success for much less money, but the team doesn't have that luxury right now.
Beyond procuring talent in the years after Jeter's retirement, a major leadership void could emanate in the Bronx.
Jeter's captaincy has been a constant for the Yankees for years, but the veterans surrounding him—from Jorge Posada to Mariano Rivera to Andy Pettitte—all shared a similar trait: They came through the system.
Prior to this winter, Robinson Cano was the logical choice to be the next leader of the Yankees. Not only was the star second baseman great; he was a Yankee from the day he arrived in America. Upon signing a $240 million contract to play in Seattle, Cano's opportunity to become Jeter's heir apparent in the clubhouse disappeared.
Now, for the first time in a long time, the next Yankees leader will likely be a mercenary. Yes, a former free-agent signing must ascend to the throne of clubhouse enforcer. This winter, Brian McCann arrived in New York with a reputation as a fiery leader from his days in Atlanta.
Owner Hal Steinbrenner didn't mince words about McCann's best traits, per Daniel Barbarisi of The Wall Street Journal.
"He's a very smart guy, and he knows that this is Derek Jeter's clubhouse," said Steinbrenner. "And he's said that. But I think naturally he's a leader, and that comes out. It's just a matter of time."
Steinbrenner may be right about McCann, but another catcher actually represents the best in-house option for the transition away from Derek Jeter's captaincy.
According to Joel Sherman of the New York Post, manager Joe Girardi, a former catcher and teammate of Derek Jeter, is the bridge that will link this era of Yankee baseball to the next successful run.
"Thus, even in Jeter’s farewell tour, Girardi becomes more important than ever. For in 2014 and beyond, he will be the link to this recent glorious past, the one most responsible for maintaining the Yankee Way. He must keep the standards and win totals high," Sherman writes.
Sherman, while undoubtedly correct, stumbles upon some of the future issues within this organization.
Girardi, a legitimately excellent manager, is the bridge to that gap and deserves to be given power within the club. Yet, the team needs an on-field leader to emerge in order to sustain long-term success.
In a perfect world, that leader will be cultivated through the farm system, nurtured by Girardi and allowed to flourish on the field and in the clubhouse.
That formula—great organization, excellent manager, history of stars—was perfected by the St. Louis Cardinals. As Albert Pujols' reign ended, Yadier Molina's began. Both learned under the tutelage of Tony La Russa.
The Yankees aren't the Cardinals. If they were, Jeter's departure would just be a grand farewell on the path to bigger and better things.
In this case, it's not. When Derek Jeter retires, an organizational shock could overtake the Bronx. Not only will the Yankees need to replace a shortstop; they'll need to carve a new identity and rethink a long-term plan for success.
Brian Cashman and Joe Girardi, much like Gene Michael and Buck Showalter in the early '90s, are smart enough to navigate through this transition. Now comes the hard part: actually doing it.
Will the Yankees struggle without Derek Jeter?
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