I started watching baseball at a very young age. I'm not old enough to remember Derek Jeter's Rookie of the Year campaign in 1996, but I tuned in soon after. I grew up several hours from New York City, but often saw vanity plates like "2JETER2" on the country roads of my upstate home. My parents and much of my family embraced the "Evil Empire" perspective of the Yankees, but even so, we felt the shortstop had an unimpeachable dignity that commanded respect. Years later, it doesn't surprise me that the 39-year-old and his diminished abilities are about to bow out of professional baseball, yet I can't help but feel shaken by the news. Derek Jeter's retirement is about more than Jeter himself; he is the last remaining piece of a baseball Golden Age. As much as fans will delight in watching a legend take one final stab at a sixth World Series, his impending departure magnifies the struggles of a once-dynastic franchise that is failing to adapt to a changing baseball landscape. In the late 1990s, players like Jeter, Ken Griffey Jr., Cal Ripken, Chipper Jones, Pedro Martinez, and Randy Johnson achieved near-mythical status among fans, and their appeal extended to non-fans as well. Even relief pitchers, typically baseball's most anonymous and least consistent players, got in on the stardom. Mariano Rivera and Trevor Hoffman, arguably the two greatest closers in baseball's history, enjoyed sustained periods of dominance during this era. It was truly an embarrassment of riches for Major League Baseball, a league packed full of talented players who had personalities to match. For all of baseball's Jeters, Griffeys, Ripkens, there were the McGwires, the Sosas, the Bondses, and the finger-wagging Palmeiros (dear God, let us never speak of the Cansecos,) equally talented and dynamic players whose careers were marred by allegations or admissions of steroid use. Players like these help to explain why fondness for Derek Jeter runs so high: he evokes the best qualities of the nineties baseball boom, without any of the cheating or rule-breaking baggage that puts a damper on the nostalgia. With one glaring exception, the Yankees avoided association with the steroid era's most notorious characters, but Major League Baseball's crackdown on performance-enhancing drugs has played a part in the hard times they have endured since their last championship in 2009. As Alex Rodriguez's recent turmoil has demonstrated, performance enhancers are still a factor in the big leagues, but the strict implementation of suspensions has muted their effect. This means that position players can no longer be counted on to put up big numbers well into their thirties. Major League Baseball requires a minimum six years of service before a player can file for free agency, which means that most star players become eligible to make a splash in the open market around the ages of 28 to 30. Prior to the 2011 season, at age 29, left fielder Carl Crawford signed a seven-year, $142-million contract with the Red Sox. He was coming off statistical highs in 2010; he had an OPS of .851 and swiped 47 bases for the Rays. The following year, his OPS plummeted to just .691, and he stole safely just 18 times. Crawford in one in a long list of players who have faltered after emerging from free agency with a huge contract. In the same season, 32-year-old Jayson Werth's OPS dropped a staggering 200 points after he signed a $126 million deal with the Nationals. His production has since rebounded, but he has missed nearly 120 games over his last two seasons with Washington. Slugger Adrian Gonzalez seemingly lost all ability to hit for power when he signed a $21-million-per-year contract with the Dodgers at age 30; in two seasons and about 750 at-bats with Los Angeles, he has hit 25 home runs, with just three coming last season. In their first and second seasons with new teams, respectively, big-name hitters Josh Hamilton and Prince Fielder managed mediocre production that fell well short of their pay rates. Both players will be earning over $20 million per year until they reach age 36. In looking at these players, and others who have struck it rich in free agency over recent years, it is evident that most of them achieved their peak statistical seasons between the ages of 25 and 27, typically before they are eligible for a new contract. This is not to say that a late-career renaissance is impossible for any player, but not since Barry Bonds has a position player managed to so thoroughly defy the challenges of age. None of this is good news for the Yankees, who consistently rely on their deep pockets to secure free agency's hot commodities. This offseason, they landed Jacoby Ellsbury, whose story seems disconcertingly similar to that of Carl Crawford, or even Johnny Damon, who failed to live up to expectations after defecting from Boston in 2006. Free agent pitchers tend to be more able to produce into their thirties, but the Yankees have struggled to target good pitchers in free agency, most notably when they signed 31-year-old Jose Contreras for $32 million over four years in 2003. Japan's Masahiro Tanaka seems like a good bet, but the 25-year-old has logged at least 150 innings of Japanese baseball over each of the past seven years, and his stratospheric pitch counts give pause to those who remember the truncated careers of Mark Prior, Brandon Webb, and Dontrelle Willis, the latter of whom spent most of last season pitching for the independent Long Island Ducks. In the aftermath of the steroid era, quality farm systems, smart trading, and lower-risk free agent signings have been increasingly bigger factors in building successful MLB teams. The emergence of very young superstars such as Bryce Harper and Mike Trout may allow teams such as the Yankees to acquire some peaking free agents a few years down the road, or these players may just continue the trend of peak years occurring early. In any case, the discombobulated Yankees need to realize that lucrative signings will not guarantee the championships that they guaranteed in the past. In so many ways, homegrown talent Derek Jeter exemplifies how to get it right.