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The Next Yankee Dynasty Is Closer Than You Think

The 2017 Yankees may not seem that exciting at first glance, but they might just be a prelude to the next great run of teams in the Bronx.
Kim Klement-USA TODAY Sports

It's been nearly eight years since the New York Yankees have won a World Series. For the vast majority of Major League Baseball clubs, this is not a long time to wait. We just saw the Chicago Cubs win their first in over 100 years. There are seven franchises that have never won one, and two of those—the Seattle Mariners and the Montreal Expos-turned-Washington Nationals—have never been to the World Series at all.


For the Yankees, however, those eight years must have felt like an eternity. After all, this is the sports franchise. Twenty-seven rings. Count 'em. There have been longer droughts, but those felt shorter because they were either competing for a World Series or because of their high-priced stars and off-field drama. After all, this was the organization that George Costanza worked for.

And that might be the oddest thing about the New York Yankees of today. Not only are the Yankees not likely to be a World Series contender in 2017, they aren't all that glamorous or interesting, either. They still have plenty of players with big salaries, but a large portion of those players are declining (C.C. Sabathia) or haven't come close to meeting expectations (Jacoby Ellsbury). By and large, the Yankees really haven't been a big factor in free agency lately, although they did spend big money on re-signing Aroldis Chapman and modest money on Matt Holliday this year.

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No, the current big-league version of the Yankees is not particularly exciting. They still have Brett Gardner. But that's about to change. (Not the Brett Gardner part, necessarily.) We may soon be looking at the next New York dynasty.

The Yankees have built a flourishing, sustainable farm system without tanking or lowering their payroll, and have set themselves up for another great roster built on homegrown talent.


"It's almost weird," a National League front-office member said. "You think of the Yankees as this empire that buys whatever player they want, but that hasn't been them for a few years now. There have been times where you've expected them to move some of their top prospects as a stop-gap, but they've held steady. I'm sure it's frustrating to their fans, but it could pay big dividends for them down the road."

The reason the Yankees' future looks so bright is because they have SO many upper-echelon talents that they aren't willing to trade. A few years ago, their farm system was ranked in the middle of the pack. Now they have one of the very best groups in baseball, ranking second on ESPN Senior Baseball Writer Keith Law's top system rankings for 2017, up 11 spots from 2016. How has the system gotten so good so quickly? Two things: process and luck.

From 2007 to 2012—a period where there were some excellent draft classes—the Yankees' top picks that they signed were Andrew Brackman, Jeremy Bleich, Slade Heathcott, Cito Culver, Dante Bichette Jr., and Ty Hensley. It probably goes without saying, but none of these players are projected to be contributors going forward, and outside of Hensley, all were considered reaches at the time.

In Dellin Betances, the Yankees have one of baseball's best relief pitchers. Photo by Anthony Gruppuso-USA TODAY Sports

The last few years, however, the Yankees have drafted as well as anybody. Last year they drafted Blake Rutherford (18th overall pick), an outfielder Law ranks 22nd overall on his top prospects list. The previous year, they drafted James Kaprielian (16th overall), a right-hander from UCLA who Law ranks 28th on his list. In 2013, they drafted Aaron Judge with the 32nd overall pick (42nd on Law's list), and Eric Jagielo with the 26th pick, who was a key component in the trade that brought Chapman to New York last year.


"A night and day difference," an American League executive said. "There must have been some financial decisions based on some of those selections in the earlier part of the decade, because some of those selections were guys that we didn't have close to that range, with all due respect to some of the guys that were making decisions at that time. It's too early to tell if some of these [guys] are going to work out, but they sure seem to be getting it now."

In addition to an improved draft strategy, the Yankees have also been active spenders in the international free agent market. In the summer of 2014, the Yankees were given a $2.2 million allocation to sign international free agents. Going over that figure would result in paying significant taxes. In a class filled with high-upside talents, the Yankees spent more than $14 million in bonuses, and had to pay close to double that figure in taxes. All this for players who are usually going to take at least four to five years before they sniff the big leagues.

So both the draft and the international free agent market has helped restock the farm system, but perhaps the biggest reason why the Yankees have the top system in the American League has to do with being in the right place at the right time. Rewind back to the summer of 2016. Several teams in contention prioritized acquiring bullpen arms. And the Yankees, who in the middle of the summer still had an outside shot at making the playoffs, possessed two of the very best relief pitchers in baseball in Chapman and Andrew Miller. Eventually, the Yankees turned those two bullpen arms into six prospects, including the current crown jewel of their farm system, shortstop Gleyber Torres, who came over from the Cubs as part of the Chapman deal.


"If you saw this kid play in the Arizona Fall League (where he was selected the Most Valuable Player), you would be convinced he was the best hitting prospect in baseball," said the A.L. executive. "He can hit for average, he can run, and he can really go get it in center field…. The Cubs are great at this stuff, and Chapman was a key cog for their championship, but to get a guy like that for a rental closer? Wow."

Aside from the Torres deal, the Yankees sent Miller to the Indians in exchange for Clint Frazier, an outfielder with a bad haircut but some of the best bat speed in the minor leagues; and Justus Sheffield, a southpaw who can miss bats with three pitches. Those deals all but ensured that the Yankees were not going to make the playoffs in 2016, but probably assured the team long-term success beyond that.

Young outfielder of the future Aaron Judge looms over outfielders of the past Jacoby Ellsbury and Brett Gardner. Photo by Kim Klement-USA TODAY Sports

The 1996-2000 Yankees are the last dynasty in baseball. In hindsight, you might remember that team being filled with high-priced free agents. There was certainly some of that, but the core of the team was filled with guys who were signed and developed by the Yankees. Derek Jeter? Homegrown. Bernie Williams? Homegrown. Mariano Rivera? Homegrown. Andy Pettitte? Homegrown. Jorge Posada? You get the picture. Even important players who weren't originally with the team like Tino Martinez and David Cone were acquired in trades using some of that homegrown talent.

Without getting too far ahead of ourselves, that's something the Yankees are well positioned to do going forward. They already have quality young players like Gary Sanchez and Greg Bird. Assuming you're not talking to team president Randy Levine, they still possess one of the top young relievers in baseball in Dellin Betances. He'll likely be joined in the bullpen by Luis Severino at some point, and that should be a formidable 1-2 punch behind Chapman when they're ready to compete. Didi Gregorius is a quality shortstop, and when Torres is ready to come up from the minors, they can either move Gregorius to second, or trade him for more quantity and quality. There is a potential quality prospect or quality young player at every position. How many other clubs can say that?


And when these young players are ready to come up and contribute, the Yankees will begin to lose some of their high-priced players. Over the next four years, the Yankees will see C.C. Sabathia ($25 million), Chase Headley ($11 million), Starlin Castro ($16 million), and Jacoby Ellsbury ($21 million) come off the books. You might consider the Yankees an ATM with no limit, but it's a lot easier to spend money on quality free agents when you're not paying average players high salaries. Soon, Bryce Harper will become a free agent, and there are rumblings he will demand a $400 million contract. Will any team be in better position to pay Harper than the Yankees? Mike Trout will hit free agency the year Ellsbury's contract expires. Is it hard to imagine Trout playing next to Harper in the outfield?

"They're not going to be down for long," the AL executive said. "They're really set up for long-term success. Even though they haven't really been players for the big free agents the last years, you know that if a guy like Harper or Trout or Kershaw or whatever hits the market, they're gonna be all over it. You better get your licks in now."

It's easy to dismiss farm systems and spout cliches like "prospects fail," but if you're paying close attention, you know that this is how great teams are built. Just look at what the Cubs have done. Same for the Astros. Same soon for the Braves. Will the Yankees need to have some things go right? Of course. Is it easier to hedge those bets when you know you're one of the top markets in baseball? You better believe it.

The Yankees are likely to miss the playoffs again this season, but in a couple of years you should remember that the groundwork for their success was laid down when the product seemed boring. Sometimes, even the very rich need to take a step back and conduct some honest self-assessment to take steps forward. Even the Yankees.

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