Yankees reach historic crossroads at trade deadline

For the first time since 1992, the Yankees have reached a philosophical crossroads. Sure, there have been bumps in the road, but for the past twenty-four years very few existential questions have been asked of America’s most illustrious sports team. Right now, that is changing, as the Yankees face the daunting quandary of selling their most recognisable veterans at the trade deadline.

How George Steinbrenner changed the Yankees

This is a franchise defined by winning. Twenty-seven World Series titles, forty American League pennants and fifty-two postseason appearances attest to that. The Yankees won with Babe and Lou, Joe and Mick, Reggie and Thurman, Derek and Mo. They won in times of war and eras of peace, with superstars and replacement players, veterans and kids. News of Yankee championships has been delivered by telegram and radio, newspaper and internet. It’s who they are. It’s what they do. Success is not only demanded in the Bronx, but it is expected.

“Winning is the most important thing in my life, after breathing,” said George M Steinbrenner III, that archetypal Yankee owner. “Breathing first, winning next.”

That became the Yankee Doctrine, the ethos by which every pinstriped team lives and dies. In fact, the notion of winning at all costs dates back to 1915 and Colonel Jacob Ruppert, the Yankees’ first great architect. It was Ruppert who bought Babe Ruth from the Red Sox. It was Ruppert who built Yankee Stadium, the first triple-decked ballpark in America. And it was Ruppert who demanded glory from his expensive roster.

The Yankees actually suck

So, with such a historical investment in winning, what happens when the Yankees lose? What happens when the future is far more uncertain than the storied past? What happens when the stands are half-empty and the heir to Derek Jeter may not even be born yet?

For the first time in a generation, we’re experiencing this unique situation, as the Yankees actually suck. Once a popular chant in ballparks from coast to coast, it was typically laced with jealousy amid the dynasty years under Joe Torre. But now, there’s some factual validity to the notion, as a constitutional crisis brews at the corner of 161st Street and River Avenue.

The Yankees are currently 40-42 on the season, good for fourth place in a lacklustre American League East. New York is seven games behind division-leading Baltimore, and a 10-17 mark against Eastern opponents doesn’t inspire much confidence. As for the Wildcard? Well, the Yankees are even four and a half games adrift of the second berth, which essentially leaves them with limited hope of playing deep into October.

On this date last year, the Yanks were 44-38, only to fall back after the All-Star break before losing to Houston in the play-in game. In 2014, their mark was 43-43 at this juncture, but the farewell tour of Jeter created the illusion of glory and inspired Brian Cashman to trade for upgrades. This time around, even a mid-season spree may not save this faltering incarnation, as selling assets becomes the most logical alternative.

Inside the Yankees' demise

In all honesty, hope has been fading among Yankee fans for almost four years now. Allowing Robinson Cano, the next franchise icon, to join Seattle was seen as a watershed moment. The team has haemorrhage talent in the ensuing years, and a fleeting playoff game last year was secured only after miraculous production from Mark Teixeira and Alex Rodriguez.

Last winter, Hal Steinbrenner didn’t spend a cent in big league free agency, preferring instead to double down on continued excellence from two ageing anchors of an ordinary lineup. But Teixeira has battled numerous injuries and is currently hitting .192, while Rodriguez has been relegated to platoon-DH status following a dismal start to his age-41 campaign.

The Yankees have received great contributions from Carlos Beltran and Didi Gregorius, and Masahiro Tanaka is still an ace, but the team’s one pronounced strength, it’s dominant bullpen trident, is of minimal utility without adequate run support or a mid-game bridge.

The result has been a frustrating team that treads water slightly below .500. Indeed, the Yankees are on pace to finish 79-83, which would be their first losing season since '92 and just the twenty-second in franchise history, dating all the way back to 1903.

In the later days of George, such a scenario would have been unthinkable. Managers would have been fired and prospects would have been traded. That managerial style is no longer conducive with winning, as young talent has become so precious in a period of greater financial parity, but the emotion that guided it is sorely missed at Yankee Stadium.

Why don't the Yankees spend money anymore?

I’m sure Hal is tired of hearing it, but the general perception is that he lacks the intense desire to win that so defined his father. The owner will argue that there is a plan in place, and I’ve wrote about Aaron Judge and the new Yankee core on several occasions. Yet that strategy hopes to deliver sustainable, long-term success for a franchise and fanbase that demands immediate gratification. That doesn’t make it inherently wrong, but the rich and powerful Yankees should never find themselves with such a lack of talent. That they do speaks solely to the failure of Hal and Cashman, not to mention Randy Levine.

Some people argue that the modern Yankees are cheap. Half a billion dollars spent on ordinary players like Brian McCann and Jacoby Ellsbury would suggest otherwise, but there is certainly a reticence to spend with the frequency of yore. The Cano ordeal was followed by a failure to sign Yoan Moncada, a prized international prospect who appeared to fit the Yankees’ rebuilding plan. Then came last winter, when the Red Sox added David Price and the Mets signed Yoenis Cespedes while the Yankees stood pat, hoping to coax a playoff run from a deeply flawed roster.

Many experts say the Yanks are trying to create payroll flexibility for a run at Bryce Harper in 2019, but they don’t need to save up! They’re the New York Yankees. They charge a fortune for tickets and generate extreme amounts of revenue. There’s enough money there to put a championship calibre team on the field every single year. Choosing not to is exactly that: a choice. And that goes against everything the Yankees are supposed to stand for.

As a consequence of past intransigence in the free agent market, the Yankees have created an awkward situation for themselves. This winter, the market is incredibly poor, unless you want to build around Josh Reddick. Yes, young prospects like Judge, Luis Severino and Gary Sanchez may graduate to the big leagues, and several heavy contracts expire this fall, but I just don’t know if there’s enough talent there to compete for a World Series title right away. The return of Greg Bird will be a major positive, but possible solutions for restoring the Yankees to greatness are otherwise diminishing fast.

Should the Yankees sell at the trade deadline?

The one route back to serious contention in 2017 and beyond is to sell veteran assets in return for young commodities this summer, which already appears doomed. The Yankees certainly can’t raid their farm system to seriously upgrade this month, otherwise a black hole will appear in the organisation for years to come. It’s not in the Yankee DNA to sell, and they haven’t done so during a season since 1989, but desperate times call for drastic measures. It’s time for change.

Even selling veterans has pitfalls that are often overlooked. Prospects can fail, and attendances would likely fall further as a team of even less quality is initially placed on the field. But this is the problem Yankee executives have made for themselves, and they’ll have to bite the bullet. The team’s record at developing and managing young talent has also been questionable for at least a decade, but at this point what can be worse than watching Aaron Hicks play right field? Not much.

The Yankees could get a very strong haul for Andrew Miller, the bullpen ace tied to a very generous contract. Several contenders yearn for relief help, and the Yankees could target players like Javy Baez on the Cubs or Joey Gallo of Texas. Furthermore, Aroldis Chapman should net a solid prospect or two, despite being a rental attached to the stigma of domestic violence charges. Elsewhere, Dellin Betances would also fetch some pieces that can help the Yankees push the needle back towards contention.

Here’s another overlooked reason why the Yankees should absolutely break up their bullpen: several elite relievers are available in free agency this coming winter, affording them the opportunity to replenish almost immediately. Kenley Jansen, Sergio Romo, Jonathan Papelbon, Junichi Tazawa and Chapman are just some of the hurlers New York could pursue next winter, and Cashman has always been tremendous at building bullpens. In a hypothetical scenario, the Yankees would undoubtedly be much improved in 2017 with Gallo, Baez, Jansen and Chapman than they would be with Betances, Miller, Chapman and the same tired lineup that has failed so readily this year. A lot would need to go right for that to become reality, but there needs to be a clear vision as to what the Yankees are trying to accomplish from here on out.

Cashman should also try to move Beltran before his deal expires. The outfielder is hitting .296 with 19 home runs this year and would be one of the premier bats available on the summer trade market. While his age, health and rental status may reduce the return, teams such as Cleveland and Kansas City may enter a bidding war, boosting the price a little. It’s at least worth having those discussions, just as it is worth listening to offers for Ellsbury, Brett Gardner and any other major leaguer not named Tanaka, Castro or Gregorius.

Perhaps the Yanks could even find playing time for Judge, Sanchez and Severino in the second half, allowing them to develop without the burning pressure of a pennant race. Who knows? They may even play well enough to keep the winning season streak alive.

Yankees' trade deadline strategy

Ultimately, the Yankees haven’t faced such a dilemma in almost three decades. Some say they should have traded Cano at the deadline in 2013, but I disagree. Mariano Rivera was still the closer and Jeter was still around, although injured. Back then, the Yanks were still clearly in win-now mode, even if it didn’t work out. Likewise with the chatter surrounding David Robertson in 2014. That was a different era; an era which already seems so long ago for the Yankees. Now, there is little reason to expect a revival from the current roster, both in the immediate, medium and long term future. Therefore, the only route back to prosperity and away from mediocrity is to sell, even if it contradicts every philosophy on which this team is built.

There’s something admirable about the Yankees’ unwillingness to tear it all down and start over. I’ve never been totally okay with teams tanking for lengthy periods. But as some point, this team must do the logical thing and move on.

Fangraphs currently gives the Yankees just a 7% chance of reaching the postseason. In Yankee Land, where qualifying for the playoffs was once a foregone conclusion, that constitutes failure on a grand scale. So, at the very least, the top brass should look to salvage something from the smouldering wreckage, and that something should be young talent acquired for established veterans, as plans to build a new core are expedited.


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