Yankees Facing Most Important Trade Deadline of the Brian Cashman Era

Zachary D. Rymer@zachrymerMLB Lead WriterJuly 28, 2016

Yankees GM Brian Cashman faces his ultimate test in the next few days.
Yankees GM Brian Cashman faces his ultimate test in the next few days.Jim McIsaac/Getty Images

Including this one, the New York Yankees have been winners in each of the last 24 seasons. That's meant 24 years of buying or staying the course at the trade deadline, as one does when one is a winner.

So go figure that doing the opposite before the August 1 deadline is exactly what the Yankees need now. This is a franchise in need of a turning point, and only by selling will it find it.

Brian Cashman, a key player in the Yankees front office since 1992 and general manager since 1998, took a step in that direction with the trade of fireballing closer Aroldis Chapman to the Chicago Cubs. After a quarter-century's worth of deadline moves with only the short-term future in mind, this could be merely the first in a series of moves with the club's long-term future in mind.

But for the moment, that's not a given.

A full-on fire sale seemed inevitable when the Yankees dropped their first two games after the All-Star break. But they've since won eight out of 11 to climb to within four games in the American League wild-card race.

"Anything can happen in baseball," first baseman Mark Teixeira said Tuesday, per Andrew Marchand of ESPN.com. "A lot weirder things have happened. If we get hot, we can play with anybody, but we just need to keep grinding away."

NEW YORK, NY - JUNE 27:  Mark Teixeira #25 of the New York Yankees celebrates his seventh-inning home run against the Texas Rangers at Yankee Stadium on June 27, 2016 in the Bronx borough of New York City.  (Photo by Jim McIsaac/Getty Images)
Jim McIsaac/Getty Images

The bosses may be on Teixeira's side. A recent report from ESPN.com's Wallace Matthews claimed Cashman and the Yankees front office want to sell but that owner Hal Steinbrenner and the other suits aren't yet ready to detach from the ol' George Steinbrenner edict to win no matter what.

From the sound of things, they haven't yet changed their minds.

"I have a green light to continue to do my job, which is to assess market values both coming and going and make recommendations, and [Hal will] tell me what he wants done," Cashman said, per Marchand. "Then I'll execute as told."

Ross D. Franklin/Associated Press

The idea that the Yankees should still go for it is a defensible position. Chapman was aiding the Yankees bullpen with a 2.01 ERA and tons of strikeouts, sure, but he's also a free agent-to-be who was superfluous next to Andrew Miller and Dellin Betances. Trading him didn't fundamentally change the team, which is indeed still alive in the AL playoff picture.

But in reality, the Yankees are "still alive" like the Black Knight was still alive in his fight with King Arthur in Monty Python and the Holy Grail

Entering Wednesday, Baseball Prospectus and FanGraphs put the Yankees' chances of making the playoffs around 10 percent and of winning the World Series at half a percent. Because a still-terrific bullpen is flanked by an offense with the AL's lowest OPS and a starting pitching staff with the AL's ninth-best ERA, it's hard to say these figures underestimate the Yankees.

If they stay defiant and go for it, the Yankees won't actually be abiding by the franchise's proud history of chasing championships. They'll only be sticking to the more recently established tradition of mediocrity. They'd be asking for a fourth straight season without a postseason victory.

Taking the alternate route wouldn't be painless. The actual end may have already come, but the Yankees admitting defeat will certainly feel like the end of an era. You can already hear the takes about The Boss spinning in his grave.

What should not be forgotten, though, is that it was when the Yankees' late owner was out of the way that the foundation for the club's best years was built.

During Steinbrenner's three-year ban from baseball from 1990 to 1993, a front office led by Cashman and Gene Michaels cultivated a core of young players that included Derek Jeter, Jorge Posada, Bernie Williams, Andy Pettitte and Mariano Rivera. The rest, as they say...well, you know the rest.

NEW YORK - NOVEMBER 04:  (L-R) Andy Pettitte #46, Jorge Posada #20, Derek Jeter #2 and Mariano Rivera #42 of the New York Yankees celebrate with the trophy after their 7-3 win against the Philadelphia Phillies in Game Six of the 2009 MLB World Series at Y
Pool/Getty Images

The list of quality homegrown players the Yankees have developed since then is frighteningly short, consisting only of Robinson Cano, Brett Gardner, Betances and a few others. Rather than developing their own stars, the Yankees have spent the better part of the last two decades buying and trading for stars developed by other teams.

In fairness, this used to work. There's no arguing with five World Series and seven AL pennants between 1996 and 2009. But in today's MLB, this approach just doesn't fly anymore.

As Rob Arthur showed at FiveThirtyEight, the notion that baseball's star power is skewing younger is no mirage. And for good reasons. More young players have grown up playing baseball exclusively. And without performance-enhancing drugs, veterans just don't age like they used to.

You can't count on young players landing on the free-agent market, and an environment such as this one makes them tough to pry away in trades. That means the best way to build a winner is to be like the Kansas City Royals or Chicago Cubs and build one from the ground up. 

The Yankees aren't totally unaware of this. Hal Steinbrenner made a point of wanting to rebuild the club's farm system in a 2013 interview with Daniel Barbarisi of the Wall Street Journal. Credit is owed to him and Cashman for following through as much as they have since then.

Four Yankees prospects made it into Baseball America's latest top 100: shortstop Jorge Mateo (19), catcher Gary Sanchez (36), right fielder Aaron Judge (42) and right-hander James Kaprielian (99). They got shortstop Gleyber Torres, the No. 27 prospect, in the Chapman trade. The other two prospects in the deal, outfielders Billy McKinney and Rashad Crawford, have too much talent to be called mere throw-ins.

However, this is only a good start.

In the coming years, the Yankees need to worry about restocking a lineup with only two players (Didi Gregorius and Starlin Castro) under the age of 32 and a starting rotation that features only one guy (Masahiro Tanaka) controlled beyond 2017.

The upcoming free-agent markets aren't going to help the Yankees do this. The next free-agent bonanza won't come until the winter of 2018-2019, when guys like Bryce Harper and Jose Fernandez are due to headline maybe the most star-studded winter market in history.

The Yankees' best play is to load up their farm system as best they can, graduate as many young players to the majors as possible within the next two years and then use their riches to add impact veteran talent to a team already loaded with young up-and-comers.

If the Chapman trade was one step in that direction, it's now time for the others. Carlos Beltran, another free agent-to-be, should also go. Bolstered by two more years under contract, Miller's trade value is too high for him to be deemed untouchable. Gardner, Michael Pineda, Nathan Eovaldi and Ivan Nova look like trade chips too. Guys like CC Sabathia, Brian McCann and Chase Headley may not be immovable.

Collectively, that's a big pile of trade bait that could net the Yankees a big pile of prospects while also saving them a decent pile of cash. If that's what they end up with, that's how they'll know they're rebuilding the right way.

It would indeed feel like the end of an era. But what the Yankees must understand between now and August 1 is that this might be the start of an entirely new era that, in time, could be just as good as the old one.

    

Stats courtesy of Baseball-Reference.com and FanGraphs unless otherwise noted/linked.

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