I feel bad for Brian Cashman. Really, I do. During the 2013 offseason, after the New York Yankees missed the playoffs, Cashman had the go-ahead to spend $438 million on Carlos Beltran, Masahiro Tanaka, Jacoby Ellsbury, and Brian McCann. Over the past three seasons, the Yankees have now played a grand total of one playoff game. On that note, what exactly is the General Manager of a 27-time World Series winner and wealthiest team in baseball to do?

Spend, spend, spend?

No, no, no.

Chasing past performance in Beltran, Ellsbury, McCann, as well as being saddled with the hefty contracts of CC Sabathia, Mark Teixeira, and Alex Rodriguez has provided the Yankees with a large annual luxury tax hit, delivered exactly zero World Series titles since 2009, and has left the team with a hodge podge of aging former stars and a few young players who may one day form the next version of the Core Four. There is no way to win the offseason when the consequence for spending is an increase in the luxury tax, and the downside to not spending is playing out another year as a non-favorite to win the World Series. The stars get older, but also get another year closer to coming off the books.

So far this offseason, Cashman and the Yankees have mostly sat on their hands. The only big move involved dealing a swingman pitcher, Adam Warren, to the Chicago Cubs for Starlin Castro. Aaron Hicks, also acquired in a trade, is not fueling any headlines. Brett Gardner and Andrew Miller were on the block for a time, but there is little chance either will actually be moved before Opening Day. The Yankees cannot really afford to trade either player. Gardner must be kept around to play center field when Ellsbury inevitably falls victim to injury. Hicks and Dustin Ackley are not capable of taking on an everyday role. Miller cannot truly be traded because the team’s one true strength is its incredible bullpen. With Dellin Betances and Miller, the Yankees are essentially able to mask some of the deficiencies in the starting rotation.

This effort to trim payroll and develop young players could not have come at a worse time for the Yankees. David Price, Zack Greinke, Justin Upton, Yoenis Cespedes, Chris Davis, Alex Gordon, Jordan Zimmermann, Johnny Cueto. Any one or two of those players could help to cure what ailed the Yankees last year. Oh, Gardner and Ellsbury went into a massive slump in the second half? Let me introduce you to new Yankees left fielder Justin Upton. There is no consistent presence in the rotation. Try on your new pinstripe jersey, Jordan Zimmermann. This year’s free-agent class is one for the ages, and the Yankees are left to sit it out.

Half of the Yankees fans seem to be at least semi-accepting of the effort to reduce spending and cut down the luxury tax. Signing any big name this offseason would have essentially cost the Yankees 150% of the contract’s value. It makes sense to want to avoid paying $150 million for Zimmermann, $225 million for Upton or Cespedes, or $330 million for Price or Greinke. You can understand that when the numbers are presented to you, but the Yankees have never done business that way. It becomes a very difficult pill to swallow, watching the Arizona Diamondbacks and Chicago Cubs leap into action and sign players who could potentially be Yankees.

On the flip side, waiting for prospects to develop is even harder. Aaron Judge may never turn into a serviceable Major League starter. He’s a 6’7″ outfielder who still has plenty of issues hitting Triple-A pitching. You can’t trade him, however, because you’ve committed to the process of developing the farm system and allowing prospects to reach the big leagues. Rob Refsnyder would seem to be one of those prospects, but he is now blocked by Castro. The Yankees had to deal away an arm that performed very capably in a fill-in role as a starter last season to even get Castro (who comes with plenty of his own questions), and still have not been able to address the holes in the rotation. There’s no trading of Judge, or Gregory Bird, or Luis Severino, however, because the Yankees are now fully committed to allowing them to at the very least reach the big club.

The Yankees neglected their own farm system for years, preferring to target free agents. There has not been much to show for it, however. A franchise that spends like the Yankees should not be happy with one World Series title since the year 2000. It’s not supposed to work that way. Money kept being thrown around until it became unsustainable, no matter how expensive tickets in the moat behind home plate are. The Yankees now have a new stadium with some of the most expensive tickets in baseball, a frustrated fan base unaccustomed to watching a team that will have to scrap for 85 wins, no real hopes of contending for a World Series, and an aging roster with some prospects who might, might be All-Stars. As it is, very few franchises follow the old-school model for roster building. The Boston Red Sox “won” the offseason last year by signing Hanley Ramirez and Pablo Sandoval. One more last place finish should be enough to show that throwing gobs of cash at free agents with murky pasts is not the way to go. It’s a tough lesson to learn, but it has finally sunk in.

Every move the Yankees could make this year is a Catch-22. Trade Gardner for young pitching, wait with baited breath for your center fielder to go down. Sign Justin Upton to play left field, fork over a huge tax penalty. Go forward with the roster as currently constructed, hope for the best, and perhaps miss the playoffs for the third time in four years — unheard of for the Yankees. No matter what Brian Cashman does this offseason, there is a huge downside risk to every move. This is not how the Hot Stove season is supposed to go for the New York Yankees. Money is supposed to mask all weaknesses.

Unfortunately for the Yankees, the lesson in New Age roster construction has sunk in at precisely the wrong time. There are actually free agents under the age of 30 on the market this year — the type of players that would have helped jump start the Bombers. The Yankees need to get younger, and easily could have with a Justin Upton or Jason Heyward. Financial constraints placed on the front office by years of poor, reactionary decision making, however, turned the 2016 offseason into a no-win situation for poor Brian Cashman.

About The Author

Joshua Sadlock

Josh is a lifelong baseball and Orioles fan. He grew up in Harrisburg, PA, home to the Senators, the AA affiliate of the Montreal Expos and now Washington Nationals. Josh's highest aspiration in life is to one day retire from his civil engineering career and become a beer vendor in Camden Yards. In one career varsity baseball at-bat, he went 0-1 with one strikeout. Follow @JoshSadlock on Twitter, or email josh@baseballessential.com

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2 Responses

  1. fbluhm

    Cashman’s eyes tell the story – a man of frustration who would have liked to have done more, but was told he couldn’t.

    Reply
  2. David Galster

    I realize the rules of the land have changed since George Steinbrenner rulled the team. I am hoping that once some of these onerous contracts are off the Yankee books, Hal will again revisit the free agent market. However, I am sure he will be youth concious and not fall into the trap of signing aging players already in their thirties to long term contracts. I know it sticks in his crawl everytime he has to pay the mlb luxury tax and I don’t blame him.

    Reply

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