How Brian Cashman Unwittingly Dug The Hole The Yankees Are In

Brian Cashman, Yankees GM (Photo: Boston Globe)

The tone of Hal Steinbrenner’s recent comments has been apologetic to Yankees fans. Cashman is the one who needs to step up, though…

Hal Steinbrenner has signed off on player expenditures for the 2019 season which leaves the Yankees payroll for players at $220 million, well above the luxury tax limit of $206 million. If this figure holds, the Yankees will pay a 20 percent tax after the season amounting to about $3 million.

The additions of Adam Ottavino and DJ LeMahieu can be blamed as the culprits, but in reality, the Yankees fate was sealed some time ago with the signing of Jacoby Ellsbury and the rush to judgment trade for Giancarlo Stanton.

Giancarlo Stanton, New York Yankees (Photo: Sports Illustrated)
Giancarlo Stanton, New York Yankees (Photo: Sports Illustrated)

The Yankees have a problem with money, and it’s going to get worse before it gets better. For some fans, they are immediately turned off and tuned out when they hear or read something like that, but it’s true. These fans get confused, thinking the conversation is about cash flow, a problem the Yankees will never have. And they can’t quite grasp the fact that merely having the money (to spend) is not a valid reason to pay it.

Readers will recall I touched on this theme a few days ago. The accent (then) was on future Yankees payrolls when the full thrust of the Baby Bombers reaches adulthood with expensive arbitration settlements and, ultimately, the free agency of players like Aaron Judge, Luis Severino, James Paxton, and Gary Sanchez.

And so it came as no surprise to hear Hal Steinbrenner almost apologizing for the Yankees gun-shy stance in not aggressively pursuing either Manny Machado or Bryce Harper this offseason, despite the fact either player was born to wear Pinstripes. Steinbrenner used these words to explain his predicament with the Yankees, of all teams, giving the appearance of being “cheap”:

“Fans should keep an open mind that I’m never done until I’m done, and that’s usually not until Opening Day,” Steinbrenner said. “Proposals come to me every day with these guys, between the analytics guys and the pro scouting guys, and I’m going to consider every single one of them.”Katherine Acquavella,

Words like that are a foreign language to Yankees fans who have been spoiled over the years by an always open cash register. Need a player to drum up interest in the team again? No problem, Roger Clemens, Randy Johnson, Alex Rodriguez, Mark Teixeria, Jacoby Ellsbury, Giancarlo Stanton…sign right here on the dotted line and welcome to the New York Yankees. Until of course they are no longer welcome because they’re not pulling their (payroll) weight.

Brian Cashman’s Error In Judgment

Brian Cashman has been idolized many times in this column. But perhaps it’s time to recognize that he’s made a colossal error in judgment over the last few years. Cashman has become the master of trades. His legacy and lore are chronicled in articles like this one, in which lists Cashman’s “Six Most Remarkable Trades.” Countless other stories support the same theme.

Gerrit Cole, Free Agent 2020 Photo Credit: Sporting News
Gerrit Cole, Free Agent 2020 Photo Credit: Sporting News

But along the way, Brian Cashman and the Yankees have lost sight of the need to plan for what’s coming in the free agent market. When Cashman had Derek Jeter on the phone discussing the Stanton trade, for instance, how far forward was his thinking in realizing that both Harper and Machado were up only one season after Stanton became a Yankee? And did Brian Cashman think through the extended consequences of taking on the remaining portion of Stanton’s contract ($275 million)?

Did Cashman see Nolan Arenado, Gerrit Cole, Chris Sale, Madison Bumgarner coming in 2020?  Was he looking at the 2021 crop of free agents, which is set to include Mike Trout, Mookie Betts, James Paxton, and J.T. Realmuto? Or, was he thinking that the Trade Master strategy would carry the team through?

The Yankees Moving Forward

Unless they want to shoot the luxury tax out of the sky with an “Ah, the hell with it” attitude, the Yankees hands will remain tied until the contracts of Ellsbury and Stanton are dealt with, and preliminary decisions are made regarding their own expensive crop of free agents.

Can/Should they expect, for instance, to sign long term deals of five years or more with Didi Gregorius, Dellin Betances, Judge, Aroldis Chapman, Sanchez, Paxton, Aaron Hicks, et al.? Or, will the team need to cherry pick, deciding the two or three they want to keep and pay them accordingly to stay. The cliche applies – the Yankees can no longer have their cake and eat it too.

To their credit, the Yankees have continued to put a winning team on the field every season during their rebuilding and salary restructuring years. Unlike, for instance, the Phillies and Astros, who “tanked” for a few years to get high draft picks, thus building up a reservoir of salary money to eventually spend on free agents.

Jacoby Ellsbury, Yankees Occasional Outfielder (Photo: New York Post)
Jacoby Ellsbury, Yankees Occasional Outfielder (Photo: New York Post)

Soon, Ellsbury will be a memory. But Stanton will never go away unless he opts out in 2021, of which there is about the same chance Ellsbury will play in 120 games for the Yankees in 2019. The Trade Master will need a miracle to trade either of them, but Cashman needs to make an effort. Both Stanton and Ellsbury are made for the West Coast where teams like the Giants, Dodgers, and Angels bleed almost as much money as the Yankees.

The Angels, in particular, would seem to be a good fit for Stanton. Mike Trout wants to play for a winner, and with the addition of Stanton, he might be inclined to agree to an extension with the Angels rather than entering the free agent market in 2021. Add a few pieces from there, and Arte Moreno, the owner of the Angels, would be enticed into making the trade, as opposed to looking up at the Astros for the next decade.

It’s Complicated

Mistakes of the past are not easy to erase. We all know that from our experience. The Yankees and Hal Steinbrenner’s decision to run the team like a business, as opposed to a hobby, is honest and straight forward. As fans of the Yankees, we need to accept and respect the team’s decision to not throw money at Harper and Machado’s demands.

Besides, as I’ve argued before, this is a Yankees team that has enough to win it all. A tune-up in July is always in order, but for now – let ’em take it as far as they can with what they have.

And in the meantime, after all these years as the GM of the team, Brian Cashman may not be looking too far down the road, but the Yankees are. Trades are lovely as a way to build a team, but they are also often shortsighted (Paxton is only guaranteed to be here for a year), as opposed the engaging the free market for deals in the five to six-year range.

The Yankees missed the boat for 2019, but with better planning that doesn’t need to be the case forever.

Written by Steve Contursi, Editor, Reflections On Baseball
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Author: stevecontursi

I am an amateur writer with a passion for baseball and all things Yankees and Mets.

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