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Brian Cashman’s inflexibility is a double-edged sword

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We all know how hyper-disciplined the Yankees GM has been regarding free agency, trades, and player valuations. It has not always been to the team’s benefit.

2019 MLB All-Star Game, presented by Mastercard Photo by Jason Miller/Getty Images

All is too quiet on the Yankees’ front. Ominous news emerged last weekend, as DJ LeMahieu is apparently growing increasingly impatient with being slow-played by New York’s front office. So, he has asked his representatives to re-engage with the clubs that have shown interest in signing him.

Losing LeMahieu would be a huge blow to the Yankees on the field and in the clubhouse, especially now that the best fallback option is off the board following Francisco Lindor’s blockbuster trade to the Mets. If the Yankees are not careful, they could find themselves out a starting second baseman without any palatable recourse to replace him. And it is all a product of Brian Cashman’s inflexibility.

One of the more widely disseminated and discussed topics around these parts centers on action or inaction resulting from Cashman’s hyper-disciplined, at times stubborn approach to free agency, trades, and player valuations. It is both his strongest asset and his most limiting obstacle. It has allowed him to dodge some major bullets, but at the same time has caused the Yankees to miss out on more than a few potentially season-altering players.

The first instance that jumps to mind is Robinson Canó’s free agency. From the time he broke into the big league to his last game played in pinstripes, the star second baseman was the team’s second-most productive player, riding along a Hall of Fame trajectory. Keeping him in the Bronx seemed a no-brainer, reflected by the chorus of fans’ voices.

In the end the Mariners offered around three years and $65 million more than the Yankees’ “lowball” offer, much to the chagrin of the Yankees faithful. But despite several productive years in Seattle and with the Mets, in hindsight it appears the Yankees were rewarded for Cashman’s rigid stance during negotiations. And no, I’m not talking about Canó’s recent PED suspension. I’m referencing the roughly $24 million in available payroll space that is not committed to a 38-year-old second baseman (though it remains to be seen how much if any of that will be spent this offseason).

This rigidity Cashman showed when dealing in the free agent market has not played out to the Yankees’ benefit. Much as he did not want to extend Canó into his forties, Cashman refused to budge on tacking an extra year to the Yankees’ offer to Patrick Corbin, despite the obvious deficiencies in the rotation at the time.

Any justification of not adding that sixth year due to age-related decline at the back end of the contract is specious at best. Especially considering Cashman turned right around and offered a 36-year-old J.A. Happ a deal that had the potential to run into the lefty’s age-39 season. Essentially he extended a player older than Corbin would be at the end of his deal, raising questions as to whether the decision not to sign Corbin was performance-based or purely out of stubbornness on Cashman’s part.

Cashman’s track-record of prospect hugging is just a different manifestation of his inflexibility. The Yankees have had chances to add impact arms to strengthen their championship odds, and have balked at every opportunity. Justin Verlander, Gerrit Cole and Zack Greinke all would have bolstered the rotation heading into the playoffs, but a combination of payroll discipline and over-evaluation of one’s own prospects rendered these potential deals dead in the water.

And speaking of the trade market, Cashman has been particularly inflexible when it comes to his appraisal of the trade deadline. The last two years we have seen the same story: getting back injured players (Luis Severino and Dellin Betances in 2019, James Paxton in 2020) should be viewed as the equivalent of a blockbuster trade. Cashman’s rigid adherence to this narrative is simply not grounded in fact.

Even the way Cashman sets his priorities during the offseason reeks of inflexibility. Last winter, the Yankees suspended all offseason dealings until the Gerrit Cole sweepstakes was resolved. This ended up working in the Yankees favor as it pertains to Cole, however they missed out on the opportunity to bring back fan favorite Didi Gregorius as he opted to head to Philadelphia rather than wait out the Cole dealings.

If this sounds familiar, it is because they are pursuing a redux of the strategy as they handle DJ LeMahieu’s free agency. Cashman has identified LeMahieu as the team’s top priority this offseason, adjourning all other negotiations in the meantime. It could not be going worse for the Yankees, as it appears both sides are separated by contract length and overall value, with LeMahieu growing weary of the front office’s wait-and-see methods. Meanwhile, the Yankees have missed out on a handful of impact players — from the aforementioned Lindor and Carrasco, to relievers Trevor May and Blake Treinen — and instead are content to play chicken with their erstwhile star second baseman.

Cashman’s inflexibility does not extend solely to negotiations. Fans will remember that he acted very un-Cashmanlike at the end of Sonny Gray’s tenure in New York. Following Gray’s rocky 2018 season, the Yankees had every opportunity to delve into why Gray was struggling and search for ways to reinvigorate their young starter back to the budding star that emerged in Oakland. Instead, Cashman insisted Gray could never be successful in New York and became dead-set on trading him.

They got a bag of peanuts for him from Cincinnati, and lo and behold Gray turned into a top-seven Cy Young finisher. Cashman never tips his hand in this fashion, especially when it comes to his opinions of his own players. Thus it appears the trade had nothing to do with Gray’s potential going forward and had everything to do with Cashman petulantly lashing out after he felt he had gotten burned on the trade to acquire Gray.

A more recent, if more innocuous example of Cashman’s inflexible treatment of his players involves Giancarlo Stanton. At the beginning of the offseason, Cashman determined that Stanton would be the full-time DH going forward. Ostensibly, this is to keep him healthy, despite zero provided evidence that playing in the outfield increases one’s injury risks.

Instead, Cashman’s inflexibility in this scenario translates to roster inflexibility. Having a full-time DH limits their ability to use that spot in the lineup rotationally to give other guys a half-day off. Who knows what kind of cumulative effect this can have on the season? At the very least it means they will have to carry an extra outfielder on the bench, further limiting roster flexibility.

Discipline is an indispensable asset for a general manager. Without it, a team’s payroll can balloon with burdensome contracts. However, there is a fine line between discipline and inflexibility. And unfortunately for the Yankees, Brian Cashman’s inflexibility has hurt the team more than it has helped over the last few years.