Thoughts on the Yankees’ handling of the Sonny Gray dilemma

Relationships fail all the time. Whether it’s a romantic partner, a business and its supplier, or a ballplayer and his club, sometimes things just break down. Over the past few weeks we’ve watched one of those latter relationships decay in an especially notable way, as Brian Cashman has come right out and admitted he’s looking to deal troubled right-hander Sonny Gray before Opening Day 2019.

It’s a far cry from the organization’s confidence in Gray in August 2017. I recently wrote about the sour taste that whole trade is leaving in my mouth, but the situation has really blown up since I wrote that. On Monday Cashman effectively thrashed Gray in a media availability, saying “We are going to move him if we get the right deal because I don’t think it is going to work out in The Bronx”.

Not only is this uncharacteristic of the Cashman we all know (and most of us love), but it’s a curious move for any executive. Most well-informed people within baseball know which players are trade bait and which aren’t. However, it’s awfully weird to have a GM, especially one as well-regarded as Brian Cashman, be so blatant about an upcoming move. To use our relationship example from above, this is the difference between trashing an ex and blocking them on all social media, and simply realizing you didn’t work out together and moving forward as individuals.

Last winter we knew that teams were interested in a deal for players like Manny Machado or Josh Donaldson, but the executives of both teams shied away from statements about the players themselves, deferring to tacit remarks around optimizing return and a focus on long-term strategy. Even this offseason, rumors swirling that Cleveland is open to trading a couple members of their vaunted pitching staff were preceded by comments around “market realities” facing the team’s ownership.

Baseball executives are even tight-lipped when it comes to rapidly toxifying assets. When the Blue Jays shopped Roberto Osuna this summer, even as Osuna was suspended and facing a court date for domestic assault, GM Ross Atkins hammered on the “baseball perspective” side of possible trades, rather than the actual root cause of why the team wanted Osuna out of town. So with all this closed off commentary around possible trades, why is Cashman bucking the trend so hard?

Simply put, he must not see the need for leverage. Tight, controlled public statements keep the power in the seller’s hands. By maintaining plausible deniability, you increase the pressure on the buyer to sweeten their offer. Cashman’s not doing that – he’s forfeited so much leverage by declaring Gray as a must-go asset.

So to me, this means Cashman has enough demand that the extra leverage is negligible. We all kind of scoff at his assurances that there’s interest across baseball for Gray, but maybe he’s right. Sellers require less and less leverage the more their product is in demand, since the market-clearing price will rise on its own to compensate for the demand. Apple doesn’t need to be coy with their new iPhones, demand will always outstrip supply and they can watch the price rise on its own. This has to be the same reality for Gray’s demand – otherwise, why abandon the leverage on the selling side?

Now, Sonny Gray is not going to bring back a Chris Sale-type package, of course. If someone like Corey Kluber or Carlos Carrasco is traded, the return would vastly overshadow a similar price for Sonny. But clearly, Cashman thinks Gray is more valuable than he would appear at first glance. Even if it’s just a couple of teams interested in him, that’s enough to start a bidding war. Don’t hold out hope for a Fernando Tatis Jr – type return, but if and when Sonny Gray is traded, the deal might not be the write off many expect.