What the Jameson Taillon and Luis Castillo trade talks tell us about the Yankees

In the aftermath of the DJ LeMahieu and Corey Kluber signings, the Yankees made it clear their offseason wasn’t finished. Even with “priority number-one” completed, the team immediately was the subject of trade rumors, particularly regarding Luis Castillo. Most of us scoffed when those rumors ultimately died down at the Reds’ suggestion that the Yankees would need to send Gleyber Torres in return, though Peter made an impassioned case that those rumors weren’t so crazy.

After the latest Castillo-to-the-Yankees saga concluded, I found myself considering Brian Cashman’s recent track record on the trade market. I never viewed the Castillo idea very seriously, simply because it seemed that Cashman would be far more likely to move on a player like Castillo after the 2021 season, not before it.

With three years of team control remaining, and a median projection as one of the 20 best starters in baseball, Castillo is a fantastically difficult trade target. Teams don’t surrender those kinds of talents without feeling they’ve received an offer they can’t refuse. After 2021, with Castillo then just two years from free agency and getting more expensive (in the dehumanizing parlance of the modern front office, after his “surplus value” has decreased significantly), it’s far easier to envision Cashman making a competitive trade offer.

Indeed, glance at some of the Yankees’ most prominent trades of the last half-decade, and the GM’s MO looks obvious. He doesn’t make opponents offers they can’t refuse. The Yankees will gladly exchange larger groups of decent prospects, but they won’t yield on their true blue-chip talents in order to snag the most premier names on the trade market.

Consider the Sonny Gray trade back in 2017. Two and a half seasons of a good pitcher cost the Yankees Dustin Fowler, James Kaprielian, and Jorge Mateo. It was a fairly deep package of prospects, but one that featured solid talents, not excellent ones.

After the next season, James Paxton came into Cashman’s sights. Once more, two years of a good pitcher. That cost the team Justus Sheffield, Erik Swanson, and Dom Thompson-Williams. Sheffield was a very nice prospect, ranked in the top 50-to-60 range ahead of 2018, and Swanson had a strong 2018, but again, the Yankees managed to swing a deal for a good but non-premium trade target in exchange for good but non-premium prospects.

The Yankees’ other trades don’t fit so sweetly into this “two-ish years of a good pitcher” paradigm, but they still further the overall theme. The 2017 deal that brought back David Robertson, Todd Frazier, and Tommy Kahnle took the decent but unspectacular package of Blake Rutherford, Ian Clarkin, and Tito Polo. The 2018 rentals of Zack Britton and J.A. Happ cost even less, with the veterans on the precipice of free agency.

That all brings us to the Jameson Taillon trade. With this swap, we have the most prime example yet of Cashman and the Yankees’ standard procedure with regard to trades. Taillon has high-end talent, but with just two years left prior to free agency and big injury concerns, his price came down into the Bombers’ range. Voilà, Taillon was made a Yankee for, you guessed it, a package not at all dissimilar to the ones that brought back Gray, or Robertson/Kahnle.

The transition from the Castillo pursuit to the consummation of the trade of Roansy Contreras, Miguel Yajure, Canaan Smith-Njigba, and Maikol Escotto for Taillon just feels like the quintessential modern Yankee front office at work. They looked at the pie-in-the-sky target in Castillo, drew their line in the sand, and walked away when it was clear they’d have to cross it. They retreated to the target they knew they could snare in Taillon, packaging the kinds of prospects they know they can replace.

It’s a line of thinking that should be familiar to many readers of this site. It’s parallel to the team’s reported attitude in the free-agent discussions of 2018, with Manny Machado and Patrick Corbin, and it also harkens back to the Justin Verlander trade talks in August of 2017, among others. The Yankees know what they’re willing to do, and are so seldom convinced to exceed it. They do so only on rare occasions for especially rare opportunities, such as the chance to sign a super ace like Gerrit Cole as a free agent.

I’m sure I’m not alone in finding this type of management frustrating at times. At some point, as a fan, I want the team to just go for it, and push some real chips into the middle of the table to try to push this team over the top (though one could argue that the Cole signing was the push-all-the-chips-in maneuver).

At the same time, Cashman’s MO does at least have some merit. Many years ago, some may have thought that he was too stingy in reportedly refusing to hand over Luis Severino and Aaron Judge in a potential blockbuster deal for Jason Heyward and Andrelton Simmons. It’s certainly a relief that this trade never came to pass. In a broader sense, it’s a relief that Cashman never put many of the Yankees’ blue-chip young guys on the table, whether it was Judge and Gary Sánchez, Torres and Clint Frazier, and now, perhaps, Deivi García and Jasson Dominguez. The Yankees do deserve some credit for seemingly knowing which of their young talents to hold tight to, and which to jettison.

This analysis has focused on the trade market, where I’d argue the team’s work has on the whole helped the roster quite a bit over the past four years. It sets to the side the matter of the free agent market, where there’s little defense for the Yankees’ refusal to make more all-in maneuvers that exchange money for wins, at a time when a few wins could move the needle from “potential favorites” to “champions.” That’s a topic for another day. For now, it’s possible to find Cashman’s attitude about trades both annoying and, to this point, beneficial for the team’s chances.