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Do the Yankees have the prospects to trade for Luis Castillo?

The Yankees’ farm likely could sustain a Castillo trade, but don’t expect Brian Cashman to pull the trigger anytime soon.

Milwaukee Brewers v Cincinnati Reds Photo by Joe Robbins/Getty Images

The rumor de jour this last weekend centered on Reds pitcher Luis Castillo and the Yankees. After the Yankees made good on their first rumored targets, DJ LeMahieu and Corey Kluber, it seemed eminently possible that they’d follow through on the latest whispers.

Talk has died down, particularly at the report that the Reds asked for Gleyber Torres, and potentially more, in exchange for Castillo. As I said in Monday’s writeup of the news, moving Torres for Castillo is a likely nonstarter from the Yankees’ perspective, at least in terms of pure value. The two both project as roughly four-win players in 2021 per FanGraphs’ calculations, but Torres is younger, further from free agency, and plays a less risky position. Any Torres-for-Castillo deal should involve extra talent coming the Yankees way.

The potential exchange got me thinking about if the Yankees could pull off a Castillo deal without having to trade away a big league starter. Could they do it just with prospects? The Yankees’ farm still has talent, even as it’s thinned, but could it sustain a blockbuster on its own?

The short answer: yes, any decent farm system can pull down a good player if you’re willing to part with a large number of prospects. But that brings us to our longer answer. The shape of the Yankees’ system at the moment means that Brian Cashman would have to surrender a ton of sheer volume for Castillo. Cashman doesn’t make those kinds of deals. If push came to shove, the GM might just reason that the team’s farm couldn’t sustain the blow a Castillo trade would deal.

Let’s look at the particulars. Castillo’s value is a little difficult to pin down, as he has a surprisingly short track record of just 90 major league starts. However, he has looked dominant over the 44 of those starts that came across the last two seasons, running a 140 ERA+ and 10.9 K/9 over that span. Castillo is 28, three years from free agency, and probably among the 20 or so best starters in the game.

We do have precedent for dealing for a pitcher of Castillo’s caliber. Two or three years before free agency is often the sweet spot for deals involving stud hurlers. In-prime, effective starters are obviously coveted, but any team that has one locked down for a half-decade or more is loath to part with him under virtually any circumstances. A bit closer to free agency, and the price comes down enough that interested teams can at least dream of matching the ask, while the selling team can still get enough to convince themselves to part with their ace.

I think a good place to start is with a trade that hits home: the Yankees’ 2017 midseason deal for Castillo’s current teammate, Sonny Gray. At the time, Gray wasn’t quite the pitcher Castillo was now, but he was a 27-year-old brand-name starter with a 122 ERA+ when the Yankees acquire him.

Cashman surrendered Dustin Fowler, Jorge Mateo, and James Kaprielian for Gray, all consensus top-100 guys at the time, but none of them truly excellent prospects. If Gray represented trading for 2.5 years of a good pitcher, Castillo represents three years of a great pitcher. Gray fetched three good names, and it stands to reason Castillo would fetch more.

We can look to other trades to gauge how much more. In fact, the recent Blake Snell tells us plenty. Snell is more expensive than Castillo, but has a similar pedigree and stands three years from free agency. The Padres traded an elite prospect in Luis Patiño, solid prospects Blake Hunt and Cole Wilcox, and young but inconsistent big leaguer, Francisco Mejia.

That feels more representative of what a Castillo deal would require. Three quality prospects, with one being a true blue-chip, with maybe another player with major-league potential thrown in. Other examples show a similar format. Chris Archer, 2.5 years from free agency, actually cost the Pirates two blue chips in Tyler Glasnow and Austin Meadows, plus Shane Baz. Jose Quintana, 3.5 years from free agency, cost the Cubs Eloy Jimenez, plus Dylan Cease and Matt Rose.

The ask for a blue-chip prospect is where things would get tricky for the Yankees. Unless the Reds are higher than most on Jasson Dominguez or Deivi García, the Yankees don’t exactly have a premium prospect. They have good ones, for sure, but they don’t have a great one, at least not at this exact moment.

To make up for the lack of a consensus elite prospect, Cincinnati would almost certainly ask Cashman to compensate with a wealth of good prospects. The Yankees would probably have to include four of their top six or seven to get the deal done. They might also need to throw in someone like Domingo Germán or Miguel Andújar to fill the role Mejia played in the Snell deal.

Without straying too far into the fantasy land of fake trades, such a trade could entail Dominguez, at least one, if not both, of García and Clarke Schmidt, plus multiple other interesting players, perhaps from the team’s stable of middle infielders, and Germán. So, back to the long answer. The Yankees clearly have the prospects to make the trade, but the kind of five-for-one, offer-you-can’t-refuse deal that’s required is precisely the kind of swap Cashman just rarely makes.

I know I personally feel more aggressive about swapping prospects for big-league talent than some GMs. If I could run the Yankees for a day, I almost definitely would grab Castillo if I could do it without touching the team’s starting lineup, relying on prospects like Dominguez, Schmidt, and two or three more decent prospects to get it done. If the Reds required both García and Schmidt, along with Dominguez and others, that’s where I’d feel less sure, and probably opt out of this dream scenario so that I could let Cashman start making the hard decisions again.

At the end of the day, a lot comes down to the trading team’s preference. If the Reds just aren’t enamored with the Yankees’ farm, there’s not much for the sides to do except for the Yankees to reject Cincinnati’s advances on Torres and move on. That said, history shows us what it typically takes in prospects to get a player as good as Castillo. The cost is one the Yankees can pay, but it would take a chunk out of the top of the farm. For that reason, and for better or worse, expect Cashman and Co. to pass.