The Yankees’ Path Forward

On Saturday night, the Astros ended the Yankees season with a 4-0 shutout. For New York, even reaching Game 7 of the ALCS was a surprising accomplishment, as this was a team widely considered to still be in rebuilding mode heading into 2017. As a young team who became a good team faster than expected, the easy comparisons are to teams like the 2015 Cubs or the 2008 Rays, and expectations for the 2018 Yankees are now going to be particularly high given the team’s success this year.

And the Yankees are certainly setup well for the future. With Aaron Judge, Gary Sanchez, and Greg Bird, they have three enviable offensive building blocks for the middle of their order, and plenty of quality all-around performers like Didi Gregorius and Aaron Hicks, plus the potential upside of Clint Frazier and Gleyber Torres. And that’s just the young hitters. Few organizations in the game have a similar kind of talent base to build off of going forward.

But, similar to the Cubs, there are some legitimate questions on the pitching side of things, and a winter of inaction while counting on the kids to develop further and carry the team to the 2018 World Series is unlikely. The Yankees are both extremely well positioned for the future, but also need to do some real work this winter.

With CC Sabathia set for free agency and Masahiro Tanaka’s postseason raising the potential of an opt-out, the rotation is the biggest area of concern going forward. Luis Severino and Sonny Gray are a nice start, and Jordan Montgomery looks like a solid back-end starter with some upside remaining, but that’s three arms in an area where you want seven or eight. Between Tanaka (if he opts out, which I’m guessing he will), Sabathia, Michael Pineda, and Jaime Garcia, the team has 82 starts and roughly +6 WAR heading to free agency this winter.

Re-signing either or both of Sabathia and Tanaka is an option, of course, but with the team attempting to get under the $197 million luxury tax threshold, their preference may be to sign free agents for more years at a lower AAV, and neither Sabathia nor Tanaka are guys you’re going to necessarily want to extend for long periods of time.

If Tanaka opts out, the team would be heading into the winter with roughly $130 million committed to 14 roster spots, assuming Erik Kratz is their only non-tender from their arbitration eligibles. That gives them a little under $70 million to spend in AAV while staying close to the luxury tax, but a chunk of that has to be used for the pre-arb guys who round out the roster and they’ll likely want to save some room for mid-season acquisitions, so the winter budget is probably closer to $60 million.

If Tanaka opts out in order to get an extra year or two on his deal, and they wanted to bring him back, it seems likely his AAV would be in the $20 million range; maybe a little more or less depending on whether he settles for four years or pushes for five. Sabathia, I would guess, is probably looking at something like 2/$30M this winter; John Lackey got 2/$32M from the Cubs for his age-37/38 seasons, for reference. So bringing back both of those guys probably takes up about $35M of the ~$60M the team might spend this winter.

Or, if the front office believes they could fill one of those two spots more cheaply, they could combine the money that it would cost to bring back both of those guys into a bigger offer for Yu Darvish, hoping that helps Shohei Otani pick New York as his destination this winter. But, like I said in the Cubs write-up, it’s likely that a few teams are thinking about the sign-Darvish-and-hope-it-gets-you-Otani plan, so Darvish might end up being pretty expensive, and Brian Cashman has made it clear he prefers to stay away from long-term deals for guys in their 30s these days.

So while the Darvish-and-Otani plan might sound the most appealing, it’s also the one they have the least control over, and they could end up in a weird position of having money to spend and no one to spend it on if they wait for resolution on that front and end up not getting either one. Thus, I’d think it’s probably in their best interests to try and retain Tanaka.

His elbow certainly presents some risk, but he’s probably their best chance to get a guy you’re comfortable starting in October at a low enough AAV to give them room to add multiple other pieces as well. If they have to choose between Sabathia at $15M AAV and Tanaka at $20M, even if they’d get Sabathia for fewer years, I think Tanaka might be the better buy, since he could provide some postseason value that you’re probably not going to get from Sabathia.

Assuming one of the two leaves, they’ll likely need to trade for another depth starter or two. Even if they give Chad Green another shot at starting, they’d still be short on guys who could keep the team’s rotation solid if one of the primary starters goes down, so I’d expect the Yankees to be looking to add a starter who has remaining minor league options. And those are usually controllable young guys, which aren’t easy to acquire.

But if the Yankees want to add another depth arm who they can keep at low salaries for the next few years, they have a pretty decent trade chip in Dellin Betances to try and get that kind of guy. Betances’ exit from New York has looked inevitable since last year’s spat over his arbitration filing and the ridiculous public comments made by Randy Levine. With a deep bullpen full of high-octane arms, the Yankees can spare Betances, and he may very well prefer to go to an organization that will give him a chance to pitch in higher leverage situations and not publicly criticize his attempts to get paid for his work.

He certainly didn’t help his trade value by posting a 17% BB% this year — or issuing walks to five of the 19 batters he faced in October, when he was relegated to mop-up work when his control couldn’t be trusted — but he still has one of the best arms in baseball, and a team that thinks it could get him straightened out would likely still be interested in acquiring his final two years before he reaches free agency. The Pirates, for instance, have made a habit of acquiring hard-throwers with strike problems for years, and with depth of young starting pitching, perhaps there’s a deal to be made.

On the position player side of things, the primary questions are at third base and DH. Chase Headley is still under control for one more season and Gleyber Torres is expected to return from his Tommy John surgery in time to compete for the third base job at some point in the spring, so the Yankees have internal options, but with a hole at the DH spot, there’s room to bring a guy like Todd Frazier back if the team so chooses. But, like Sabathia, Frazier isn’t a guy you want to sign long-term, and he’s probably not looking to take a pay cut, so he might be a better fit for a team that isn’t concerned about the AAV-effects on their luxury tax calculation.

Instead of bringing back Frazier on a short-term deal, perhaps they should instead make a run at Carlos Santana, a significantly better hitter who probably won’t get a massive contract as a DH headed towards his 32nd birthday. Adding a switch-hitter who doesn’t strike out that much could deepen the team’s line-up — I like Didi Gregorius too, but you probably don’t want him hitting between Judge and Sanchez forever — and give the team a nice alternative to the type of hitters they are primarily building around. Signing Santana would signal that the team is mostly committed to Gary Sanchez behind the plate, but they could still play Santana at first base against lefties if they wanted to give Sanchez some DH time occasionally.

A Tanaka/Sabathia/Santana trio of signings probably eats up most of the money the team would have to spend this winter, but if they only retain one of their two starters, they’d have room to bring in Santana and still make another upgrade or two. Perhaps that is using Starlin Castro to get someone to take a chunk of Jacoby Ellsbury’s remaining contract, then signing a guy like Neil Walker to take over at second base. Perhaps it is making a trade for a guy like Matt Carpenter to upgrade third base, shifting Torres over to second base, where his skillset is a bit more traditional anyway.

Regardless of what specific decisions they make, they certainly have options, and have the chance to round out an already strong roster with some more quality players this winter. Even with the luxury tax reset as a goal, the Yankees should be plenty active this winter, and will probably enter 2018 as the favorite to win the AL East.