The Yankees could sign Aaron Judge and Gary Sanchez to team-friendly extensions

After it became clear that the Yankees were not signing Manny Machado or Bryce Harper, I wrote a post questioning whether the Yankees were actually going to extend their young stars. I didn’t buy the reasoning that the Yankees passed on handing out big contracts in free agency in order to pave way for extensions, because I assumed that their young stars - Aaron Judge, Gary Sanchez, and Luis Severino - would command high AAVs and long-term commitments. Those types of deals are precisely what the Yankees’ brass seems averse to right now. I didn’t reach a clear conclusion, but I did voice my skepticism about the Yankees actually extending all, or most, of their current core.

Because the universe likes to make me look stupid, the Yankees went on to sign both Luis Severino and Aaron Hicks to extensions in the following weeks. What’s more, they were both signed to far fewer years and/or total dollar value than I initially expected. Severino’s new contract came in at four years and $40 million (plus a one-year club option for $12.25 million), while Hicks’ deal was much longer at seven years, but essentially the same in terms of AAV. The Yankees signed two of their core players to extremely team-friendly contracts, answering many of their future roster questions.

In light of these developments, it seems I underestimated the possibility of the Yankees securing extensions with Judge and Sanchez. Both could very well stay Yankees for the foreseeable future, and not because the Yankees are willing to pony up serious money for top-tier talent. The current state of the free agent market, along with the warts in Judge and Sanchez’s profile, may allow the Yankees to tie them down for cheaper and/or on shorter terms. That’s exactly what they did with Hicks and Severino.

Now, I’m not arguing that Judge and Sanchez’s extensions will be the same price and length as Hicks’ or Severino’s. In Judge’s case, he’s clearly a tier above Hicks and slightly above Severino in terms of production. Even with recent trends, I have no problem with declaring that the big man will command more dollars per annum than either player.

Sanchez will come cheaper than Judge, but still will likely cost more than Hicks and Severino. He may not be as productive or consistent as Judge, but given the extremely weak catching landscape in MLB at the moment, Gary is still a top-three catcher even when you include his horrid 2018. That is an extremely valuable asset to have, and it will likely cost more than $10 million per year.

Yet, both Judge and Sanchez have flaws in their profiles. The front office will probably exploit them during contract negotiations to drive down the price and length of their prospective deals. The free agent market for position players is extremely punishing for those who aren’t 26 years old with 30 WAR careers under their belts. One can see why Judge and Sanchez might agree to terms previously unthinkable.

In Judge’s case, he will be in his late-20s when he enters his arbitration years, and 30 when he hits free agency, putting a damper on his leverage. The Yankees could approach him with a shorter-term, high AAV deal to buy out his arbitration years and maybe one or two years of free agency. That’s when he will likely still be productive, and avoid his mid-to late thirties. Conversely, they might approach Judge with a long-term deal with relative low AAV; this way Judge gets job security throughout his thirties, while the Yankees get ridiculous surplus value early on and mitigate their losses at the end of the contract. Either way, Judge’s extension probably won’t resemble Nolan Arenado’s mega-deal signed earlier this winter.

Sanchez’s flaws are even easier to exploit. His subpar 2018 will be a black mark on his resume, inviting questions about his offensive consistency and floor. Defensively, Sanchez’s lack of blocking skills clouds his future behind the plate, and if he’s not catching, he’s not nearly as valuable. Depending on how the next few years play out, the Yankees may actually be able to sign him for something like $80 million over five years, cheaper than what they paid for Brian McCann in the 2013-2014 offseason.

There’s nothing new about players’ weaknesses being used to drive down their prices. That’s just part of contract negotiations. What is different about the recent landscape is that players seemingly have less negotiating power than they did before. It used to be that teams had to take on risk and pay up to get desired talent, whether that be in extension negotiations or free agent signings. Now, it seems like players are increasingly accommodating of the terms offered to them by their teams, however club-friendly they may be.

Make no mistake, this development is a massive boon for the Yankees. Where retaining their core used to seem too expensive, the Severino and Hicks deals make the prospect of both Judge and Sanchez remaining Yankees long-term a distinct possibility. Until changes are made to the way young players are compensated in MLB — which seems unlikely to happen anytime soon — this will likely be the Yankees’ modus operandi: acquire prospects, develop them, and extend them on the cheap.