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The factors complicating the Yankees’ upcoming negotiations

Masahiro Tanaka and DJ LeMahieu give the Yankees the best shot at winning a ring in the near future. Will the Yankees pay what it takes to retain them?

New York Yankees v Boston Red Sox Photo by Maddie Meyer/Getty Images

Shortly after his final start of the regular season, Masahiro Tanaka uploaded this post to his Instagram, after what he noted was the last regular season start of the seven-year deal he signed with the Yankees. Fellow writer Matt Ferenchick shared the post in the PSA Slack, which caused me to pause and reflect. I was equal parts thankful for the privilege of watching Tanaka pitch for the last seven years, and saddened that opportunities to do so may be drawing to a close. The post also sparked a round table discussion of sorts that I would like to share and dig into.

The Yankees stand to lose four significant contributors from their roster this winter. DJ LeMahieu, Masahiro Tanaka, and James Paxton were all born within 4 months of each other, and are all entering their age-32 seasons. J.A. Happ has been one of the more valuable starters for the Yankees after clunkers in his first two starts, but it appears he will reach neither the starts threshold nor innings limit need for his contract option to vest. There is no denying that subtracting these four players would seriously threaten any chance for the Yankees to contend for a championship next season and beyond.

With that being said, let’s get to the round table which was centered around Tanaka.

Peter Brody: What do you think the Yankees would realistically pay (Tanaka)?

John Griffin: 3/60? 4/80?

Joshua Diemert: 3/65

PB: I was thinking 3/55, 4th year option to 70.

JD: He walks at that price. Gotta get it over $20/year, and at least three years. Maybe a fourth at $15 with a sizable buyout.

From the start, it is nearly impossible to predict how the free agent market will behave this winter. If the last two offseasons have taught us anything, it’s that the marketplace is fickle. Two winters ago there was a relative freeze on spending, with marquee free agents Bryce Harper and Manny Machado signing far later and for less than many expected. Then last winter, owners went on a relative spending bonanza, signing record deal after record deal, notably to guys like Gerrit Cole, Stephen Strasburg, and Anthony Rendon. Throw on top the fact that teams have cited hundreds of millions of dollars in lost revenue due to COVID-19, and projection becomes a fool’s errand.

PB: Keuchel got three years, similar fWAR/year. IDK how the FA market will pan out.

JD: Tanaka’s a full year younger (than Keuchel) and staring at the contract the Yankees gave Happ lol. Well, 11 months younger. Especially if he has a good postseason, someone will put up 60 guaranteed.

PB: Yeah he’s probably the second-best on the market this winter. I think the Yankees might be willing to go four years, and players usually take the highest overall value.

JD: They better, or go way over on AAV but I doubt it.

PB: I’m just worried the Yankees won’t want to pay a starter 20/yr.

JD: Oh I totally get that. But someone will give Tanaka that. And then the Yankees have 3.5 starters.
I think we need to warm up to the idea that Paxton, Tanaka and DJ all get some degree of Cano’d.
Paxton gets Pineada’d: some team takes a chance on a 1+1.
Tanaka gets 3/52 from the Yankees and 3/65 from.....idk the Mets?
DJ gets the full Cano - “Here’s our offer, take it or leave it.”
“Wait where are you going?”
“Oh, St. Louis is giving me like, twenty million dollars more.”
“Yeah but the pinstripes.”

PB: Before they re-sign any pending FAs, the Yankees’ payroll is about $200 MM.

JD: “We were dealing within the financial constraints of the organization, and believe Tyler Wade is ready to step into a starting role.”

This is where the rubber really meets the road. How willing will the Yankees be to exceed the CBT threshold? They spent right up to the third tier this year, and would incur a higher tax doing so for two consecutive seasons. As it stands with committed contracts, arbitration raises, and pre-arbitration salaries, the Yankees will have right around $50 million to spend before breaching the highest tax threshold. That’s more than enough, one would think, to re-sign two of their pending free agents, but having the ability to do something and having the willingness to do something are two separate matters.

The Yankees recent behavior does not inspire a terrible amount of confidence. By that, I am referring to the prior precedent of the Yankees “going with what we’ve got.” At the trade deadline the last two seasons, we’ve heard the same line: getting back healthy players is like making an impact trade. Except that hasn’t entirely worked so far. The Yankees seem to prioritize in-house options over more costly external upgrades, to mixed results.

PB: What does the spectre of a strike do to spending?

JD: Decimate it. Possibly. Idk. Uncharted waters.

JG: Ironically, to some extent I could actually see “the pinstripes” working with Tanaka. For some reason the vibe I have from him is “New York or Japan.”

JD: Yeah maybe. I do think we need to be careful how we talk about that. It’s not far from an honour/loyalty/Japanese dogwhistle stretch.

JG: For sure. My impression comes primarily from his decision not to opt out though.

JD: Sure.

JG: Although it worked out for him (that free agent market sucked).

JD: Although he read the market well. Yeah.

JG: I guess it depends on something we don’t know - how much did the players/their agents know about the slow free agent market before it happened. Like, were they expecting it?

This is the final, yet most elusive, piece of the puzzle. The current CBA expires after next season, which opens a whole new can of worms. What will the payroll limitations look like? Will there be a strike should both sides fail to reach an agreement? These are the uncertainties that could both inflate or depress spending. Some teams may not want to commit long-term money when they don’t know what the future holds, while others may want to push their chips to the middle of the table for next season, as certain championship windows start to close.

At the end of the day, the Yankees need to decide where their priorities lie. If the goal truly is to win a championship, losing Tanaka and LeMahieu could significantly dent the Yankees’ ability to be contenders. DJ is a top-five pure hitter in the AL while Masa is among the top-five all-time in postseason run prevention. They represent the two best available players, either internal or external, to fill their respective roles next season, full stop.

Yet if the goal is to field a winning team that is content with making the postseason, it's not hard to see the Yankees subscribing to the line of thinking that says not to hand out sizable contracts to over-30 players. At the extreme end of the spectrum, LeMahieu could command upwards of Paul Goldschmidt money while Tanaka could be looking at a deal in line with Hyun-Jin Ryu’s pact. Expenditures of that magnitude would surely signal that Yankees ownership is all-in.


Which of their pending free agents should the Yankees re-sign?

This poll is closed

  • 0%
    (14 votes)
  • 20%
    DJ LeMahieu
    (506 votes)
  • 3%
    Masahiro Tanaka
    (73 votes)
  • 0%
    James Paxton
    (6 votes)
  • 65%
    DJ and Masa
    (1587 votes)
  • 2%
    DJ and Pax
    (51 votes)
  • 0%
    Masa and Pax
    (4 votes)
  • 7%
    All three
    (187 votes)
2428 votes total Vote Now