The VF314 Official 2019-2020 Offseason Plan

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With the Nationals crowned champions and MLB’s offseason underway, it’s time for us to unveil our Official Offseason Plan for the Yankees. Everyone on staff has discussed and debated various decisions the Yankees have ahead of them this winter and are ready to share our consensus today.

As a preface, this plan is an attempt at what we believe is realistic for the Yankees over the coming months. We’re increasing payroll, but remaining in the same luxury tax tier that the team was in for the 2019 campaign. That led to some difficult decisions that you’ll see unfold below.

With that, let’s dive right in.

Option decisions

Aroldis Chapman: Pretty simple here: Chapman’s arm is a luxury that Yankees cannot afford in this plan, so the team would just let him opt-out and leave. The Yanks would reap a fourth-round pick as compensation by offering the qualifying offer, which he’d presumably decline. They can find lower-priced relievers and spread the $$$ elsewhere. They would, however, have a small luxury tax penalty since his contract was frontloaded.

In reality, the Yankees are more likely to extend him, but that would create hard choices and leave them with little flexibility this offseason or in upgrading elsewhere.

Edwin Encarnación: The real life Yankees declined his $20 million option for 2020. That’s what we planned to do too.

Team Free Agents & Qualifying Offers

Staying put: Brett Gardner and Dellin Betances

Gardy stays on a one year, $7.5 million deal. It’s a redux of his contract from the 2019 season. He’ll open the year as the starting center fielder as the Yankees wait for Aaron Hicks to return from Tommy John surgery.

Dellin returns on a one year, $2 million contract plus potential for $5 million in incentives. Additionally, a 2021 club option worth $12 million or $1 million to decline. After a heartbreaking 2019, we want to give Dellin a chance to make it back with a decent base salary along with plenty of incentives.

Departing: Didi Gregorius, Austin Romine, Cameron Maybin, and Cory Gearrin

This was painful. Letting Didi go means you’re losing part of your soul, a key leader on the roster. Romine has been a strong backup catcher and should remain one, but we couldn’t fit him under the top CBT threshold. If the Yankees don’t get Cole, their returns become more realistic. We’re also not planning to offer a qualifying offer to Didi here.

Free Agency

Sign Gerrit cole to an 8-year, $240 million deal. This is the centerpiece of the Views from 314ft plan. In this world, you engage Cole early, endulge Scott Boras’ nautical themed public comments and give the former Astros right-hander the most money ever to a free agent pitcher. The deal includes an opt-out after the fourth year and is backloaded.

We chose to give Cole an eighth year in the deal both because negotiations might go there anyway, and it also buys you more room under the luxury tax. He’s the best starter available and he fits the Yankees’ needs to a tee. There are hard choices that the team has to make to fit him under the top luxury tax threshold, but those are choices worth making.

Right away, Cole would slot into the top spot in the rotation ahead of Luis Severino, James Paxton, and Masahiro Tanaka in one of the more formidable AL rotations. With their strong bullpen, the Yankees can lay off Cole early in the season if he’s fatigued by a long playoff run and thus gear him for October 2020 in the Bronx.

Sign Drew Pomeranz for one year and $4.5 million with a $6 million 2021 club option or $500k buyout. Pomeranz failed as a starter in San Francisco last year, but he was dominant as a reliever in his brief stay with the Brewers after the trade deadline. He cut back on his curveball usage and became a two-pitch reliever, pumping his high-spin fastball into the mid-to-upper 90s while still mixing in the curve. He became a completely different pitcher.

Over 26 1/3 innings with Milwaukee, Pomeranz held opponents to just 16 hits, eight walks and seven runs while striking out 45. He boasted an insane 45 percent strikeout rate during that stint.

With the Yankees, Pomeranz could be another back-end reliever to replace Chapman, though he’d pitch closer to the middle innings. With his background as a starter, there’s some multi-inning potential, though he throws much harder now. If he prices the Yanks out, then they can retain Luis Cessa instead of trading him as we do below. A second-year guarantee would make sense if the bidding requires it.

Sign Eric Thames to a one year contract worth $5 million. We’re banking on the Brewers declining Thames’s $7.5 million option. They have sixteen players eligible for arbitration this year and generally don’t spend much in the first place, so they’ll need to cut costs somewhere.

He can play first, DH and even fake it in the outfield corners. Best of all, he brings left-handed power to a team sorely lacking that. Thames hit 25 bombs in 459 plate appearances last season.


We know, we know, but we can’t help ourselves. To aid in reasonableness, we used Baseball Trade Values to evaluate our ideas. Off we go:

JA Happ, Albert Abreu, and $6 million to the White Sox for Adam Engel. For the rest of our plan to fall into place, we need to unload some of Happ’s $17 million luxury tax payroll hit. To do so, we’re attaching Albert Abreu and $6 million to the White Sox in exchange for centerfielder Adam Engel. We like Engel for his defense, speed and option remaining so he can serve as an up-and-down outfielder in 2020.

Clint Frazier, Nick Nelson, and Ryder Green to the Rockies for Jon Gray. With Happ departing, the Yankees need another starter instead of relying upon Jonathan Loaisiga, Jordan Montgomery, and Domingo German, who currently doesn’t count towards the 40-man roster while on the restricted list.

Gray rebounded from a dud in 2018 to again be the Rockies’ best starter in 2019. His control and injury history leave something to be desired, but he’s been well-above league average considering he calls Coors Field home. The Yankees have liked him for a while, drafting him in the 10th round in 2011.

Meanwhile, Frazier has been seen as trade bait for the better part of two years and we figured his time in New York is coming to a close. Nelson gives Colorado a fine starting prospect in Double-A, while Green is a high-upside outfielder in the low Minors. He was the Yankees’ 3rd-round selection in 2018.

Chance Adams, Miguel Yajure, and Isiah Gilliam to the Pirates for Richard Rodriguez. Rodriguez caught our eye because of his peculiar pitch usage. He throws his fastball more than 80 percent of the time even though his slider gets much more movement than average, per Statcast. It also generates a high number of whiffs. He had a really good season for Pittsburgh in 2018, but took a step back last year. Adams gives the Pirates a potential big league arm for 2020 if he can figure things out while clearing some 40-man roster space for the Yankees. Yajure is Rule 5 eligible, but we don’t have room for him though the Pirates likely do. Gilliam is a low-level prospect with upside but lukewarm performance to date.

Greg Bird to the Tigers for international bonus pool slot money or a low-level prospect. Bird needs a change of scenery and a fresh start, both of which Detroit can offer. He’s projected to earn $1.3 million in arbitration, which we don’t want to carry given Luke Voit and Mike Ford already on the 40-man roster along with luxury tax implications. Ideally, Detroit would send back some IFA money or a low-level prospect (Sam McMillan a catcher with a 35+ FV per Fangraphs, perhaps). Worst case scenario: Bird gets non-tendered.

Luis Cessa to the Angels for minor league right-hander Aaron Hernandez. We didn’t want to trade Cessa, who is a quality long man, but his modest salary and 40-man spot made it hard to keep him. In exchange, the Yankees can dote on a High-A starter in Hernandez. The 2018 draft pick will likely end up a reliever in the long run.

Rule 5 Protection

We created room to add five players to the Yankees’ 40-man roster and protect them from the Rule 5 draft: Deivi García, Luis Gil, Luis Medina, Estevan Florial, and Kyle Holder. García, Gil and Medina are three of the top five pitchers in the Yankees’ system and are easy decisions to keep.

Despite stalling in part due to injuries last season, Estevan Florial still has strong upside as a good-hitting, elite-fielding outfielder. He needs to be protected.

Holder, meanwhile, is the type of player that can be snatched up easily with the implementation of 26-man rosters. The slick-fielding shortstop held his own (119 wRC+) at the plate in Double-A last year and gave highlight-reel plays on a nightly basis. A second-division team can hold him on their bench, and he has upside as a potential utility man in the Bronx.

We, unfortunately, left off Miguel Yajure, Nick Nelson, and Chris Gittens, among others. Therefore, Yajure and Nelson became expendable in the trades above. Yajure might have higher upside yet has few innings due to Tommy John surgery. Gittens is squeezed out in the Bronx as a 25-year-old 1B/DH even as the 2018 Eastern League MVP.


Non-tender Tyler Lyons and Jake Barrett. With our plan the Yankees are going to add plenty of pitching and these are the low guys in the pecking order. Lyons is a LOOGY in a league that just outlawed LOOGYS starting in 2020. Barrett is coming off an injury and was at the back of the 40-man roster to begin with.

DFA Nestor Cortes and Stephen Tarpley. Meanwhile, the Yankees can look to get something for Cortes and Tarpley. Cortes is more likely to slip through waivers and get outrighted, while Tarpley has enough upside to be traded for a low-level return. He could become a good reliever with health and his bowling ball sinker, but the Yankees have enough other options.

40-Man Roster & Luxury Tax Payroll

  • Guaranteed contracts (13, $173.5M): Gerrit Cole, Giancarlo Stanton, Masahiro Tanaka, Jacoby Ellsbury, Zack Britton, DJ LeMahieu, Aaron Hicks, Luis Severino, Adam Ottavino, Brett Gardner, Eric Thames, Drew Pomeranz, Dellin Betances
  • Arbitration Eligible (9, $39.1M*): James Paxton, Aaron Judge, Gary Sánchez, Jon Gray, Tommy Kahnle, Gio Urshela, Chad Green, Jordan Montgomery, Jonathan Holder
  • Pre-Arbitration (19, $6.25M*): Miguel Andújar, Gleyber Torres, Luke Voit, Mike Tauchman, Kyle Higashioka, Tyler Wade, Jonathan Loaisiga, Richard Rodriguez, Domingo German, Ben Heller, Thairo Estrada, Mike Ford, Adam Engel, Mike King, Deivi García, Luis Gil, Luis Medina, Estevan Florial, Kyle Holder
  • Other ($27.4M)
    • Player benefits: $15 million (estimate)
    • Incentives – Dellin Betances: up to $5 million, assume maximum.
    • Opt out adjustment – Aroldis Chapman: $4.4 million
    • Cash to Detroit: $6 million
    • Cash from Miami: ($3 million)

TOTAL: $246.25M

*We’ve allocated $4 million for pre-arbitration players on the Major League roster and $2.25M for pay to 40-man players while in the minor leagues. Note that some of the arbitration eligible players could spend some time in the minors next season, which would be on a lower salary than their final arbitration figure (a split-contract). Additionally, we used MLB Trade Rumors’ arbitration projections for this plan.

If you counted, there are indeed 41 players listed above. However, as mentioned before, Domingo Germán does not count while on the restricted list during MLB’s investigation into his domestic violence allegation.

The total Competitive Balance Tax payroll shown is $246.25 million, but could be as low as $241.25 million depending on incentives. This is below the highest tax threshold of $248 million. The payroll is also higher than the $234 million amount that Cot’s estimated for 2019.

Transaction Summary


  • Gerrit Cole
  • Dellin Betances
  • Brett Gardner
  • Jon Gray
  • Adam Engel
  • Drew Pomeranz
  • Richard Rodriguez
  • Eric Thames
  • Deivi Garcia
  • Luis Gil
  • Luis Medina
  • Estevan Florial
  • Kyle Holder


  • Aroldis Chapman
  • Edwin Encarnación
  • Didi Gregorius
  • Austin Romine
  • Cory Gearrin
  • Tyler Lyons
  • Jake Barrett
  • Greg Bird
  • JA Happ
  • Albert Abreu
  • Clint Frazier
  • Chance Adams
  • Nestor Cortes
  • Luis Cessa
  • Stephen Tarpley


Mailbag: Player Evaluation, Chapman, DJLM Extension, The Miller Trade Revisited, Yu Darvish Trade


News & Notes: Pitching Coach Search, Chapman, John Sterling, Japanese Star, Domingo Acevedo, Merchandise Dispute


  1. dan

    Good work, but I think the Betances and Pomeranz estimates are way too low

  2. Yanks317

    I’d be surprised if Dellin had to settle for that deal. But I’d be completely fine if they just guaranteed the $8m and made the $12m option a vesting one based on some of those incentives.

  3. Interesting plan. Some comments:
    1. I doubt $240M will be enough to get Cole. This is going to be the biggest contract given to a SP. $280M seems more likely.
    2. I doubt Colorado would make that trade. What about trading Frazier, Voit and Happ for Gray, straight up (no money)?
    3. Why would the rebuilding Chisox trade their starting CF for an old, expensive SP and a prospect that’s not close to the majors?
    4. Love Eric Thames, but we have a glut of 1B and we need to save money.
    5. Keep Cessa. He’s cheap and was really good for most of 2019.
    6. I’d rather have Didi than Voit or Thames in the infield (along with Torres, Urshela and LeMahieu). Didi is left-handed, a fan favorite and clutch in the postseason. Give Didi a 5-year contract worth $40-$50M. We can afford it by (1) not getting Thames, (2) not paying for part of Happ’s salary (if we include Voit and Frazier with Happ, maybe some team will bite), and (3) if necessary, not getting Pomeranz. We lose Chappy but Dellin and Holder will be back, plus Deivi and Mike King.

    • Yanks317

      The previous largest contract to a pitcher is $217m, baseballs economics are broken. If he sets the bar at $280m I’d be shocked. Not saying I think it’s unreasonable, just saying I don’t think the teams will let the bidding get that high.

  4. Wire Fan

    The LT # in this plan is probably too close to the final threshold for comfort. It doesn’t leave much room for DL trips (even league min call-ups start adding up) and means any in season deal essentially has to be LT neutral.

    Is Thames necessary with a league min Ford? Not only would that save some extra LT space but it would also free up a 40 man spot (maybe you don’t DFA Tarpley or hang on to Yajure?). The 26 man also becomes a bit messy with Voit, Thames and Andujar all on the roster especially if the Yankees have Stanton and Sanchez grabbing DH ABs.

    I like the idea of signing Pomeranz if you let Chapman walk, especially if he comes that cheap. I suspect he will get a 2 year deal at maybe a higher AAV though.

    Leaving the BUC duties to Higgy is a bit risky given his injury history, as well as Gary’s. If they go that route they need a decent journeyman C stashed in AAA.

  5. Chris

    Think you have to give Didi a qualifying offer and see what happens. Just think he’s too good not to both on and off the field.

    • Yanks317

      The 4th round pick is not nearly worth the chance he accepts and blows up your offseason plan at 17.6m. DJLM got 12m per year last offseason, Didi should get a similar pact, maybe an additional year.

  6. RetroRob

    I still don’t understand the Chapman adjustment. I don’t doubt it, but I’ve never heard of it if the player opts out. Does the full amount hit against the 2019 payroll for luxury tax purposes? 2020? Or are past years recalculated based on the tax rates of those seasons?

    I do think Cole will get 8 years. I also think he may score upwards of $280 million. Boras will want to set a new record for pitchers both in total value and AAV. Of course, what Scott wants he doesn’t always necessarily get, but he may here.

    If the Yankees do decide to go in big on Cole, they may opt to go through the second luxury tax tier for a year knowing that both Ellsbury and Tanaka are coming off the books after 2020.

    Fun write up. I haven’t looked closely at those trades yet!

    • Derek

      It’s confusing, but it hits the 2020 calc. Basically, since Chapman is opting out of 2 years and $30 million, that changes his original contract to 3 years and $56 million (18.67M AAV) instead of 5 years $86 million (17.2 AAV). So in one fell swoop, the 2020 CBT total adds back the three prior years that were undercomputed for lack of a better word.

      Thanks for reading!

      • RetroRob

        Interesting. So that also means Chapman, without negotiating a new contract, would immediately own the highest AAV for any relief pitcher, eclipsing Wade Davis’ prior record simply by opting out. I really have no idea what’s going to happen here. Part of me thinks they will negotiate an extension, while another part of me equally believes the Yankees will do what they did with Tanaka and won’t budge. I believe we’ll know by noon on Saturday.

  7. Ben

    Should you include the Encarnacion buy-out above?

    • Derek

      The buyout is already computed in his AAV from his original contract since it was guaranteed money, meaning that it counted against 2019’s payroll.

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