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Trying to Replicate the 2017 Chase Headley Trade: J.A. Happ Edition

As the Yankees were transitioning into a new young core during the 2017-2018 offseason, the Yankees were able to rid themselves of a decently sized contract with trading Chase Headley to the San Diego Padres.

(Side-Note: Covering that deal was one of the first posts I made for SSTN. It’s amazing to see how much has changed in a little under two years.)

In the trade, the Yankees including a pitcher with promise in Bryan Mitchell and received an unproven OF in Jabari Blash. The San Diego Padres obviously had a vested interest in Mitchell and taking on Headley served as a way to get the pitcher without needing to shell out any prospect capital.

This was also after the emergences of other young players Aaron Judge, Gary Sanchez, and Luis Severino- all whom had WAR’s above 4.0 in 2017- and the Yankees had Miguel Andujar in the wings ready to take on the 3B position in 2018.

In this post, we’re going to see if there are any similar deals the Yankees could make following a similar framework to the Chase Headley deal.

Statistically Comparing Chase Headley (2017) to J.A. Happ (2019):

In 2017, Chase Headley hit to a slashline of .273/.352/.406 (.758 OPS) with a perfectly league average OPS+ of 100. He also played in 147 games season between both first and third base. This was his best offensive season that Headley had (he put up +2.6 oWAR) since the 2013 season (where he had a +3.0 oWAR), but his worst defensive season (-0.9 dWAR) since 2009 (-1.7 dWAR).

This defensive dip was probably because he was asked to play a platoon of first and third base after Todd Frazier was acquired before the Trade Deadline, but overall Headley produced +1.9 bWAR in the 2017 season. This was also one year removed from a +2.6 bWAR season in 2016, and back-to-back +3.4 bWAR seasons in 2013 and 2014. Headley was by all means a solid player during his career and the Padres were looking to capitalize on grabbing the final excellence of his career.

Unfortunately for the Padres, Headley only managed to play 60 games for them in 2018, where he hit an abysmal .115/.233/.135 (.368 OPS) with an OPS+ of 7. It didn’t work out for them and Headley was DFA’ed in May of that season.

In 2019, J.A. Happ pitched to a record of 12-8 over 161.1 innings with an ERA of 4.91, a FIP of 5.22, and a WHIP of 1.295. All this combined to a less than league average ERA+ of 90. Happ was however still worth +1.2 bWAR in 2019, which is only slightly below his career average bWAR/season of +1.7.

This dip also came after Happ had put up a fantastic 2018 season totaling +3.3 bWAR for the Toronto Blue Jays and Yankees, and the three following seasons all had bWAR’s above 2.5: +2.6 bWAR in 2015, +4.5 bWAR in 2016, and +3.3 bWAR in 2017. Like Headley, a team that would acquire Happ would be looking to capitalize on trying to get the last excellence of his career.

Obviously, we have no idea how well (or poorly) Happ will perform during the 2020 season, but Baseball Reference has a wonderful projection tool that has J.A. Happ pitching to a 12-8 record with a 4.50 ERA and a WHIP of 1.291 in 158 innings, with a reliability factor for this projection at 77%. This shows that these projections expect Happ to stay consistent, as these numbers match up very well with his statistics from 2019.


The Money Factor and Trade Value:

After looking at the stats, Chase Headley definitely had the better year in 2017 than Happ had in 2019, and going into this next factor (money) would seem to have more trade value. Except, I still think that they would be worth about the same in regards to trade value because of how there is always a bigger demand for average starting pitching than a third-baseman.

When Chase Headley was traded in 2017 he had 1-Year and $13 Million remaining on his contract, to which the Padres completely absorbed. It also wasn’t as if the Padres were swapping salaries as Jabari Blash was still a pre-arbitration player and on a rookie deal.

J.A. Happ on the other-hand still has 1-Year and $17 Million remaining on his guaranteed contract, which could become a total of 2-Years and $34 Million if he reaches 165 innings or 27 starts in 2020 due to a vesting option. It would appear that the more likely factor for Happ in having that option vest would be total starts, as he has started 31 games in both 2018 and 2019.

This vesting option could hurt his trade value because of it being a bigger deal, but I would expect the Yankees to work in a clause with a trade that if the option vests the Yankees will take on some of the salary- similar to how the Miami Marlins had a clause in the Giancarlo Stanton trade about if he doesn’t opt-out after 2020.


Where Could Happ Go?

Following the Chase Headley framework means that in this scenario we can only trade J.A. Happ back to teams that he has previously played for. This includes the Philadelphia Phillies, Houston Astros, Seattle Mariners, Pittsburgh Pirates, and Toronto Blue Jays. (Headley had only ever played for the San Diego Padres outside of his Yankees tenure.)

Luckily, because Happ has moved around a lot, this gives us a fair amount of options (and styles of trade reasoning) to go through. Let’s finally begin:


Team #1: The Philadelphia Phillies

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The Phillies, after agreeing to a 5-Year, $118 Million deal with Zack Wheeler, now have finished creating a 5-Man rotation for 2020 with Aaron Nola, Jake Arrieta, Vince Velazquez, and Zach Eflin. The thing is however, in 2019 both Jake Arrieta (0.9) and Vince Velazquez (0.1) had lower bWAR’s than J.A. Happ. They also haven’t taken themselves out of the current free agent starting pitching market even after getting Zack Wheeler. This is a good thing for the Yankees in trying to work out a trade, considering there is at least a sense of a need.

In trying to think of a deal that may appeal to both sides, the Phillies could also look to improve their bullpen with potentially taking on a player with high upside like Jonathan Loaisiga and/or going with a more healthy piece in Luis Cessa. (Both players have positive trade values on

Returning to the Yankees could be somebody like catcher Andrew Knapp, who could potentially fix the Yankees plans are back-up catcher.

You also have to remember that this deal would open up 2 spots on the Yankees 40-Man roster, which could very well go to some free agent signings (think: Cole, Garnder, Betances to name a few).


Team #2: The Houston Astros

The Astros are going to be losing Gerrit Cole this offseason. However, according to their official MLB depth chart they still have 7 prospective starting pitchers for 2020 in their current rotation. They also haven’t been involved in many rumors surrounding the starting pitching free agent market, which would mean that they probably aren’t interested in making any big changes from what they have.

Plus, this is a team with very little holes as to where a deal could work to add a piece for the price of Happ’s contract. If anything, a deal would be very similar to the Phillies as they would look to prioritize relief pitching help.

All that being said however, a trade between the Astros and Yankees is almost guaranteed to not happen, most likely because of the recent cheating allegations that the Yankees had against them too.



Team #3: The Seattle Mariners

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The Mariners going into 2020 are most likely not looking to seriously compete, but otherwise acquire talent for the future. They are also a team that could use a veteran innings-eater like J.A. Happ in their rotation, especially considering that only one of their pitchers to start 5 or more games for them in 2019 had an ERA under 4.00 (which was Marco Gonzalez at 3.99). Happ would be one of their better rotational arms and would allow them to acquire some minor league talent.

The fit seems to work, as they could to go after a combination of Michael King-who I understand is highly regarded- and Nick Nelson (Yankees #14 Prospect), both of whom could potentially become pieces of their rotation or bullpen in the future.

Returning to the Yankees could be OF Keon Broxton as a 1st-year arbitration piece who won’t be looking to make much (he’s has a career -0.8 bWAR) and could slot in as a utility outfielder.

There’s some potential here.


Team Four: The Pittsburgh Pirates

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The Pirates would find themselves to be another team that would be using a trade for J.A. Happ to acquire future talent. However, their starting pitching looks to be even worse than the Mariners, as only 1 pitcher who started a single game had an ERA under 4.00, being relief pitcher Michael Feliz. All other pitchers who started even a single game had an ERA over 4.00, with all but 3 of them going over 5.00! Not good.

This deal would most likely look similar in nature to the Mariners deal above except adding in further away talent from the Yankees like T.J. Sikkema (Yankees #16 Prospect) and/or Osiel Rodriguez (Yankees #28 Prospect). Potentially, this could bring back a player maybe Nick Burdi, coming to the Yankees. (I am biased in that pick, as a college friend of mine knows the Burdi brothers and I think it’d be cool if they were Yankees.)

For whatever reason, I just don’t see the Pirates making a trade with the Yankees for J.A. Happ, but this would be cool to see.


Team #5: The Toronto Blue Jays

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An inter-division trade with a team that has lots of young prospects and major league talent in, of whom could be a surprise team in 2020 would be interesting. However, like both the Mariners and Pirates, they very much lack veteran starting pitching, and would probably look to get more major league level help in a deal as their window to compete is close.

For them, I decided on sending both Jonathan Loaisiga and Stephen Tarpley. Both MLB-ready (or close to) talent who have decent ceilings, for Elvis Luciano. I was trying not to use the same players over-and-over, but I couldn’t find a deal that looked good enough without adding Loaisiga. I also think that getting Luciano would be kinda cool because he is only 19 and was seen by at least one major league franchise as MLB-ready.



This was an interesting exercise to try and work my way through. I do think that J.A. Happ will be in a new uniform next year- especially if the Yankees end up getting a top-tier pitcher whose name is what children typically don’t want in their Christmas stockings- and very much think that he could be going to the Phillies.

For whatever reason, I could see him being their alternative because they also missed out on bringing back another veteran arm in Cole Hamels, who signed with the Braves.

Regardless, I’m hoping for lots of speculation, rumors, and trades occurring over this next week in baseball as the Winter Meetings begin!

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Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


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