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Point/Counterpoint – The Jameson Taillon Trade

By Andy Singer and Mike Whiteman

Photo Credit: Mike Carlson, Getty Images

Photo Credit: Mike Carlson, Getty Images

Following this weekend’s blockbuster trade that sent Jameson Taillon from the Pirates to the Yankees in exchange for Miguel Yajure, Roansy Contreras, Canaan Smith, and Maikol Escotto, SSTN’s Andy Singer and Mike Whiteman got together to discuss the deal and its impact on the Yankees. Andy and Mike discussed the trade through the prism of 6 general topics and questions. Below is the transcript of their discussion:

Does Jameson Taillon make sense for the Yankees? How does he fit into the Yankee rotation both now and in the future?

Mike: Taillon’s definitely a talented pitcher; and it always makes sense to acquire talented pitchers. Get as many as you can! Of course, we know he’s a talented pitcher who had his second Tommy John surgery in 2019. The outlook for pitchers having second TJ surgery is historically not as encouraging as those undergoing the procedure for the first time.

That being said, many of those having it done a second time were in their 30s and already in the decline phase of their career. Tallion is 29, which will hopefully be to his favor. Perhaps the best known successful pitcher coming off a second TJ surgery is old friend Nathan Eovaldi, who at age 28 recovered and was impact pitcher for the 2018 World Series Champion Red Sox.

Taillon adds another question mark to the Yankee rotation. It’s a bit scary thinking about the Yankee rotation hopefuls Brian Cashman and Aaron Boone are banking for a return to health in 2021 (Kluber, Severino, Taillon), return from suspension (German) or doing it for the first time (Schmidt, Garcia, King). Jordan Montgomery has thrown all of 75 innings since 2018, and of the rotation possibilities outside of Gerrit Cole, I have the least concern for him.


Andy: The Eovaldi comparison is really interesting to consider, and hey, Eovaldi was a key piece on a World Series pitching staff, so I’m all in if that’s the outcome. In truth, Taillon was a better pitcher than Eovaldi was prior to his 2nd Tommy John Surgery, so if the stuff is close to what it was before, I really like where Taillon slots in for the Yankees.

I think there’s good reason to be optimistic on Taillon’s outlook. Taillon has come back from significant adversity numerous times throughout his career, and he was in the midst of a breakout when his elbow gave way again in 2019, having posted 4.9 bWAR in 2018 (and 8.8 bWAR between 2016 and 2019). Additionally, Taillon’s pitch quality and stuff was nearly elite when we last saw him pitch: 77th percentile fastball velocity, 62nd percentile fastball spin, and 82nd percentile curve spin. I would argue that Taillon even has some upside compared to what we last saw: Taillon still threw a sinker 19-22% of the time from 2018-2019 (typical for Pirates pitchers, who are taught to lean on the 2-seam fastball), which could have suppressed his strikeout numbers. Gerrit Cole made a similar adjustment when he arrived in Houston from Pittsburgh, and his career took off when he adjusted his repertoire to suit his stuff. If Taillon comes back from TJS with stuff that approaches what we saw in 2018-2019, then I’d be all-in on betting that the Yankees could help him lean on his 4-seamer up in the zone, and mix the slider, curve, and change-up to maximize his talent.

Even if Taillon is moderately successful in his comeback, he slots into the heart of the Yankee rotation for the next 2 seasons. I agree with you that in a risky rotation, it feels strange to be worried the least about Jordan Montgomery, but I still love Taillon’s fit given the likely range of outcomes here.

How did the Yankees do with this trade – did they give up too much value, get a steal, or is this about right?

Andy: There are a lot of journalists that have chosen to classify the Pirates’ return in this deal as quantity over quality, but I really think that is an oversimplification. No, Pittsburgh hasn’t skimmed the cream of the Yankee prospect crop in this deal, but that is more a function of how deep the Yankees’ farm system remains even today following this deal. Pittsburgh should be quite pleased with the return for two years of Jameson Taillon. I fully expect Yajure, Contreras, Smith, and Escotto to rank higher in Pittsburgh’s system than they did in the Yankees’ system. Pittsburgh is a team at the beginning of a massive rebuild, and they acquired multiple good prospects.

Taillon, as you note, is trying to do what few pitchers have done successfully in coming back from 2 Tommy John Surgeries, so he is a very real risk for the Yankees. That said, Taillon remains an immensely talented risk, and despite the injury, workload, and mechanical concerns, teams will always have to pay for talented pitching.

Realistically, I think this is a fair trade for both sides. Pittsburgh gets to continue their rebuild with a solid group of prospects of varying stages of development while the Yankees get to dream of a potential #2 to pair with Gerrit Cole.


Mike: I also think it’s a fair deal, perhaps with a small tilt towards the Pirates. Our colleague Ethan Semendinger broke down the trade really well in his article Sunday:

I can reasonably see Yajure, Contreras, Smith on a big league roster someday and Escotto is the desirable “lottery ticket” we see in deals, and a pretty good one. You are spot on about Pittsburgh being in total rebuild, and they have added some nice pieces to the system.

I don’t think that the overpay was egregious, and it’s a risk worth taking for Cashman. The Yankees are playing for now, and none of the players dealt would be significant Yankee contributors in 2021.

Is there a headlining prospect in this trade? Will the Yankees miss one of these guys down the road?

Mike: Yajure (#14 2020 SSTN prospect list) Contreras (#19 SSTN), Smith (#21 SSTN) all have had success in the lower minors, and Escotto has good looking power for an eighteen year old. We’ll likely see Yajure first in the majors, but losing Smith was a bit disappointing to me, as he already has a pretty mature approach to hitting.


Andy: Actually, when we did our own internal rankings last Spring in the SSTN Top-15 Prospects series, we were all pretty high on Yajure, who ended up at #4 on our crowdsourced list. Yajure made us look pretty good in 2020, as he held up well in limited innings despite needing more seasoning in the minors. I think Yajure has a pretty safe floor as a back-end starter, but with the velocity he’s added between 2019 and 2020, I think there is hope that he could be better than that given that he already has control and command over 3 solid pitches. He’ll likely throw significant innings for the Pirates as soon as this year.

As you note though, this is a pretty solid collection of guys. Contreras is also a relatively safe back-end rotation piece; Smith is a large-bodied outfielder with some speed who has posted some really good numbers in age-appropriate levels with good exit velocity numbers; and Escotto is the lottery pick you can dream on, given the probability that he’ll say on the infield dirt and his pop at a young age. The Yankee system is so deep that these prospects won’t be missed terribly, but it’s a great haul for a rebuilding Pirates team. I may be in the minority on this one, but I really don’t think that this was an overpay. 2 years of team control (or two years of cheap control, in other words) for a super talented, but risky starter due to injuries, rehabilitation, and mechanical changes should still be expensive. I think this was an even trade.

How good is the Yankee rotation now? Is this a World Series caliber rotation?

Andy: Stop me if you’ve heard the phrase, “If everything breaks right…” in reference to the Yankees, but…if everything breaks right, yes, this is a World Series caliber rotation. In fact, I would go as far as saying that the Yankees have a top-3 rotation in all of baseball if everyone hits their reasonable 95th percentile projection. That said, I understand a lot has to go right. This is a risky rotation to project, but I think that given what was available this offseason, the choices Brian Cashman has made gives the Yankees as good a chance to have a championship caliber rotation as any moves he could have made.

Even if one or two guys from the group of Kluber, Taillon, and Severino don’t come back all the way, I still remain optimistic that Monty will be a steady arm in the back of the rotation, and it would only take one of Garcia or Schmidt to break out as a 2+ WAR pitcher to make the rotation formidable in the postseason. While the rotation is risky, there are now multiple paths to having a rotation that is greatly improved from the one that was severely undermanned in 2020. Added depth makes me feel a lot better about this rotation.


Mike: “If things break right”, this could be a scary rotation. How about Cole, Kluber, Severino and Taillon at the 95th percentile projection?

We obviously can’t count on that, as TJ surgery recovery is often a bumpy journey, with time needed to recover full strength and command, and that full recovery doesn’t just come from throwing programs and bullpen workouts. The kinks are worked out in game situations. I think there will be early challenges, and they will utilize all of their depth.

I think Montgomery may be the key to 2021. The Yanks really need a second starter to “ride” aside from Cole. You don’t plan to ride pitchers coming back from injury or young hurlers who haven’t put in significant work at the MLB level. A reliable Monty takes a lot of pressure off the whole staff. The ironic thing is that while I think the big lefty is crucial to the team’s fortunes, he may not even be in line for a postseason start if everything breaks the right way.

Would you have made this move if you were Brian Cashman? Given the assumed budget with which Cashman is working under, would you have acted differently?

Mike: Given the Yankees’ self-imposed budget, I think this was a creative move by Cashman. Taillon’s $2.25 million salary fits in well, and there is significant upside if healthy. If they can get 2018 Eovaldi-like performance from Taillon in 2021, he would be a bargain.

As noted earlier, the Yanks didn’t touch their top ten prospects in making this deal (though Yajure may have approached it if reassessed in the Spring), so there’s plenty of players left for another deal this offseason, or more likely during the season.

A possible X factor in this deal is Taillon’s rehab work, which has included mechanical adjustments which he hopes to improve performance and durability at the same time.


Andy: Your point regarding Taillon’s mechanical adjustments is a really good one, and that’s the key here. Taillon was known for having very long arm action through the early part of his delivery, and there is video evidence that shows that he is working on shortening that action up significantly. The upshot is that long arm action makes pitchers more prone to elbow injuries, and changing this action should help Taillon’s durability in the long run without hurting Taillon’s stuff. For me, the key is ensuring that Taillon maintains his devastating ability to spin a breaking ball, which is one of the toughest transitions when shortening arm action (sadly, I know from experience on that one).

To answer the question though, I make this trade every day of the week if I’m Brian Cashman, even taking into account that I’m higher on Yajure than most prospect observers and evaluators. The $210 million luxury tax threshold seems to be a hard budget cap for the Yankees this offseason. Whether I like it or not, given the reality of the situation, trades like this make a ton of sense for the Yankees. Brian Cashman has done a lot with a little to shore up the Yankees’ most glaring weakness last season.

Are the Yankees done making big moves this offseason?

Andy: It depends on the definition of “big.” I had said last week that I expected Ottavino to get traded in a salary dump, and that happened on Monday. Given that move, my rough math indicates that the Yankees have roughly $10.5 million remaining under the first luxury tax threshold of $210 million. With that money, I fully expect Brett Gardner to return on a small, one-year deal, and I also think that the Yanks can go out and get a reliever with question marks (maybe someone like Trevor Rosenthal). Besides that, I think the bulk of the offseason work is done at this point.


Mike: I think you’re right about signing Gardner, and then I think Cashman will wait for a bargain to come his way right before or after the start of Spring Training. There are plenty of capable bullpen arms still out there.

Now, if Masahiro Takana’s price were to drop under $10 million, though highly unlikely, I wouldn’t put it past Cashman to pounce. I’ve read that Tanaka would go back to Japan before he plays here in the US for that low of a salary. Stranger things have happened before. I still remember when Andy Pettite so wanted to come back to the Yanks from retirement in 2012 that he settled for a $2.5 million contract.

In all likelihood though, I agree that the 2021 Yankees team is just about complete.


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