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Acquired LHP Drew Pomeranz from San Diego Padres in exchange for RHP Anderson Espinoza. [7/14]

The Red Sox have a 69.2 percent chance to make the playoffs, and as of 6:00 pm EST last night, their no. 4 starter was an injured Sean O’Sullivan.

That’s why Dave Dombrowski did this, and his ability and willingness to make this deal is why the Red Sox hired Dombrowski. Ben Cherington wouldn’t have made this deal. There’s a pretty good chance Cherington would have been ill at the sight of this deal. But the Red Sox want to and can win now, and to win now you need some semblance of a starting rotation. That’s probably the no. 1 reason why Cherington is gone.

We don’t need to dive too deep to figure out why A.J. Preller did this. The Padres are bad, and he’s found a way to sell Drew Pomeranz at the absolute height of his value. In return, a system that Preller dismantled about 18 months ago gets its new centerpiece in Anderson Espinoza, baseball's no. 24 prospect in BP’s most recent ranking. This is the type of move you dream of making in your dynasty league. Espinoza currently owns a 4.38 ERA in Single-A Greenville, which may have you wondering what all the fuss is about. Said fuss comes from the fact that he’s at such a level at age 18, and that pretty much every scouting report you can find on him indicates that he has a freakish feel for pitching, an explosive fastball, and godly upside.

If only the opinions on Pomeranz were so uniform. The former no. 5 overall pick back in 2010 finds himself in his fifth organization amid what is far and away his best year as a pro. Pomeranz owns a 2.47 ERA, 2.76 DRA, and 28.0 K% so far this season, which helped to earn him an All-Star nod. The 27-year-old walks a few too many batters, but he misses bats, induces ground balls, and is averaging six innings per start. That might sound like “decent starter” to you, but it sounds like “godsend” to those who watch the no. 4 and 5 starters in the Red Sox’s rotation on a weekly basis. Better yet, Pomeranz’s most attractive quality may be that he’s under team control through the 2018 season.

The problems? Pomeranz has already thrown 102 innings, which puts him close to his career high of 147 in 2012. The lanky lefty has the frame to log innings but has had plenty of trouble staying on the mound. That’s part of the reason why the A’s used him primarily out of the bullpen a season ago, and is probably why the Padres only had to part with Yonder Alonso and Mark Rzepczynski to get Pomeranz in their organization last winter. Even more damning, Pomeranz has only truly been good as a starter this season and for a brief stretch in 2014. It’s not unreasonable to assume his breakout at age 27 is real, but it’s not crazy to think he’ll fall back down to earth, either.

Add all these factors together and the general consensus is that Preller has bested Dombrowski for the second time in the past eight months. Since last December, Espinoza, Manuel Margot, Javier Guerra, Carlos Asuaje, and Logan Allen have all made their way to San Diego. Only Craig Kimbrel and Pomeranz have gone east in return. So why do it, then? Why trade a potential Charizard for what may or may not be a Charmeleon right now?

To understand why Dombrowski and Actual GM Mike Hazen (ppl 4get that) would be OK with sacrificing a pitcher with Anderson’s upside for a pitcher with Pomeranz’s imperfections, you have to truly understand the depths of Boston’s failures when it comes to developing, acquiring, and retaining starting pitching. You also have to recognize the dearth of options on both the upcoming free agent and current trade market for quality starting pitching. And finally, you have to remember that making the playoffs is pretty damn hard.

Let’s start with the first point. The Red Sox own the 19th-best ERA in baseball at 4.43. They’ve allowed the ninth-most runs at 424. While their bullpen hasn’t been elite thanks to injuries (Carson Smith, Craig Kimbrel, Junichi Tazawa) and regression (Koji Uehara), the bulk of the blame for their pitching woes falls on the starting rotation, which has posted a 4.74 ERA (though they rank in at 14th according to starter DRA).

David Price has been OK, pitching well below expectations (4.34 ERA) but with underlying stats (3.01 DRA) that suggest he’ll come out of it. Steven Wright has been fantastic, pitching far better than even his biggest fans assumed possible. And Rick Porcello has been a perfectly acceptable mid-rotation asset, keeping his team in the game and doing a better job of keeping the ball in the park.

After those three arms, it gets really, really ugly. Clay Buchholz has gone from providing highs and lows to providing lows and lowers, as his 5.91 ERA suggests. For the first time in his career, he’s been relegated to the bullpen, and he’s a strong candidate to be released as the season progresses. Eduardo Rodriguez was hurt, took a long time to stop being hurt, and was then terrible, allowing 28 earned runs in six starts. So much for the presumptive no. 2 and no. 4 starters when the season began.

The cavalry has been equally uninspiring. Henry Owens got shelled in three starts and has probably walked six batters in Pawtucket since you started reading this paragraph. Joe Kelly gave up nearly a run an inning in his brief stint in the majors. Mercifully, about three years too late, he’s being moved to the bullpen. Brian Johnson has thrown just 33 innings this season as he battles health issues. And Roenis Elias … let us not speak of such things. That’s how you end up with Sean O’Sullivan making four starts for a contender in 2016.

Why do the Red Sox have to resort to options like starting Elias and trading away stud prospects? Because they absolutely, positively, definitively cannot develop starting pitching. Add Owens and maybe Johnson to a list that includes Matt Barnes, Anthony Ranaudo, Allen Webster, Rubby De La Rosa, Brandon Workman, Felix Doubront, Michael Bowden, and so many, many more. Over the past decade, the Red Sox have only successfully developed Jon Lester, Buchholz, and sort of Justin Masterson as rotation stalwarts. It is far and away the organization’s biggest flaw. Maybe Dombrowski thinks he can’t fix that overnight, and that’s why he was willing to deal a potential cornerstone in Espinoza. Or maybe he was willing because he surveyed the market and sees that good starting pitching is going to be mighty hard to come by for a mighty long time.

There are few if any front-of-the-rotation pitchers who figure to be on the market right now. Julio Teheran is one, but he’s going to (rightfully) cost a fortune. One figures Espinoza would be a starting point for him, not the entire return. Sonny Gray is having too strange a year to trade–teams should be leery about buying and the A’s won’t want to sell low. Ditto Chris Archer and the Rays. The Marlins are too good to trade Jose Fernandez. The White Sox too smart to trade Chris Sale. One assumes the Diamondbacks don’t want to trade Zack Greinke and the Phillies don’t want to trade Aaron Nola. The Reds, Brewers, Twins, and Angels and don’t have good pitchers to offer.

That left the Red Sox with a choice. They could settle for back-of-the-rotation fodder like Jeremy Hellickson or Ervin Santana or Bud Norris, gamble on an aging and injured Rich Hill, or take a calculated risk with the one available pitcher who seems to represent a reasonable middle ground in Pomeranz. When you look ahead to next year’s free agent market, you get why Pomeranz’s extra years of control are so important. The names atop next offseason’s FA SP list? Hill, Hellickson, Brett Anderson, Edinson Volquez, Andrew Cashner, and Ivan Nova. And probably Clay Buchholz, of course.

Even if next year’s class was loaded, that wouldn’t help the Red Sox now. And as bad as the back of their starting rotation has been, there’s plenty of reason to believe they can be a real threat with a little help. They’ve scored 490 runs, 30 more than the second-place Cubs. They have incredible young talent up the middle and in Double-A. They have David Ortiz. They should have an effective bullpen if they can keep their arms healthy (quite the if). And with Pomeranz, they have an acceptable top-four in their starting rotation, albeit not one that strikes fear into any hearts.

In the immortal (literally) words of Jon Snow, “battles have been won against greater odds.” This is a team that can make and go deep into the playoffs, and making the playoffs is hard. In adding Pomeranz, Aaron Hill, and Brad Ziegler, Dombrowski has made a run in October much more likely in 2016, and in Pomeranz he’s added a piece that can help beyond this year, too.

That doesn’t mean the Padres have any less cause to feel excitement. They picked an arm up off the scrap heap, fixed him up, and traded him in for $100 lottery ticket. For as poor as some of Preller’s initial moves look in hindsight, this one may be his best stroke yet. The problem is we won’t know how smart it is for several years. And during those formative seasons, while Espinoza is toiling away in the minor leagues, the Red Sox plan to be competing. Dombrowski’s bet is that Pomeranz can stay on the mound enough to help them do so. —Ben Carsley

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Acquired RHP Anderson Espinoza from Boston Red Sox in exchange for LHP Drew Pomeranz. [7/14]

It's hard to believe now, but Espinoza wasn't universally considered the best pitching prospect in the 2014 international class, as many believed his (now former) teammate Christopher Acosta had a higher ceiling. That being said, he was certainly loved, and the Red Sox gave him $1.8 million to procure his services. Since entering the professional ranks, he's seen his stock soar, and he now ranks among the best right-handed pitching prospects in all of baseball.

Espinoza's arm strength is ridiculous. Despite being no taller than six feet and weighing 160 pounds soaking wet, he can get his fastball into the high 90s, and he'll sit comfortably in the 94-96 mph range on most nights. His curveball can make hitters look silly because of its velocity and his ability to locate it with spin, and it flashes plus on a consistent basis. The changeup is another quality offering; one he'll need to use more as he develops but that flashes above average because of his impressive arm speed and some sink. Like most teenagers, Espinoza's command will come and go, but he repeats his delivery extremely well for any age, and he locates better than you typically see a high school senior do.

If there are concerns here, it's two-fold: Is it all too much too soon, and is he going to be able to do this over a full season? Guys who throw this hard this early scare the heck out of people, even when it's not coming from much effort, and calling Espinoza undersized is quite the understatement. That and the automatic volatility that comes from any pitcher–much less a young, small one–makes him not a sure thing, but the upside here competes with any minor-league pitcher in baseball, and you shouldn't be surprised if this is the best pitching prospect come 2018. —Christopher Crawford

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If I thought Pomeranz would match his first half stats in the second half (or even close), I would agree with the Redsox side of this article. That said, he's never brought it for a full season as the article mentions. We don't know how durable he truly will be since he's over 2/3 of the way to his highest IP total already. My main concern however, is that he's a Lefty who gives up more Fly Balls than Groundballs.... heading to Fenway......
"The problems? Pomeranz has already thrown 102 innings, which puts him close to his career high of 147 in 2012. The lanky lefty has the frame to log innings but has had plenty of trouble staying on the mound. That’s part of the reason why the A’s used him primarily out of the bullpen a season ago"
Here's a complete list of pitchers with a better K rate than Pomeranz's 28.0% this year:

1 Jose Fernandez Marlins 12.91 2.60 4.97 0.59 36.6 % 7.4 % 29.2 % .202 1.02 .316 76.6 % 60 53 57 2.52 2.13 0.38 2.35 2.61
2 Clayton Kershaw Dodgers 10.79 0.67 16.11 0.45 32.9 % 2.0 % 30.8 % .184 0.73 .262 79.7 % 45 41 53 1.79 1.70 0.09 2.18 2.31
3 Max Scherzer Nationals 11.56 2.40 4.82 1.48 32.8 % 6.8 % 26.0 % .190 0.96 .241 84.7 % 73 88 78 3.03 3.61 -0.58 3.25 2.97
4 Stephen Strasburg Nationals 11.14 2.62 4.26 0.93 31.4 % 7.4 % 24.1 % .199 1.01 .270 83.5 % 63 72 73 2.62 2.97 -0.35 3.03 3.10
5 Noah Syndergaard Mets 10.90 1.53 7.11 0.51 30.4 % 4.3 % 26.1 % .239 1.08 .337 77.1 % 65 50 59 2.56 2.06 0.50 2.45 2.69
6 Madison Bumgarner Giants 10.13 2.22 4.56 0.83 28.5 % 6.3 % 22.3 % .195 0.96 .255 85.6 % 51 76 82 1.94 2.96 -1.02 3.40 3.30
7 Drew Pomeranz Padres 10.15 3.62 2.80 0.71 28.0 % 10.0 % 18.0 % .182 1.06 .240 80.8 % 63 77 88 2.47 3.18 -0.71 3.66 3.75

The Red Sox did just fine.
I grumbled about this trade at first. My biggest issue is how much risk there is that Pomeranz doesn't provide the help they need in 2016. I feel like I'd want a bit more security if I was trading so much upside in Espinoza, but as Ben pointed out, that kind of pitcher either isn't on the market or would cost one of their top bats plus Espinosa.

I'll reluctantly concede that it was the right move for them to make but still joke that Dombrowski to the Sox was the best thing to happen to San Diego since Tony Gwynn.
Espinoza has grown since initial viewings. He looks more the part than he used to, and will continue to grow and fill out.
"Here's a complete list of pitchers with a better K rate than Pomeranz's 28.0% this year:"
Its been a half year. If someone told you in April that Drew Pomeranz fetched a top 25 prospect, you would have thought that was crazy. 17 starts is not enough sample size to change that. All 6 others have done it before; Pomeranz hasn't. It may be a complete list for the first half, but it is a severely incomplete list of pitchers who are likely to be better than Drew Pomeranz the 2nd half of 2016. I agree that most or all on either list are not currently available for trade. That doesn't mean you need to overpay. If David Price goes from average pitcher to being David Price, that's like acquiring a deadline Ace right there. The Royals have been to the last 2 World Series with worse starting rotations than the Redsox have had so far this year. Granted, they had better bullpens and defense, but the Sox have a much better offense to mitigate some of that.
Here is Baseball Prospectus, the disciples of TINSTAAPP, trying to put some spin on this trade to suggest that the Padres got the best of it. Espinoza, for gosh sakes, is in Low-A, and not exactly setting the league on fire, all be it at 18. I have seen Pomeranz pitch a couple of times this year, on TV, and he has been excellent. A fluke, maybe, and every trade ever made is a crap shoot but this is the kind of bold move that wins World Series.
I've never prescribed to TINSTAAP and I'm not trying to spin a thing.
Agree, that's not how I read it. I read a spin-free presentation of the ups and downs and ins and outs.
Returning to the other Red Sox-Padres trade. The Padres may have received good value for Kimbrel but the Red Sox were packaging excess parts for something that was desperately needed. Margot was not going to play CF in Boston before 2020, if ever, Holt is a much better utility man than Asuaje, Guerra, who is also completely blocked, has been a train wreck in 2016 and Allen is still an unknown. Could the Red Sox have gotten more for this package, I doubt it because the Sox had to have a closer and it had to be now.