Red Sox: A return look at four key deals. How is it working out?

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BOSTON, MA – SEPTEMBER 18: Dave Dombrowski (Photo by Rich Gagnon/Getty Images) /

Just what are the best trades in baseball? For far too many fans the best means you have “won” the deal when your player(s) acquired outperform those that you traded or have been instrumental in positioning your team for a strong playoff run or the ultimate – a World Series championship. Unfortunately, that is an incorrect approach.

The best trades are the ones that prove successful for both teams. That may take several years to analyze, but that is the goal of any transaction. Both parties walk away with what they want and the players exchanged eventually reach their expected promise. The Boston Red Sox have made three notable transactions all involving pitching – Chris Sale, Craig Kimbrel, Drew Pomeranz and Tyler Thornburg.

The Red Sox moved prospects in all three deals and within each package were a promise that may or may not reach their full potential. Now for a look at just how the players shipped out have done to reflect on whether or not these deals would have been done in retrospect.

SEATTLE, WA – JULY 25: Starter Drew Pomeranz (Photo by Stephen Brashear/Getty Images) /

Drew Pomeranz for Anderson Espinoza was a No. 1 pitching prospect for an All-Star. A trade consummated between the Red Sox and Padres at the All-Star break in 2016. A risky proposition for the Padres hinging on projected growth. Anything can happen and for Espinoza it has. The diagnosis for the 19-year-old is “Right forearm tightness” and 2017 has been a shutdown season.

The Padres have been exceptionally cautious with Espinoza and it is doubtful he will pitch this season. Espinoza remains the No. 61 ranked prospect on MLB Prospect Watch and number five among San Diego prospects.

The Red Sox received damaged goods with Pomeranz. The Padres were rather secretive regarding health issues and when finally knowledge became available the Red Sox refused to negate the trade. As Pomeranz continued to register one dismal start after another the conclusion was the Red Sox have given away a prize for a broken down arm. Pomeranz finished the second half with a 4.59 ERA.

What a difference a year makes, as Pomeranz has become consistently reliable this season. Pomeranz now has attained double-digit wins and his ERA has shrunk to well under 4.00. So far the deal has been a plus for Boston, but if Espinoza reaches his projected promise that would certainly be altered. If Espinoza eventually becomes a reliable starter then the deal certainly falls into the category of a success for both teams. If this was a “win” situation, then Dave Dombrowski gets the first place prize – so far.

Would I have made the deal? No.

SAN DIEGO, CA – JULY 30: Manuel Margot (Photo by Denis Poroy/Getty Images) /

The Red Sox depleted the farm system depth somewhat with the deal with the Padres that brought Craig Kimbrel to Boston for several top prospects. The impact of Kimbrel is a season late, but even 2016, despite knee surgery and a horrendous 5.1 BB/9, was excellent none the less. A .151 batting average against showed Kimbrel is one tough pitching dude to hit.

This season Kimbrel has virtually eliminated his walks. The saves keep on rolling in and batters could consider a loud foul or any foul as a success against the hard throwing right-hander. The Red Sox got exactly what they wanted and so have the Padres.

Manuel Margot was the key piece for the Padres and the fleet outfielder is now the regular center fielder – a position that was in all probability not happening in Boston. Margot may some day be an All-Star. Margot is developing power and may eventually be a 15+ home run bat and when last noted was hitting in the .270 range.

Carlos Asuaje was another in that deal that is now on the MLB roster. Asuaje is considered best at second base but has played third and some outfield. Do not expect balls to be rattling off the fence with Asuaje, but he does have a nice left-handed stroke and is hitting over .300 for San Diego.

Left-hander Logan Allen – ranked No. 14 on the Padres list and left-handed hitting infielder Javier Guerra – unranked on the Padres list – are in A+ ball. Guerra has stalled and Allen was recently promoted to A+ ball.

Another transaction that has left both trade partners satisfied with the results. Boston had talent that was blocked by other talent – a better opportunity elsewhere for blocked players and that worked out rather well. Boston got one of the best at closer.

Would I have made the deal? Yes.

CHICAGO, IL – JULY 31: Yoan Moncada (Photo by Jonathan Daniel/Getty Images) /

The acquisition of Chris Sale was costly in prospects and monetarily as the Red Sox had paid a $31.5 million contract to Yoan Moncada and a matching penalty. When the transaction was consummated with the White Sox the Red Sox already were down monetarily to the GNP of a small country.

Sale is as advertised and quite possibly far better. The best pitcher in the majors and it is not even close. A left-handed Pedro Martinez is quite appropriate as Sale has been that dominant. Still just 28-years-old and under team control for 2018 and 2019. Sale – if he continues at his current pace – may finally corral a Cy Young Award, 20 wins, a possible MVP and the pitching version of the triple crown.

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When a Sale becomes available you do not hesitate, you pull the trade trigger and that means either MLB talent or the proverbial “Can’t miss” prospects. Moncada is now with the White Sox and despite a slow start will eventually succeed – just too good to fail.

The other important piece was hard throwing right-handed Michael Kopech. Kopech is the No. 12 ranked prospect on MLB Prospect Watch. Kopech is noted for two things: An ability to throw heat and to make questionable personal decisions. I will concentrate on the first.

Kopech is now in Double-A and honing his skills. With Kopech it is all about control as his 5.6 BB/9 suggests. Kopech is a rare talent and should in the next season or two fastball his way to the majors. Will he be as good as Sale? Sale also had a relatively high BB/9 that has shrunk through the years and maybe Kopech will follow the same direction?

A third prospect in the swap was switch-hitting outfielder Luis Alexander Basabe, who is in A+ ball and having – as they say – adjustment issues. Basabe has above average speed and excellent base stealing ability, but to steal one must get on base. Too many strikeouts and too few hits. Basabe is ranked 20th on the Chicago White Sox list of prospects.

This is a deal that shows profit immediate and profit delayed. In the short-term, the Red Sox may win a World Series or two keyed by Sale. The White Sox may have a five-tool future star in Moncada and an ace in Kopech. Expect this to be a solid “win-win” deal for both teams.

The last player is best classified as a throw in. Victor Diaz is a 23-year-old right-hander who is currently on the DL. Diaz has a fastball in the high 90s and projects as a possible reliever.

Would I have made the deal? Yes – Emphatically.

MILWAUKEE, WI – AUGUST 03: Travis Shaw (Photo by Dylan Buell/Getty Images) /

Occasionally a transaction becomes so one-sided it is just laughable and that is the deal that brought Tyler Thornburg to Boston from the Brewers. Thornburg has done nothing but test the diagnostic medical ability coast to coast.

Thornburg’s a pitcher who could give multiple innings and segue to Kimbrel. The reality is the ominous possibility Thornburg may never pitch. A healthy Thornburg and Smith would mean no need for Addison Reed.

Red Sox: A return look at four key deals. How is it working out?

The Boston Red Sox emptied out the prospect closet with a series of deals by Dave Dombrowski. Just how are those prospects doing? How are those deals looking?

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