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Boston Red Sox: Yankees trades highlight stark difference in front office

While Brian Cashman dominated the trade market, Dave Dombrowski was once again found wanting. Is Boston's front office holding them back in the AL East?

At the start of 2017, the Boston Red Sox were the most talented team in the AL East and expected to waltz to a division title and October ball.

There are many reasons why that hasn’t happened, from injuries and player regression in Fenway to surprises around the rest of the division, but one of the biggest reasons the Red Sox juggernaut has not materialized is the man that runs the show, Dave Dombrowski, being out-maneuvered by his counterpart in New York.

Inheriting a fixable mess

No one who runs a baseball team gets every decision right. Let’s start from that position and understand that mistakes and misjudgments happen. However, when expectations are high and you are trying to build on three World Series titles in the 21st-century, mistakes have to be minimized.

Let’s begin with what was inherited from Ben Cherington’s successful yet dreadful time in charge. That includes the albatross that was Pablo Sandoval and the less than impressive Hanley Ramirez. However, Cherington also left behind a core of players that included Xander Bogaerts, Mookie Betts, Eduardo Rodriguez, Travis Shaw, Henry Owens, and Christian Vazquez.

Since Dombrowski took over exactly two years ago some of those players have become key pieces and impressive baseball players. Bogaerts boasts one of the best gloves at shortstop, and Betts was an MVP-contender in 2016. However, like all young prospects, some haven’t worked out as well as they could have.

The problems, though, stem from how Dombrowski tried to make the pieces fit together.

The Tyler Thornburg trade

Hindsight is 20:20, and it looks like the Red Sox well and truly had their pants pulled down in this one. It’s the trade that many point at as Dombrowski’s worst piece of business ever. After playing 145 games at third in 2016 for the Red Sox and slashing .242/.306/.421 with 16 homers, Dombrowski looked at his roster and decided to trade Shaw away. After all, he had the expensive Sandoval to fit into the lineup at third.

So he flipped Shaw to the Brewers for RHP Tyler Thornburg, to help build a strong bridge to Craig Kimbrel. The theory was good, the execution was terrible. Shaw has turned into a wonderful player in Milwaukee, while Thornburg, who was coming off a career-year in 2016, is yet to pitch for Boston, having had surgery for thoracic outlet syndrome.

Meanwhile, Sandoval has become even more of a trainwreck and been released, leaving a black hole of offense at third base for much of the year while Shaw is slashing .294/.366/.571 for the Brewers and his 24 homers would lead the Red Sox.

No one could have foreseen the issue for Thornburg, but trading even the 2016 version of Shaw, nevermind this year’s progression, for a 60 inning reliever is madness when you were relying on the shockingly poor Sandoval to fill the spot.

The David Price signing

$217 million is a lot of money. For a player with 1,441.2 regular season innings on his arm it’s a lot of risk. Price had long been a thorn in the side of the Red Sox, and the Sox did need a new ace in their rotation, but like a lot of things Dombrowski has touched, this deal did not work out.

The Boston fans and media can be an unforgiving, unpleasant, and downright awful group of people. And Price immediately received their ire by posting his highest season ERA (3.99) since 2009. His 2017 has been little better, and a spat with Dennis Eckersley has only served to create a storm of negative press around him. At 31, Price should be at his peak, but a nagging elbow issue, run-ins with the local media, and a seeming distaste for the place has him looking very much like another Carl Crawford.

The good parts

Not all of Dombrowski’s moves have been dreadful. Trading for Chris Sale, necessitated in part due to Price not working out, has been great and will probably see another Cy Young come to the Red Sox this season. The move to get Drew Pomeranz last year is working out as well. The young lefty has bedded in well with Boston and is putting up a strong 2017 campaign.

He’s also not emptied the farm system in doing so. While trading for Sale took some big pieces from the top of the farm, Rafael Devers is now in the Majors and doing well. However, the good has been overshadowed by the bad and the things he was unable to get done…

Cashman & the Yankees

In Boston, there is one rule: Beat New York. And Dombrowski is very much not doing that.

2017 was supposed to be an easy victory for the Red Sox over their hated rivals. However, without Thornburg, with that black hole at third, with no David Ortiz, and a general lack of power in the lineup, the Red Sox haven’t been as dominant as they were thought to be. Meanwhile, the Yankees have been resurgent thanks to the emergence of Aaron Judge, the continued brilliance of Gary Sanchez, a strong bullpen, and impressive seasons around the field. Injuries slowed them, but they are still chugging away, and at the trade deadline did what Boston could not. They got markedly better thanks to their brilliant supremo Brian Cashman.

They swiped Todd Frazier out from under the Sox’s nose, along with a pair of quality bullpen arms, then went out and added Sonny Gray for the next 2.5 years at least. All while holding onto the top of their farm system. This season was just another display of stellar work from Cashman and has probably cemented his status as the best GM in the sport.

In a vacuum, Dombrowski has made a few more mistakes than normal, with hindsight showing up a lot of his decision making. The “the sky is falling” mentality of Boston fans and media has made some of them out to be worse though. Pablo Sandoval is not his fault, and Price’s unhappiness in Boston is not something that could have been easily foreseen, however when the first comparison made is against the best around, it’s always going to be a rough time. Cashman’s brilliance in New York has only shone a light on the things that Dombrowski has gotten wrong in Boston.

Does Dombrowski need to go?

Maybe. I’m not so sure there is much he could have done better though. All big-money free agents carry risk, but plenty of teams were in for David Price. No one could have known about Thornburg’s issues or Shaw’s explosion into a leading star. However, some issues have been readily apparent. The loss of David Ortiz was never adequately accounted for, and a power bat will surely be #1 on the priority list this winter. However, losing to New York when a win was supposed to be all-but guaranteed means he might not get to call the shots when the market opens up. Especially if Boston misses the playoffs altogether.

There has been some poor play on the field from supposed stars in recent weeks, and manager John Farrell has been far from flawless, but the buck stops at the guy who builds the roster, and while Boston hold a four-game lead in the wild card race, their place in the postseason is looking far less safe than it did just a few weeks ago.

The trade deadline was not kind to Dombrowski and the Red Sox, and they need to find another gear or risk an embarrassing return from a season that promised so much.

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Toby Durant

A passionate and opinionated writer, I am currently the NFL editor for RealSport. However, I also contribute to F1, WWE, Football, and other sections of the site, and I have covered the NFL International Series for RealSport and previously contributed to SB Nation.


I also have 10 years playing and coaching experience in American football, starting at the University of Nottingham and including a stint as defensive coordinator at Oxford Brookes University. I may be a Patriots fan but all aspects of the sport interest me, from guard play to special teams.

Boston Red Sox: Yankees trades highlight stark difference in front office

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