Evaluating the Moves of Dealing Dave

It was announced recently that the Red Sox were the only team in MLB not to have a Top 100 prospect within their organization. Despite prospect capital, things are fine in Boston.

It’s no secret that the Red Sox lacked the plethora of ammo to make big splashes at the recent Trade Deadline. A flurry of trades, and notable graduations, since Dave Dombrowski took over as the President of baseball operations late in the 2015 season has left the farm system thin on assets.

However, the Red Sox organization has won the AL East the past two seasons, and currently has the best record in all of baseball. Dombrowski’s willingness to part with blue-chip prospects and recognize that Boston is a big market team, allowing them to pursue big money free agents, have this team in a position to contend for a World Series.

The farm system may take several year to get back to respectability, but we should look back on the trades that were made and see just how remarkable a job Dombrowski and company have done with our once prized minor league system.

November 13th, 2015:

Red Sox acquire closer Craig Kimbrel from the San Diego Padres for Carlos Asuaje, Javy Guerra, Logan Allen, and Manuel Margot.

The Red Sox were able to sure up the ninth inning duties by acquiring the the premier closer in all of baseball. At the time, Boston was left with an aging Koji Uehara and a couple of other misfits in Junichi Tazawa, Burke Badenhop, and Tommy Layne.

Dombrowski, and the Red Sox, had high hopes for Matt Barnes and Heath Hembree, but wanted to acquire an elite arm. In exchange for Kimbrel, they gave up a four player package that, at the time, were all prospects rated in the organizational Top 30.

Two and a half seasons later, Kimbrel just appeared in his third straight All Star Game with Boston (his 7th consecutive overall), while three of the four player he was traded for are struggling to find consistent playing time in the Major Leagues. The lone exception being Margot, who was the headliner in the package going to San Diego. While Margot has shown flashes of all star ability with the bat – to go along with outstanding center field defense – his cumulative WAR is still over a full win behind Jackie Bradley‘s over the same time frame that he’s been in the Major Leagues.

It’s rare that a 4 for 1 swap works out for the team acquiring the single player in a deal, but two and a half seasons later, this deal can be seen as a lopsided win for the Red Sox.

Verdict: Win

July 14th, 2016:

Red Sox acquire starting pitcher Drew Pomeranz from the San Diego Padres for pitcher Anderson Espinoza

At the time of this trade, Pomeranz was coming off of his first, and lone, All Star selection, finally fulfilling some of the potential that came along with being the 5th overall pick in the 2010 draft. There was some controversy surrounding his medicals after the trade, but the deal held up and he pitched to a mediocre 3-5 record with a 4.59 ERA to finish out the 2016 season with Boston.

Most of the baseball world was shocked that the Red Sox would give up Espinoza, who was rocketing up prospect ranking charts at the time of the trade. Young, and projectable, with increasing velocity with each appearance and advanced feel for his secondary pitches, the legendary Peter Gammons referred to Espinoza as the best teenage pitching prospect he’d seen in over two decades However, Espinoza would experience arm trouble of his own, undergoing Tommy John elbow surgery in early 2017, and has yet to return to the mound. While still just twenty years old, there is plenty of time for Espinoza to blossom into the future ace many have projected he will become.

Meanwhile, Pomeranz displayed the stuff of a frontline starter in 2017, going 17-6 with a 3.32 ERA, for the AL East champions. Pomeranz has not been able to replicate that success in 2018. He’s spent most of the season on the DL and has been ineffective while healthy, pitching to a 6.81 ERA.

At this time, it’s hard to judge the true outcome of the trade due to Espinoza’s lack of Major League service; however, the Red Sox acquired what they needed in Pomeranz. As of now, this is a win for the Sox, but that could change if Espinoza reaches his maximum potential in San Diego.

Verdict: To Be Decided

December 6th, 2016:

Red Sox acquire starting pitcher Chris Sale from the White Sox for Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz

The biggest rumors surrounding the 2016 Winter Meetings involved the White Sox and their attempt to pursue an aggressive rebuild through adding blue chip prospects for proven commodities, including Chris Sale.

On the final day of the meetings, Dombrowski pulled the trigger on one of the biggest prospects for superstar packages in recent history. In one of the more underrated moves of the Dombrowski era, “Dealing Dave” sent Moncada, a Cuban born player that Boston made the highest paid international free-agent signing ever, to the White Sox, along with Michael Kopech, the Sox highest rated pitcher, and also a top 30 overall prospect – along with 2 other high-upside minor leaguers.

In Boston, Sale has been nothing short of spectacular. He’s arguably the best starting pitcher in all of baseball and has added more velocity this season than ever before. It would not be unlikely to see him win his first Cy Young award this season.

Moncada has made it to the big leagues and looks like he’s there to stay, but his horrendous strikeout ratio and his inability to draw a walk doesn’t play well in today’s game. Meanwhile, Kopech continues to be a highly rated in the prospect rankings. His fastball is among the best in all of the minor-leagues, but his lack of plus secondary pitches, and his inability to consistently find the strike zone have taken away some of the shine that he had just a season ago. Basabe played in the 2018 Sirius / XM Futures Game, and is on track to find a role with the very young, rebuilding White Sox in the near future. Diaz is a fringe prospect that, at age 24, is unlikely to make a major impact on the organization.

The jury is still out on the prospects sent to Chicago, but the excellence that Sale has brought to Boston validates Dombrowski’s aggressiveness. If he signs an extension, this will be a major win for the Red Sox regardless of how the prospects pan out.

Verdict: Win

Aggressiveness Rewarded

Dave Dombrowski has made a few other moves including the Travis Shaw / Tyler Thornburg swap that have drawn speculation; however most are unable to be determined as of yet. It’s been clear as of late that Thornburg can be a proven reliever in the Red Sox bullpen, while Shaw has had a solid career in Milwaukee. This may immediately look like a loss for the Sox, but it will be interesting to see how the rest of this year pans out.

Additionally, Dombrowski made a few shrewd moves this season by acquiring Steve Pearce, Nathan Eovaldi, and Ian Kinsler for a total of 4 Top 30 prospects. Only one was near the top 10 (Jalen Beeks), while the others were considered fringe prospects at best.

Despite the criticism he has drawn, the aggressive GM has primed the Red Sox for a World Series run this October.

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