To call Dave Dombrowski, one of baseball’s top and most successful executives, overrated is rare in the baseball world. He has spent years in Major League Baseball and is one of the top minds in the game.

As President of Baseball Operations for the Boston Red Sox, Dombrowski has executed his fair share of explosive moves and signings and guided the team to the playoffs in the year-plus since he took the reigns of the Red Sox from former general manager Ben Cherington. Dombrowski has made lots of flashy transactions, but the success rate has not been high.

The real point to ponder comes down to how much of last year’s success can be accredited to Dombrowski and what kind of team he has made them into for the future.

When Dombrowski arrived in Boston back in the late days of August 2015, it was a real change in mindset inside the Red Sox front office. Within a matter of days, the team went from being sabermetric heavy and hesitant to pay a pitcher who was over 30 years old (Jon Lester) to being almost all-in on every flashy free agent and every attractive guy on the trading block.

In November 2015, with the San Diego Padres falling apart after a huge offseason the winter prior, Dombrowski capitalized on this opportunity by trading for highly coveted closer Craig Kimbrel. To get Kimbrel, Dombrowski sent over four prospects: outfielder Manuel Margot, infielders Javier Guerra and Carlos Asuaje, and left-hander Logan Allen.

Kimbrel came to the Red Sox from San Diego. (April 2, 2017 – Source: Maddie Meyer/Getty Images North America)

Disregard the potential and success of those four prospects for a second. Dombrowski gave up four prospects for one 60-inning-a-year pitcher. Most teams don’t even trade for a closer, let alone trading a large number of prospects for one.

Margot was a top outfield prospect at the time for the Red Sox. He’s currently thriving with the San Diego Padres. Through 31 at-bats, Margot is batting .323 with two home runs. Since there would have been a logjam of outfielders had Margot stayed on staff, it made perfect sense for Dombrowski to trade him. It just wasn’t worth it to trade such a valuable prospect for a closer. He could have easily sent Margot away for a really good number-two or -three starting pitcher, or possibly even a number-one.

Since coming to the Red Sox, it appears as if Kimbrel just whips the ball at home plate and hopes for a strike. He’s 33-for-35 in save opportunities since coming to Boston, which is very good, but he has been horrid in non-save situations.

Just a few weeks after the trade for Kimbrel, Dombrowski broke the bank for David Price.

Price was the hottest commodity that offseason and most in Red Sox Nation wanted him in the worst way. After the previous administration lowballed Lester and then dealt him away, the new administration strived for an elite, top-of-the-line starter. And with Price, they thought they had that.

To outbid other teams, Dombrowski decided to offer up a whopping $217 million over seven years for Price, the largest contract ever for a pitcher. Price would have gone to the St. Louis Cardinals, but he could not refuse Dombrowski’s monstrous contract offer.

In Price’s first season with the team, he went 17-9 with an ERA of 3.99. It was one of his worst years of his career. He has yet to pitch in a game this season due to an arm injury he suffered back at the end of February. The Red Sox feared that Price needed Tommy John surgery, but those fears temporarily went away after a visit to Dr. James Andrews.

Price isn’t expected back until the end of May.

In the midst of a playoff race last season, Dombrowski felt he had to make a move for a starting pitcher. In mid-July, Dombrowski sent top pitching prospect Anderson Espinoza to the Padres for left-handed pitcher Drew Pomeranz. Pomeranz was in the midst of an All-Star season, but he had absolutely no track record to prove he could continue his dominance for the rest of the season, let alone years to come.

In 13 starts for the Sox last year, Pomeranz went 3-5 with a 4.59 ERA. He completely tanked in the second half and was a shell of his first-half self (2.47 ERA in his first 17 starts). Later in the season, the Red Sox found out the Padres hid medical information about Pomeranz from them. Pomeranz had been dealing with a left forearm flexor strain since the end of last season and began this year on the disabled list.

Pomeranz came to the Red Sox from San Diego. Sept. 17, 2016 – Source: Rich Gagnon/Getty Images North America)

Espinoza was a top-20 prospect in baseball and Dombrowski traded him for a guy who pitched like an injured number-four or -five pitcher.

During this past offseason, Dombrowski had a day in which he made two very big moves.

He began the day by dealing for right-handed reliever Tyler Thornburg. To get him, Dombrowski sent starting third baseman Travis Shaw, shortstop Mauricio Dubon, and right-handed pitcher Josh Pennington to the Milwaukee Brewers.

Similar to the Kimbrel deal, why would Dombrowski give up two prospects and a young, starting third baseman with potential in exchange for a setup man? Setup men are typically bred in the farm system and can be very inconsistent moving from team to team. To go along with that, Thornburg has an awkward, irregular throwing motion that can be very open to arm injuries — just like Carson Smith, who was also acquired by Dombrowski.

Smith needed Tommy John surgery last year and won’t be back until June.

Later that day, Dombrowski pulled off the biggest trade of the offseason by acquiring left-handed pitcher Chris Sale. To get Sale, Dombrowski had to empty the vat of top prospects by dealing away top infield prospect Yoan Moncada, pitching prospect Michael Kopech, and minor leaguers Luis Alexander Basabe and Victor Diaz.

There’s no such thing as an overpay for a pitcher who is as elite as Sale is. However, they did give up a lot. 

Moncada was their number-one prospect heading into the 2017 campaign, and Kopech had a lot of potential despite his troubled past. He has thrown his fastball well over 100 miles per hour. In theory, he would have been the perfect closer or setup candidate for the Red Sox bullpen.

The Sale trade was a good one for the Red Sox, but one has to wonder how much the Red Sox have left in their farm system. Dombrowski inherited the number-one farm system in baseball back in 2015. Bleacher Report’s pre-2017 season farm system rankings had the Red Sox at number 18. In less than two years, Dombrowski has skinned the farm system.

It’s clear that the Red Sox are trying to win now, but every team wants to have it be sustained. Dombrowski has a history of depleting farm systems because that’s exactly what he did in Detroit with the Tigers.

The problem with Dombrowski’s job thus far is that he’s made a lot of trades and had some major signings, but none are smart. For two relievers, Dombrowski traded seven players away (an everyday third baseman, a top outfield prospect, and five other minor leaguers). He’s currently paying $31 million per year for a so-far underachieving and injured starting pitcher. He also traded away one of the leagues top prospects (Espinoza) for a number-four starter (Pomeranz).

These are deals and signings that seem thoughtless; throwing $217 million at a pitcher or top prospects at a team will definitely bring the desired commodity in return. But why not try to be crafty and not give up as much?

The Red Sox are set to win for the next few years, but the most telling time will be after those few years are up and holes begin to emerge within the team.

Leave a Reply