How Pitching Has Ruined The Red Sox: Anatomy Of A Trade Part II

Featured Photo by Maddie Meyer/Getty Images

If you missed Part One of this series, you can click here to catch up. You can follow along as I analyze in-depth the anatomy of baseball trades in Boston and their long term affects. Today, we’re going to be focusing on the pitching situation for the Red Sox.

It is unquestionable that the Red Sox ended up in their current situation because of a toxic combination. That is, poor pitching development and the resulting need to take on veteran pitchers to fill in the gap. Veteran pitchers come with miles on their arms and are often more injury prone than a pitcher that is fresh off the farm.

If they’re not injury prone when they sign, there’s a real risk that they become injury prone during the course of their deal. Chris Sale and David Price are prime examples of this. Pitchers with minimal injury concerns before they arrived in Boston, but who became incredibly injury prone during their time here. 

Where It All Began

Jon Lester was supposed to be Boston’s ace, until a poor decision to trade him to Oakland in 2014. Photo by David J. Philip/AP Photo

The story begins back in 2010. The Red Sox had developed a solid core of position players, but they were not able to do the same on the mound. It certainly wasn’t for a lack of trying. Between 2010 and 2015, the Red Sox selected six pitchers in the first round of the draft.

None of them panned out as long-term starters. Only Matt Barnes ended up in a long-term role in the organization period.

The gem of the 2000s Red Sox pitching development machine was Jon Lester. He was supposed to be the new long-term ace in Beantown. However, he was traded away in 2014 and ended up signing a long-term deal with the Chicago Cubs in 2015.

Lester and Clay Buchholz are the last long-term starters to have been developed by the Red Sox. They both made their debuts back in 2007. 

In order to supplement their lack of pitching development, the Red Sox acquired Eduardo Rodriguez from the Baltimore Orioles in July 2014. Rodriguez was a young arm who had yet to make his major league debut. Yet, he looked to be a long-term asset for the organization.

Rodriguez’s time in the Red Sox minor league system was short, and he made his debut in 2015. Boston then went on a series of trades over the years to build their rotation. They acquired Rick Porcello in 2015, followed by David Price in 2016, Chris Sale in 2017, and Nathan Eovaldi in 2018.

Where Things Start To Go Wrong

Although an integral part to the 2018 team, Chris Sale’s extension has proven costly for Boston in the present day. Photo by David J. Philip/AP Photo

In 2018, the Red Sox spent $67.77 million on their rotation alone. They also had a total payroll of $223 million, $20 million higher than the second place San Francisco Giants. Rotation arms are expensive, and teams eventually pay the price for bad pitching development. 

In the aftermath of the World Series, Chris Sale signed a five-year, $145 million extension. On its face, this isn’t a terrible deal. Sale was still an elite pitcher, and losing him in free agency might have been devastating to any long-term plans to compete.

Sale was also dominant in 2018.  In 27 starts, he had finished 12-4 with a 2.11 ERA and 237 strikeouts. When healthy, Sale, Eovaldi, and Rodriguez were also a solid 1-2-3 at the top of the rotation.

Eovaldi had received a four-year, $68 million dollar extension. Rodriguez still had two seasons until he was due to hit the free agent market. If you wanted to extend the window of competition, you had to keep Chris Sale.  

However – note the use of the word healthy. For Eovaldi and Sale, this was a big caveat. 

Sale was not due to be a free agent after 2018. In fact, the extension didn’t even take effect until 2020. There was no pressing need to extend Sale and a multitude of other reasons not to do so yet.

The injury concerns that have plagued Sale over the last couple of seasons were beginning to pop up in 2018. He had two stints on the injured list in August due to shoulder concerns. There was all the reason in the world to wait and see if this was a blip on the radar or the start of a decline.

Of course, one could also understand Dombrowski’s rush. Sale didn’t have much of an injury history before August 2018, and if he continued to dominate in 2019, his price tag could only go up. Dombrowski had to weigh whether to extend now and sign Sale to a “team friendly” deal, or risk another dominant season where Sale could test free agency and drive his price up. 

The Red Sox made, what in retrospect, were multiple wrong choices.

They also ignored the injury concerns about Nathan Eovaldi. His 2015 and 2016 seasons had ended prematurely due to injuries. The latter injury caused him to need Tommy John surgery and miss the entire 2017 season. Dombrowski ignored these concerns and signed Eovaldi to a multi-year contract. 

In 2019, pitching wasn’t just bad. It was historically bad. The 2019 team remains the only Red Sox team in history to give up over 200 home runs. Their earned run total is the fourth highest in team history.

The pitching issues were a dead end. The team had never won a division while giving up more than 640 runs in a season. There is some evidence that the Sox could overcome less than stellar pitching. The 2004 and 2005 teams won a Wild Card berth while giving up 674 and 752 runs, respectively. These teams area outliers though, not a model for success. 

Chris Sale also had a major regression in 2019. His ERA increased to 4.40. He went 6-11, his Walks and Hits Per 9 Innings (WHIP) increased. His Home Runs per 9 innings (HR/9) increased. Sale’s season also ended prematurely in August. It was announced in March 2020 that Sale would undergo Tommy John surgery. 

Nathan Eovaldi went onto the injured list in April, needing surgery on his pitching elbow. He missed six weeks, came back into the bullpen in late July, and returned to the rotation in August. He finished the season with a 2-1 record with a 5.99 ERA. Eovaldi also saw a regression in all of his major statistical categories. 


Just one season after winning 108 games and setting a franchise record, the Red Sox missed the playoffs in 2019. The consequences of the failure to develop pitching and the need to sign arms that already had miles on them had started bearing fruit.

You can’t build a dynasty without pitching, no matter how good your position players are. The Red Sox had made some unfortunate decisions regarding pitcher extensions. If the Sox had waited a year to extend Sale, they would have likely gotten him at a lower price after his contract expired.

Had he Sox had let Eovaldi walk, they could have used the money that they paid him to sign a pitcher that, while possibly less talented, may have given then more innings and production on the mound. 

If Boston had actually developed good starting pitching, they wouldn’t have needed to make these moves. They would not have been forced to sign veteran arms and could have relied on younger pitchers to fill their rotation. Acquiring Nathan Eovaldi, David Price, Chris Sale, and Rick Porcello were desperation moves that were necessitated by a “win now” situation. They were not  moves that create a sustainable team.

The Red Sox were put in that position by their own failures to scout and develop pitching. If Henry Owens, Trey Ball, or Brian Johnson had reached the heights that their draft position indicated were possible, they could have easily saved $40-50 million on pitching, which could have altered the trajectory of the franchise.

There’s also the discussion of David Price – which will be covered more in-depth in the next part of this series. 

Trending This Week:

1 thought on “How Pitching Has Ruined The Red Sox: Anatomy Of A Trade Part II”

  1. Pingback: The Improbable Dream Part IV: Against All Odds – Guy Boston Sports

Leave a Reply