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The Boston Red Sox made one of the biggest splashes on Monday's trade deadline day, acquiring All-Star catcher Adley Rutschman from the Baltimore Orioles in exchange for a massive prospect package, including pitcher Anthony Eyanson. The trade to acquire the three-time All-Star backstop was a massive gamble by Boston Chief Baseball Officer Craig Breslow; however, it was worth it.
Under Breslow's leadership, the Red Sox organization has accomplished something that they have failed to do for the better part of the 21st century: develop starting pitching. Whether it be identifying and acquiring pitchers or elevating prospects already in the system, Breslow's regime has done a remarkable job of building a pitching pipeline in Boston.
Since taking over as the head of baseball operations ahead of the 2024 season, Breslow has done a remarkable job drafting pitchers, like Payton Tolle, who was selected in the second round of the 2024 MLB Draft and Eyanson (a 2025 third-round selection), and elevating them into some of the best pitching prospects in the sport.
Pitchers Payton Tolle (left) and Connelly Early (second from left) stand for the national anthem ahead of Triple-A Worcester's game at Polar Park on Aug. 21, 2025. USA TODAY Network via Reuters Connect
Breslow has also been able to elevate pitchers who were already with the Boston organization prior to his arrival. Left-handed starter Connelly Early not only became one of the best pitching prospects in the sport, but one of the best young starters in all of baseball under the newfound Boston pitching lab before being traded to Washington for infielder Curtis Mead ahead of the trade deadline.
Then there are the Jake Bennetts of the organization, pitchers who were with other organizations that were identified as having another level to reach in the Boston organization. Breslow took a massive risk on Bennett, a relative unknown within the Nationals organization, trading fellow starter Luis Perales for the big left-hander. Bennett has, of course, become an incredibly valuable member of the Boston rotation, while Perales has posted a 3.76 ERA in Triple-A Rochester.
As a result of Boston's penchant for developing starting pitchers, Breslow has been more than willing to trade pitching both at the major and minor league levels. "Breslow has told Sox people, a team source said, that he believes strongly enough in their ability to backfill that he is OK trading depth pieces, even if they excel elsewhere," wrote Tim Healey of the Boston Globe on June 1.
Nov 2, 2016; Cleveland, OH, USA; Chicago Cubs president Theo Epstein holds the commissioner's trophy after game seven of the 2016 World Series against the Cleveland Indians at Progressive Field. David J. Phillip/Pool Photo via USA TODAY Sports
Those were the words from surefire Hall of Fame executive Theo Epstein after the Chicago Cubs traded for now-Red Sox closer Aroldis Chapman at the 2016 trade deadline. It has been seven seasons since the Red Sox last won the World Series, the longest championship drought since 2004.
Since the end of the 2019 season, Red Sox ownership had sold fans on a more sustainable future built on homegrown prospects. Prospects like Marcelo Mayer, Kristian Campbell, and others have not exactly panned out, returning Boston to true title-contender status in as timely a fashion as fans and ownership would have liked.
Nov 2, 2013; Boston, MA, USA; Boston Red Sox executives (left to right) Larry Lucchino, John Henry, and Tom Werner hold World Series trophies inside Fenway Park prior to the World Series parade and celebration. Bob DeChiara-USA TODAY Sports
According to MassLive.com's Sean McAdam, there was a "feeling from upper management and ownership that it's time to go for it." The move to acquire Rutschman, no matter how rich the cost, is undeniably a move made in hopes that it will deliver the fifth World Series ring during the Fenway Sports Group's time as owners.
Regardless of whether Rutschman signs an extension before hitting free agency after the 2027 season, or whether any of the prospects dealt go on to have great major league careers, winning cures all. If Rutschman contributes to bringing Boston their fifth World Series title, it will have all been worth it for Breslow.
The Red Sox are 64-52 and in third place in the American League East.
Continue reading...
A pitching pipeline
Under Breslow's leadership, the Red Sox organization has accomplished something that they have failed to do for the better part of the 21st century: develop starting pitching. Whether it be identifying and acquiring pitchers or elevating prospects already in the system, Breslow's regime has done a remarkable job of building a pitching pipeline in Boston.
Since taking over as the head of baseball operations ahead of the 2024 season, Breslow has done a remarkable job drafting pitchers, like Payton Tolle, who was selected in the second round of the 2024 MLB Draft and Eyanson (a 2025 third-round selection), and elevating them into some of the best pitching prospects in the sport.
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Pitchers Payton Tolle (left) and Connelly Early (second from left) stand for the national anthem ahead of Triple-A Worcester's game at Polar Park on Aug. 21, 2025. USA TODAY Network via Reuters Connect
Breslow has also been able to elevate pitchers who were already with the Boston organization prior to his arrival. Left-handed starter Connelly Early not only became one of the best pitching prospects in the sport, but one of the best young starters in all of baseball under the newfound Boston pitching lab before being traded to Washington for infielder Curtis Mead ahead of the trade deadline.
Then there are the Jake Bennetts of the organization, pitchers who were with other organizations that were identified as having another level to reach in the Boston organization. Breslow took a massive risk on Bennett, a relative unknown within the Nationals organization, trading fellow starter Luis Perales for the big left-hander. Bennett has, of course, become an incredibly valuable member of the Boston rotation, while Perales has posted a 3.76 ERA in Triple-A Rochester.
As a result of Boston's penchant for developing starting pitchers, Breslow has been more than willing to trade pitching both at the major and minor league levels. "Breslow has told Sox people, a team source said, that he believes strongly enough in their ability to backfill that he is OK trading depth pieces, even if they excel elsewhere," wrote Tim Healey of the Boston Globe on June 1.
If not now, when?
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Nov 2, 2016; Cleveland, OH, USA; Chicago Cubs president Theo Epstein holds the commissioner's trophy after game seven of the 2016 World Series against the Cleveland Indians at Progressive Field. David J. Phillip/Pool Photo via USA TODAY Sports
Those were the words from surefire Hall of Fame executive Theo Epstein after the Chicago Cubs traded for now-Red Sox closer Aroldis Chapman at the 2016 trade deadline. It has been seven seasons since the Red Sox last won the World Series, the longest championship drought since 2004.
Since the end of the 2019 season, Red Sox ownership had sold fans on a more sustainable future built on homegrown prospects. Prospects like Marcelo Mayer, Kristian Campbell, and others have not exactly panned out, returning Boston to true title-contender status in as timely a fashion as fans and ownership would have liked.
You must be registered for see images attach
Nov 2, 2013; Boston, MA, USA; Boston Red Sox executives (left to right) Larry Lucchino, John Henry, and Tom Werner hold World Series trophies inside Fenway Park prior to the World Series parade and celebration. Bob DeChiara-USA TODAY Sports
According to MassLive.com's Sean McAdam, there was a "feeling from upper management and ownership that it's time to go for it." The move to acquire Rutschman, no matter how rich the cost, is undeniably a move made in hopes that it will deliver the fifth World Series ring during the Fenway Sports Group's time as owners.
Regardless of whether Rutschman signs an extension before hitting free agency after the 2027 season, or whether any of the prospects dealt go on to have great major league careers, winning cures all. If Rutschman contributes to bringing Boston their fifth World Series title, it will have all been worth it for Breslow.
The Red Sox are 64-52 and in third place in the American League East.
Continue reading...
