Breslow’s proven to be problem solver on and off field

That combination of traits — what former Red Sox general manager and Cubs president of baseball operations Theo Epstein described as “a fearless approach to problem solving” — helped Breslow forge a 17-year professional playing career that could have been over almost as soon as it began, allowed him to play a transformative role in the Cubs organization, and has led the Red Sox to entrust him with the keys to their baseball operations department.

The baseball career that nearly wasn’t

While scouts poured into New Haven during Breslow’s junior season in 2001, it wasn’t to see the undersized lefthander. Instead, teammate Jon Steitz, who featured a mid-90s sinker and slider albeit with inconsistent command, drew the evaluators.

Still, Breslow earned his notice, missing bats and drawing raves for his makeup as Yale’s captain as a senior in 2002. The Brewers, who had drafted Steitz in the third round in 2001, made Breslow their 26th-round pick in 2002.

But after struggles at two levels of Single A ball in 2003 and 2004 led the Brewers to release Breslow, he was confronted with a choice.

“He was like, ‘Should I quit, should I go be a doctor?’ ” recounted Orioles GM Mike Elias, Breslow’s teammate at Yale. “To his credit, he knew that he had the talent to pitch in the majors, so he went to independent ball.”

With an assist from Yogi Berra — whose locker at the Montclair Golf Club was by that of Breslow’s agent, Robert Baratta — Breslow landed a spot with the New Jersey Jackals of the Northeast League. He posted impressive strikeout numbers, earning a spring training tryout with the Padres in 2005.

The Padres offered Breslow a spot in their minor league system, which he accepted — with a condition. He would take only a spot in Double A; otherwise, rather than risk of stagnating in High A, he’d enroll at NYU in the fall.

It was an audacious suggestion, but it underscored Breslow’s determination to shape his own career rather than drifting. The Padres relented, acquired his rights from the Jackals for $1, and sent Breslow to Double A Mobile.

He emerged as a Southern League All-Star and got called up to the big leagues by midsummer of 2005, forging a 2.20 ERA in 14 relief appearances while shuttling between Triple A and the majors.

Though he was non-tendered that winter by the Padres to clear a spot on the 40-man roster, he’d done enough to position himself as a viable major league depth option — and sometimes more than that.

Nothing taken for granted

Despite his longevity — and at times excellence — as a pitcher, Breslow never took his position in the game for granted.

By the time he signed a minor league free agent deal with the Sox prior to the 2006 season, he’d already been released and non-tendered, promoted, and optioned. In 2008 and 2009, he pinballed between teams three times via waivers before finally gaining a foothold with the A’s from 2009-11.

He then got traded twice in an eight-month span, going to Arizona in the 2011-12 offseason before getting dealt to the Red Sox at the 2012 deadline.

Once back in Boston, Breslow enjoyed a reprieve from that nomadic existence. After the 2012 season, the Red Sox signed him to a two-year deal with a team option for 2015, seeing his combination of talent and clubhouse contributions as a fit for a team trying to recover from the wreckage of a year under Bobby Valentine.

Breslow delivered everything the Sox had hoped for in 2013 as a key setup man in front of closer Koji Uehara. He forged a 1.81 ERA over 61 regular-season appearances as the Sox unexpectedly flourished in a first-place season, then he opened the playoffs with seven straight high-leverage scoreless appearances before hitting a wall in the World Series.

During that time, Breslow’s focus was very much on the field rather than his post-playing career. Nonetheless, there were glimmers suggesting how his contributions to the game might outlast his time as a pitcher.

Breslow was a tinkerer who wasn’t afraid to change how he approached his craft. He’d change pitch mixes, grips, and release points, turning dials in search of combinations that would yield success.

“I definitely saw something unique with Bres,” said Red Sox farm director Brian Abraham, a bullpen catcher for the team in 2013. “He was always a voice that spoke up and could see the game in a different way.

“It was kind of the early stages of pitch design, just without some of the data and information. ‘If I do this, then the ball will do this. If I do this, then the ball will do that.’ I hadn’t been around that as much, I guess, so it stood out to me. It might have been common elsewhere, but for me, it was something that was unique.”

So, too, was the way Breslow pursued the continuation of his career. The Sox did not exercise their option on him after the 2014 season, making him a free agent. Instead of waiting for his agent’s phone to ring, Breslow joined Baratta at the Winter Meetings that year in San Diego, with the two cleverly staking out a table next to a Starbucks — which guaranteed face time with nearly every executive in the game.

That marked the first of several consecutive winters in which Breslow attended the meetings in person as a player, building his network.

His eyes were increasingly open to the directions in which the game was going — and to his uncertain future as a player. After re-signing with the Sox and having an up-and-down 2015 season, he landed a minor league deal with the Marlins for 2016. He spent about six weeks in the big leagues before getting designated for assignment and outrighted to Triple A, his career reaching an apparent crossroads.

Into the pitching lab

Breslow wasn’t passive about the potential end of his career. Instead, he stepped back and embraced a chance to problemsolve. The way he was pitching was no longer valued by teams, so he changed it.

In the offseason of 2016-17, Breslow reinvented himself in a way that anticipated the growth of so-called pitching labs in the game today. He took a data-driven approach to changing his arm slot — lowering it by about 9 inches — and overhauling his pitches from a four-seam/cutter/ changeup combination to a sinker/breaking ball/changeup mix to recreate himself as a left-onleft specialist.

“He was trying to find an angle where he could create pitches that were different enough to be effective at the major league level, and he was using technology to try to test himself against major league pitchers who did something like that,” said former Red Sox and current Pirates GM Ben Cherington. “It literally was like a science project.”

The overhaul led to a number of offers, and Breslow ultimately signed with the Twins. Though he was hardly dominant, his willingness to engage in datadriven change prolonged his career, as he split 2017 between Minnesota and Cleveland, then spent another year pitching in Double A and Triple A for the Blue Jays.

A pivot to the front office

Breslow never got back to the big leagues in 2018. After a year of riding buses with Blue Jays upper-levels prospects Vladimir Guerrero Jr., Bo Bichette, and Cavan Biggio (among others), he was ready for a new phase in the game.

But Breslow did not wait for someone else to write his next chapter. He wanted to take primary authorship. Instead of simply interviewing for available jobs, he wanted to take part in producing his own job description.

That stance put off some — notably, according to multiple MLB sources, the Red Sox. Breslow interviewed with Dave Dombrowski and other members of the Boston front office. It became quickly and mutually evident that there wasn’t a fit for the broad role he sought.

The Cubs, however, viewed Breslow as a special case who deserved special treatment.

“It sort of felt like he had been in grad school the whole time even though he had been playing,” said Cubs president of baseball operations Jed Hoyer. “Despite the fact that he’d just been playing for all that time, he really had a feel for kind of organizational structures, how to build things out, how to articulate his thoughts.”

Breslow worked with Epstein and Hoyer (then the GM under Epstein) to create a role that would make an impact and offer exposure to a wide array of front office responsibilities to further his growth. The Cubs hired him in January 2019 as their director of strategic initiatives.

“Usually, guys are excited to have one offer; he kind of had his pick of places,” said Hoyer. “We just kept talking to him during the process. Thankfully we got the rose.”

By the end of the year, the Cubs named Breslow director of pitching, charging him with the transformation of an organization that (like the Sox) ranked as one of the worst at developing pitching.

Some longtime Cubs officials and instructors felt uneasy about significant changes in philosophy (putting development of velocity and stuff in front of strike-throwing) and approach (technology- and data-driven pitch design and development).

Breslow didn’t shy from that reality. He wasn’t afraid to break some eggs, having direct conversations about what was needed to change direction and, in some cases, replacing individuals who weren’t on board. That said, in the majority of cases Breslow found people who adapted.

“One thing that jumps out to me is his empathy as a leader,” said Cubs vice president of player development Jared Banner. “I think he does a good job connecting with his colleagues and creating organizational buy-in.

“Any time you come into an organization with new ideas the way he did, there’s a chance that some skepticism follows. I think he was able to navigate that exceptionally well and ultimately create impressive alignment.

“Everything that he says has evidence behind it. It’s backed up by the data and information we have available. It’s even more poignant when that philosophy is coming from someone with that much big league service.”

The next frontier

While Breslow’s primary responsibilities — both in his initial director role and then as an assistant GM for the last three years — related to pitchers, his job quickly encompassed more of the team’s operations, even as he spent much of the season working from home in Newton.

When Breslow wasn’t with the team in Chicago, Hoyer talked to him nearly every day. Though he had limited contact with agents and executives of other teams, Breslow was part of Hoyer’s inner-circle decisionmaking on virtually every matter, from development and performance infrastructure to trades and free agents.

Breslow hasn’t lived day-today life inside a front office. He hasn’t experienced the daily inperson encounters with colleagues, owners, coaches, and players. As he prepares to lead the Red Sox’ baseball operations, he will be confronted with circumstances that are new to him.

“The fire hose is on for anybody when they’re first in that job,” said Cherington.

At the same time, such a challenge is very much in line with how Breslow has navigated a multi-tiered baseball career that has lasted more than two decades.

Elias doesn’t believe Breslow’s front office inexperience will be a significant issue.

“There’s 17 years of playing experience — that counts for a lot — while other candidates were probably toiling in different corners of the game,” he said. “All of that major league experience for somebody as observant and inquisitive as he is provides a lot of experience there.

“He’s just a well-rounded, impressive person. I think it’s an excellent, excellent hire for the Red Sox. I’m sure they’re thrilled that this worked out. From my standpoint, I’m looking forward to it. I think it’ll be a lot of fun. But I wish he was in a different division.”