Although the Boston Red Sox did not land some of the biggest names available on the free agent market this winter including third baseman Alex Bregman, along with marquee hitters like Pete Alonso, Kyle Tucker, and Kyle Schwarber the organization still earned high praise for its offseason strategy.
In fact, ESPN graded Boston’s winter work an “A” when evaluating all 30 Major League Baseball clubs, signaling that the front office’s broader vision resonated positively with analysts despite bypassing several headline grabbing bats.
Rather than committing massive long term contracts to star position players, chief baseball officer Craig Breslow opted for a different approach. He focused heavily on reshaping the roster through trades, prioritizing pitching depth and versatility. Breslow demonstrated a willingness to part with some of the organization’s top prospects in order to acquire established major league contributors who could address immediate needs.
Among the most notable additions were veteran right hander Sonny Gray and fellow pitcher Johan Oviedo, both brought in to strengthen the rotation and provide innings stability.
Breslow also acquired infielder Caleb Durbin, first baseman Willson Contreras, and versatile defender Isiah Kiner-Falefa. These moves reflected a clear organizational philosophy: balance the roster with experienced talent while maintaining flexibility.
Still, according to veteran Red Sox insider Sean McAdam of MassLive, the club’s offseason maneuvering may not yet be complete. As spring training games begin in both Arizona and Florida, Boston’s front office remains active behind the scenes. McAdam reported that the Red Sox are continuing to evaluate ways to bolster their bullpen specifically from the left side.
The team’s interest in left handed relief help appears genuine and ongoing. Scouts are reportedly attending games and observing back field workouts across rival camps, closely monitoring available southpaws who might fit Boston’s needs. Even as exhibition play gets underway, the front office is leaving no stone unturned in its search for additional bullpen depth.
Ironically, the Red Sox entered the 2025 season with a strong supply of left handed relievers. However, Breslow’s broader roster overhaul led to significant turnover. He traded away Brennan Bernardino and Chris Murphy, two southpaws who had contributed in recent seasons. Meanwhile, veteran left handers Justin Wilson and Steven Matz were allowed to depart via free agency.
That attrition has left Boston thinner on the left side than it was a year ago. Although the organization boasts two highly regarded left handed pitching prospects Payton Tolle and Connelly Early there is no current plan to move either into a permanent bullpen role.
Baseball America ranks Tolle and Early as the organization’s No. 1 and No. 3 prospects, respectively, underscoring their long term importance. Both are viewed primarily as starters, and Breslow along with manager Alex Cora appear intent on preserving their development in that capacity rather than accelerating their timelines by shifting them to relief.
Given that internal options are unlikely to fill the need, speculation naturally turns toward potential trade targets. One name that has surfaced is JoJo Romero of the St. Louis Cardinals.
The connection is intriguing for multiple reasons. Chaim Bloom Breslow’s predecessor in Boston now serves as the Cardinals’ top baseball executive, creating a familiar working relationship between the two front offices. Breslow and Bloom have already completed two deals this winter, involving Sonny Gray and Willson Contreras.
Stephen Parello of BoSox Injection has suggested that a third transaction between Boston and St. Louis could center on Romero, a 29 year old left handed reliever coming off a breakout campaign. Romero is currently playing on a one year contract worth $4.3 million, making him financially manageable and potentially attractive as a short term solution.
Romero’s 2025 season represented the best stretch of his six year major league career. Across 65 appearances totaling 61 innings, he posted a sparkling 2.07 earned run average. He also registered eight saves and struck out 55 batters all career highs. For a team seeking reliable left handed bullpen support, those numbers certainly stand out.
Of course, Romero is not without imperfections. Parello noted that he can be prone to issuing walks at times, and his elite production is limited to one standout year rather than a long track record of dominance. That inconsistency could temper his trade value or make Boston cautious about overpaying. Nevertheless, his recent performance suggests he has the tools to thrive in high leverage situations.
Another factor influencing Breslow’s potential interest could be strategic timing. Because Romero is under contract for just one season, he could serve not only as an immediate bullpen upgrade but also as a potential trade asset at the deadline.
If Boston finds itself out of contention, Romero could be flipped to a contender for prospects. Conversely, if the Red Sox are competing, he could remain a key late inning arm for a playoff push.
This dual purpose flexibility aligns with Breslow’s apparent roster building philosophy, maintain optionality. Rather than locking into long term commitments, the front office has emphasized moves that preserve adaptability.
The acquisitions of Gray and Contreras added veteran presence without completely sacrificing future maneuverability. Adding Romero would fit that pattern improving the present while keeping future pathways open.
It is also worth noting that Breslow’s offseason approach has been methodical rather than flashy. While fans may have hoped for a splash signing like Bregman or Alonso to energize the lineup, the front office instead focused on pitching infrastructure and defensive versatility. That strategy suggests a belief that run prevention and roster balance will yield more sustainable results than chasing star power alone.
Manager Alex Cora’s role in these decisions should not be overlooked. Maintaining two elite left handed prospects in starting roles reflects a coordinated organizational plan. Cora’s bullpen usage philosophy often emphasizes matchup flexibility, making a dependable left handed reliever particularly valuable in high pressure American League East contests.
If Boston ultimately executes another trade before Opening Day, it would cap a winter defined by calculated aggression in the trade market. Breslow has already demonstrated a willingness to part with promising prospects to address immediate weaknesses. Whether he believes Romero or another left handed reliever is worth the cost will depend on internal evaluations and how the market unfolds during spring training.
For now, the Red Sox find themselves in an interesting position. Despite passing on several marquee hitters in free agency, external evaluators have applauded their offseason body of work. The “A” grade from ESPN suggests that analysts view the roster as improved, more balanced, and strategically constructed.
Yet Breslow appears unwilling to stand pat. The ongoing scouting of left handed relievers indicates that the front office views bullpen depth as the final piece of the puzzle. If a deal materializes, it would further reinforce the theme of proactive roster shaping.
Ultimately, Boston’s offseason tells a story of calculated risk taking and disciplined prioritization. Rather than chasing the brightest lights of free agency, the Red Sox concentrated on building depth, versatility, and pitching stability. Whether that blueprint translates into regular season success remains to be seen, but the foundation appears thoughtfully constructed.
Should JoJo Romero become the next addition, it would mark yet another example of Breslow leveraging relationships and market opportunities to fine tune his club. And if not Romero, it seems increasingly likely that some left handed bullpen reinforcement will arrive before the games begin to count.
In the meantime, as spring exhibitions commence across the league, Boston’s scouts remain vigilant a sign that even after earning top marks for their winter efforts, the Red Sox are still searching for ways to get better.
