Boston Red Sox chief baseball officer Craig Breslow entered the offseason with a long list of tasks, but no single day was as active or as revealing of the organization’s intentions as Tuesday. As the 6 p.m. ET deadline for finalizing adjustments to the 40-man roster approached, Breslow and his front office did far more than routine housekeeping. Instead, they executed a sweeping sequence of moves that made it clear the Red Sox are aggressively reshaping the structure of their organization from top to bottom.
According to reporting from Chris Cotillo of MassLive, Boston’s day amounted to a full-scale overhaul. The front office completed four separate trades, added three minor-league pitchers to the 40-man roster, and parted ways with two recognizable contributors by designating them for assignment. For a single afternoon in November, the activity rivaled the type of movement seen at the trade deadline or just before spring training cuts.
The reason for the flurry of transactions is rooted in MLB’s roster rules: players in the minor leagues who meet certain service-time thresholds five years for those signed at age 18 or younger, and four years for those signed at 19 or older become eligible for selection in the Rule 5 Draft if they are not protected on a team’s 40-man roster. The Rule 5 Draft, scheduled this year for December 10, essentially allows other clubs to pluck unprotected players and add them to their major league rosters, provided they keep them there for the entire season. For an organization, it represents a risk of losing a player with upside before he ever reaches the big leagues.
Because of that, teams often face difficult decisions when deciding which players to protect. The Red Sox chose to safeguard three young pitchers Shane Drohan, David Sandlin, and Tyler Uberstine by adding them to the 40-man roster. Drohan has long been viewed as a potential depth starter with strikeout potential. Sandlin, acquired earlier in the year in a minor trade, possesses intriguing swing-and-miss capabilities that Boston believes can translate to higher levels. Uberstine, meanwhile, has improved steadily and showed enough growth in 2024 for the organization to feel uncomfortable risking his loss.
But the most surprising storyline of the day involved a talented but inconsistent prospect whom the Red Sox chose not to protect.
That player is Miguel Bleis, once viewed as one of the crown jewels of the club’s international pipeline. When Boston signed Bleis as a 16-year-old out of the Dominican Republic in 2021, they awarded him a $1.5 million signing bonus the largest they spent in that year’s international class. Scouts at the time were enthusiastic about his physicality, his athletic tools, and his loud on-field performance. MLB.com described him then as “one of the biggest and strongest prospects on the international market,” noting that he displayed advanced power, a refined approach, and the ability to impact the baseball with uncommon force for someone his age.
Their scouting report praised Bleis’s ability to drive balls into the gaps, his knack for hitting home runs during both showcases and competitive games, and even his early feel for the strike zone. His offensive polish, paired with his athleticism and strong arm in center field, made him one of the most exciting young players Boston had signed in years.
Four years later, however, the picture is much more complicated.
Bleis, now 21, has encountered challenges typical of many raw, toolsy prospects trying to climb their way toward the majors. His 2024 season demonstrated flashes of the power-speed potential that once made scouts enthusiastic, but he struggled to show consistency, particularly after being promoted against stiffer competition. At High-A Greenville, Bleis posted a .735 OPS respectable, particularly for someone with his developmental background. But when he was elevated to Double-A Portland on August 2, the gap between raw skills and polished production became more evident.
Over 110 at-bats with Portland, Bleis collected just 23 hits, managed only a single home run, and finished the stretch with a .554 OPS. Pitchers at the Double-A level frequently expose holes in a hitter’s approach, and for Bleis, the jump represented a significant test. The Red Sox still value his long-term upside, but his uneven performance made the front office hesitant to dedicate a precious 40-man roster spot to him, particularly when the team had other young pitchers they were not willing to risk losing.
This decision did not go unnoticed in the broader baseball scouting community. Jonathan Mayo and Jim Callis of MLB.com, two of the most respected prospect evaluators in the industry, labeled Boston’s choice to leave Bleis unprotected as the organization’s “toughest Rule 5 call.” They emphasized that while Bleis has experienced difficulties producing consistently, his physical tools remain elite within the Red Sox system boasting plus raw power, top-tier speed, and a strong throwing arm. Those traits still make him an intriguing development project, though they also acknowledge he has yet to translate those gifts into reliable results over a full season.
Bleis currently ranks No. 15 among Red Sox prospects according to MLB Pipeline and No. 18 according to the evaluators at SoxProspects.com. Both sources still believe he has major league potential and project his big-league ETA to be 2027 if he stays healthy and continues to refine his offensive game. But prospect rankings are not the same thing as roster decisions. For Boston, the ultimate question was whether his near-term risk of being selected in the Rule 5 Draft outweighed the opportunity cost of leaving someone else unprotected.
The Red Sox appear to have decided that while Bleis remains talented, his being chosen in the Rule 5 Draft is not guaranteed. In addition to raw upside, Rule 5 candidates typically need upper-level experience and some degree of readiness to survive on a major league roster for an entire season. Bleis, at just 21 and with only a small sample of Double-A experience, may not yet be an easy stash for another club. The Red Sox are betting that even rebuilding teams may hesitate to allocate a big-league roster spot to him for a full year.
Still, the move carries risk. International prospects who sign for seven-figure bonuses almost always receive extended opportunities and protection from their original organizations. Losing such a player in the Rule 5 Draft especially one as highly regarded as Bleis was upon signing would represent a significant organizational setback, not merely in developmental terms but also in how talent acquisition strategies are evaluated moving forward.
Meanwhile, the trades the Red Sox completed throughout the day further underscored Breslow’s determination to reshape the pitching infrastructure. While the specific deals varied in scope, they collectively reflected a clear pattern: accumulating arms with upside, shedding depth redundancies, and refocusing the organization around pitching development. Adding three minor-league pitchers to the 40-man roster in one day is unusual and suggests the Red Sox believe they are on the cusp of graduating a wave of homegrown arms or at least giving themselves more protection against injuries that have plagued the major league staff in recent years.
Additionally, the two players designated for assignment illustrated that Breslow is unafraid to make unpopular decisions when he believes they align with long-term planning. DFA’ing familiar contributors often signals a commitment to reprioritizing resources toward youth, versatility, or pitching depth.
While Tuesday’s transaction list may not immediately transform Boston’s big-league roster, it served as a strong indicator of how Breslow intends to steer the organization over the coming months. He has emphasized repeatedly that building a sustainable winner requires depth, internal pitching development, and difficult choices about which prospects to prioritize.
The Rule 5 Draft rarely attracts widespread fan attention, but in many ways it serves as a window into how franchises evaluate their own talent. By leaving Miguel Bleis unprotected while adding lesser-known pitchers, the Red Sox revealed their belief that pitching depth and protecting pitchers who may contribute sooner takes precedence over guarding a more distant, higher-variance prospect.
As the offseason continues, the ramifications of Tuesday’s decisions will become clearer. If Bleis is selected by another team, the Red Sox may face scrutiny for losing a once-highly-touted international signee for nothing more than a Rule 5 fee. If he remains in the system, Boston will retain the opportunity to re-evaluate him for another year, hoping that his immense raw talent evolves into tangible production.
Either way, Tuesday marked a defining early moment in Craig Breslow’s tenure one that showcased an assertive, proactive, and calculated approach to roster building, signaling that the Red Sox front office is fully engaged in shaping the organization’s future direction.
