Pirates Take a Chance on Outfielder Will Robertson in Early Offseason Move
As the offseason barely begins for most Major League Baseball teams, the Pittsburgh Pirates are already making roster moves to address one of their most persistent weaknesses. The Pirates’ outfield has been among MLB’s least productive offensive units for years, prompting the organization to pursue any potential improvement opportunity that comes their way. In this spirit, Pittsburgh has claimed 27-year-old outfielder Will Robertson off waivers from the Chicago White Sox, adding him to their 40-man roster while designating Ryan Kreidler for assignment to make space. This early move signals the Pirates’ determination to explore all avenues for improvement, regardless of how modest they might appear.
Robertson’s journey to Pittsburgh has been anything but straightforward. Originally drafted by the Toronto Blue Jays in 2019, he made his major league debut with them earlier this season, but his stint lasted only three games before being designated for assignment. The White Sox subsequently picked him up, where he appeared in 24 more games at the big league level. However, Chicago’s decision to outright four players from their 40-man roster, including Robertson, appears to be part of a strategy to protect prospects from the upcoming Rule 5 Draft rather than a direct reflection of Robertson’s potential. For the Pirates, this organizational shuffle by the White Sox presented an opportunity to add a player with remaining minor league options and potential upside.
While Robertson’s major league numbers don’t immediately inspire confidence—he slashed a meager .129/.179/.143 in his limited big league action this year—his Triple-A performance tells a markedly different story. In just 89 games at the Triple-A level this season, Robertson posted an impressive .958 OPS and blasted 20 home runs, suggesting there might be untapped offensive potential that hasn’t yet translated to the major league level. These minor league statistics likely factored heavily into the Pirates’ decision to claim him, as they represent the kind of power production that Pittsburgh’s outfield has sorely lacked in recent years.
The addition of Robertson represents a low-risk, potentially high-reward move for a Pirates team that needs to get creative with roster construction. With two minor league options remaining, Pittsburgh has the flexibility to develop Robertson further in their system if he doesn’t immediately earn a spot on the opening day roster. This kind of measured acquisition aligns with the approach many smaller-market teams must take: identifying overlooked talent, providing development opportunities, and hoping for breakout performances. For a player like Robertson, who has shown flashes of significant offensive capability in the minors, Pittsburgh offers a fresh chance to establish himself as a major league contributor.
The reality of this acquisition isn’t lost on Pirates fans, who have weathered years of bargain-bin roster moves with limited success. The fanbase’s skepticism is understandable given the team’s recent history, and Robertson will face an uphill battle to win over supporters who have grown weary of seeing their team shop primarily in baseball’s discount aisles. However, baseball’s unpredictability is one of its defining characteristics, and players who struggled in one organization regularly find success in new environments. Robertson’s impressive minor league numbers at least provide a foundation for optimism that he could become a productive player in the right situation.
As the Pirates continue their rebuilding process, moves like claiming Robertson highlight both the challenges and opportunities facing the organization. While Pittsburgh may not be competing for high-profile free agents, they’re actively seeking ways to improve around the margins—finding overlooked talent, developing it within their system, and hoping to uncover valuable contributors at minimal cost. For Robertson, Pittsburgh represents a genuine opportunity to reset his career and potentially become part of the solution for a team desperate for outfield production. While fan expectations may be tempered, baseball’s history is filled with unexpected success stories, and the Pirates are hoping Robertson might just become their latest diamond in the rough.
