In a developing roster dilemma for the Boston Red Sox, concerns arise regarding the long-term roles of Masataka Yoshida and Rafael Devers. The team's expensive roster construction is contributing to this predicament, which has already had minor repercussions during the 2024 season. However, as time progresses and the team prepares for future contention, the quandary will only amplify, necessitating a difficult decision to be made.

Currently, the Red Sox have designated Yoshida solely as their designated hitter (DH) for the 2024 season. However, his inclusion in the lineup is not guaranteed and depends on other variables. Last week, Yoshida missed out on starting for five consecutive games, spanning different cities and opponents. Not only was he not allowed to play in the outfield, but he also failed to earn the starting role over Devers at third base and was not the go-to left-handed bat off the bench. The reasons behind these decisions remain unclear, leaving fans pondering multiple possibilities.

The long-term role for Yoshida on the team becomes a pressing question when considering his contract. With four more years remaining on his $18.6 million per season contract, Yoshida represents the team's third-largest payroll commitment. Additionally, the organization's reluctance to deploy him in the outfield due to perceived defensive deficiencies suggests that this decision may persist for the next few years.

The situation becomes increasingly complex when factoring in Devers. The Red Sox have invested $313 million in Devers for the next decade, making him the team's highest-paid player. It is becoming apparent that at some point, Devers will need to transition to the DH role, ideally before Yoshida's projected departure from the roster in 2028.

The conflicting long-term goals for both players raise the crucial question of how the organization plans to handle Yoshida's role on the team moving forward. If the front office intends to keep Yoshida as the DH for the next four years, it could lead to further roster issues in the future. Such choices may indicate that the Red Sox are already signaling their preference for Devers over Yoshida in the long run, albeit without verbal confirmation.

Considerations for Devers' role are vital, both for his offensive prowess and his ability to succeed long-term. As an exceptional hitter with a career OPS+ of 125, Devers consistently proves his ability to perform well in high-pressure situations. Sunday night's game against the Cubs showcased his exceptional approach at the plate, delivering a crucial hit that led to a game-winning run. Persisting with Devers in a potentially injury-prone position for the sake of fielding might jeopardize his offensive productivity in the later years of his contract.

Drawing a parallel from history, the transition of Devers to DH could follow the path of Edgar Martinez, who played 552 games at third base before permanently moving to the DH role. Martinez's offensive numbers improved significantly when he became a full-time DH, highlighting the potential benefits for Devers if he were to adopt a similar transition.

While the front office may have missed an opportunity to trade Yoshida last offseason, the looming scenario in 2025 presents a potential resolution to this roster conundrum. As infield prospects like Trevor Story, Vaughn Grissom, Marcelo Mayer, Ceddanne Rafaela, Chase Meidroth, and Nick Yorke vie for playing time in the future, the Red Sox may be compelled to make a difficult decision and part ways with Yoshida.

As the 2024 season unfolds, uncertainties regarding Devers' durability and the team's handling of Yoshida remain unanswered. Speculations persist as to whether both players will make the next Red Sox playoff roster or whether one or neither will be included. The future holds a challenging decision for the Red Sox organization, as they strive to maintain the team's competitiveness while ensuring the long-term success of key players.