With the offseason planning phase officially underway, the Boston Red Sox will look to build on what was ultimately a disappointing finish in the Bronx, falling to the New York Yankees in the Wild Card round. With one of the best pitching staffs in baseball but an underwhelming offense, Boston Chief Baseball Officer Craig Breslow will likely focus on offensive additions.

However, with only three pending free agents, the Red Sox have nearly every position locked in for 2027. Improving the lineup will take real creativity from Breslow and the rest of the front office. 

The Red Sox have an incredibly well-documented outfield logjam, which, when the team was at full health, forced former manager Alex Cora and current manager Chad Tracy to shuffle through five players (Roman Anthony, Ceddanne Rafaela, Wilyer Abreu, Jarren Duran, and Masataka Yoshida) through the three outfield spots and the designated hitter.

While there's little room to add to that group without first subtracting from it, the infield also looks crowded heading into the season. Willson Contreras, Trevor Story, and Caleb Durbin remain under contract for 2027, and in the case of Durbin and Contreras, will return to starting roles. While Story is expected to be pushed by top prospect Franklin Arias for the starting shortstop position. As for second base, which was a revolving door in 2026, manager Chad Tracy told reporters at the end-of-season press conference that trade deadline addition Curtis Mead enters the offseason as the favorite to start at second on Opening Day. 

To make the pieces fit together and improve the team, Breslow will have to take a hard look at the roster and make difficult decisions about who will be part of things moving forward. 

After trading three top-10 organizational prospects to the Baltimore Orioles for Adley Rutschman ahead of the trade deadline, the Red Sox enter the offseason with a depleted prospect pool that ranks 21st in baseball. 

Given the state of the farm system, Breslow may have to make more "baseball trades," similar to the deal that sent Connelly Early to the Washington Nationals in exchange for Mead. Luckily for Breslow, the Red Sox have no shortage of one of the sport's most coveted assets: young, controllable major league players. 

The Red Sox were heavily involved in the shortstop market ahead of the trade deadline, seeking a "long-term solution" at the position. In their search for a shortstop, the team reportedly checked in on everyone from Bobby Witt Jr. and Elly De La Cruz to Zach Neto and Jeremy Pena. While Witt remains a pipe dream, could Boston tempt Cincinnati with a package around Abreu and Arias for De La Cruz, who has signaled he plans to test the market when his team control is up after the 2030 season? 

This is where Breslow's ability to evaluate his own players will loom large. Who are you most confident will take a step forward and become a great player, and who would be better used as a trade asset to acquire the star power you desperately need? 

For a big-market team like the Red Sox, the easiest way to fix your problems is to throw money at them in free agency. However, that may be increasingly difficult in an uncertain labor situation, with the possibility of a salary cap looming large, paired with a weak class of free-agent bats. 

That said, Boston still has several intriguing options, including outfielders Randy Arozarena and Seiya Suzuki and second baseman Brandon Lowe. However, their former teams will likely offer qualifying offers, meaning the Red Sox would have to pay draft-pick compensation to sign them. With a depleted farm system, the team could be wary about giving up draft picks to sign players. 

With the Red Sox officially in offseason mode, Zach Coe and David Azer are back on the 'Entering Kenmore' Podcast discussing how close Boston is to winning a World Series, offseason needs, and whether or not the 2026 season was successful. Check it out wherever you get your podcasts, or in the YouTube player below: