The Boston Red Sox have maintained a winning record this season, despite the front office’s struggles to balance fan expectations and a soft rebuild strategy.
As the trade Begings the front office should stop trying to juggle fan expectations with their strategic realities. They should consider trading Tyler O’Neill, Kenley Jansen, and Nick Pivetta—three players on expiring “rental” contracts earning a total of $29.3 million this season—and focus on building a brighter future, even if it means publicly admitting that contention this year is unlikely.
Caught Between Competing Interests
Boston Red Sox executives have been stuck between rebuilding around young, inexpensive talent and meeting fan expectations for World Series contention every year.
This balancing act began when Red Sox CEO Sam Kennedy and chief of baseball operations Craig Breslow faced jeers at a team event in January, where fans and star player Rafael Devers had hoped for more significant offseason additions. Earlier this month, Kennedy claimed the team had “under-performed,” a statement he later retracted as fans felt the team was not in a position to win. In a recent interview with the Financial Times, team owner John Henry estimated the team had “one in 20 or one in 30” odds of winning a championship, a sentiment that did not sit well with the players.
Recently, Breslow tried to navigate the upcoming trade deadline delicately in an interview with The Athletic. “I don’t know that it makes sense to say anything is off the table or anything is off-limits,” he said, emphasizing a balance between competing interests to do what’s best for the organization.
The “competing interests” pit fans and players against team executives, a common scenario in professional sports. However, the 2024 Red Sox have yet to fully commit to either direction and continue to falter publicly. The trade deadline is a crucial opportunity to flip pending free agents for future prospects and commit to an inevitable rebuild.
These Leases Are Already Up
O’Neill, on a one-year, $5.85 million contract, has started the season strong and offers a powerful outfield bat for interested teams. Jansen, earning $16 million in the second year of a two-year, $32 million contract, is a veteran arm that can bolster a playoff-bound bullpen. Pivetta, with a $7.5 million single-year contract, can provide valuable innings for teams with strong starting rotations.
Despite their individual successes, this trio has not been enough to push the Red Sox into a Wild Card spot. It’s unlikely they will lead the team to significant postseason success, and their future with the Red Sox beyond this season is uncertain.
“After a strong start to the year, the Red Sox have been playing sub-.500 baseball since the beginning of May, and while it has still been enough to stay relevant in the Wild-Card standings, it might be difficult to justify buying,” as Joel Reuter of Bleacher Report noted. “It’s unlikely they will shop any controllable pieces, but rentals like Tyler O’Neill, Nick Pivetta, and Kenley Jansen could be on the move.”
The Red Sox have underperformed their $181 million payroll, the 11th-highest in MLB this season, partly due to injuries, highlighting the need for a strategic shift. For 2025, the team has $107 million committed, the 16th-highest mark currently. Whether the front office will use this flexibility to make win-now additions next season remains to be seen, but it may compel executives to embrace a rebuild, regardless of other interests.
