The Chicago Cubs exited the MLB Winter Meetings with clear intentions but unfinished business. If they want to legitimately contend in 2025, there is one blockbuster move that stands above the rest: swing a deal with the Boston Red Sox for outfielder Jarren Duran.
This is the type of aggressive, upside-heavy move that transforms a solid roster into a dangerous October threat. It also aligns perfectly with the Cubs’ current competitive window and prospect capital.
Why Jarren Duran Is the Ideal Post-Meetings Target
From a roster-construction standpoint, the Cubs need an impact bat who can lengthen the lineup and change the game with speed and energy. Duran checks every one of those boxes while still fitting the age and control timeline of a club that wants to win now without emptying its entire farm system.
Chicago’s lineup has often lacked a true dynamic presence at the top, someone who can pressure defenses, turn singles into doubles, and change the tone of a series. Adding a player like Duran immediately alters how opposing pitchers attack the Cubs from the first pitch of every game.
There is also a strategic urgency here. The rest of the National League is not standing still, and the Cubs cannot rely solely on internal growth to keep pace. A bold trade sends the message that the front office is committed to maximizing the current core while still keeping an eye on the long-term structure of the roster.
Duran gives the Cubs flexibility both defensively and in the lineup, creating natural fits around existing pieces rather than forcing awkward position changes. The move would also allow the Cubs to better withstand injuries or underperformance in the outfield group without sacrificing production.
Financially, this type of acquisition is more attractive than splurging recklessly in free agency. Instead of committing massive long-term dollars and dealing with aging-curve risk, the Cubs would be using prospect capital to obtain a player who still fits into a sustainable payroll model.
The cost will not be cheap, but that is the reality of acquiring a high-impact, controllable piece from another big-market club. For the Cubs, this is precisely the kind of moment when you lean into your player-development strength and use it as currency.
The Perfect Blockbuster Trade Cubs Must Make
To get this done, the Cubs will need to structure an offer that appeals to Boston’s desire to add upside and depth while respecting the value of a proven big-league contributor. The Red Sox are looking to thread the needle between competing and retooling, and a package headlined by high-ceiling talent is the type of proposal that makes them listen.
Chicago has the prospect depth to make this work without dismantling its entire pipeline. The key is finding the right balance between headliner talent and supplementary pieces that give Boston both immediate and future value.
Here is the ideal blockbuster framework the Cubs should pursue to land Jarren Duran from the Red Sox:
Cubs receive:
- OF Jarren Duran
Red Sox receive:
- OF Kevin Alcántara
- RHP Brandon Birdsell
From the Cubs’ perspective, this deal is aggressive but justifiable. They are moving a premium outfield prospect and a pitching piece to secure an established difference-maker who can help them win right now.
For the Red Sox, this trade replenishes impact upside in the outfield pipeline while adding an arm with intrigue and developmental runway. It fits an organizational direction that needs more controllable talent without fully punting on the near term.
The reason this is the “one” blockbuster the Cubs must make is simple: it checks every strategic box. It upgrades the major-league roster immediately, aligns with the competitive window, leverages organizational strengths, and does so without dipping into draft capital or overextending financially.
In a post-Winter Meetings landscape where impact opportunities are disappearing quickly, standing pat is the real risk for Chicago. Moving decisively for Jarren Duran is the type of statement move that signals the Cubs are serious about climbing back into the top tier of the National League.
