The Chicago Cubs have a problem as they head into the 2026 season, but it’s definitely a good problem to have. They need to find every day playing time for five quality infielders when there’s only space for four.
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The signing of free agent third baseman Alex Bregman pushed the still-developing Matt Shaw from his hot corner spot and forced some shuffling of plans. As of right now, the Cubs will be using the 24-year-old Shaw in a super utility role, as a backup at second base, third base, and corner outfield.
But those plans could change.
A desperate Boston Red Sox trade partner
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The Boston Red Sox, since unexpectedly losing Bregman to the Cubs, appears to be a team burning to save face. Despite signing free agent pitcher Ranger Suarez to a 5-year contract days after the Cubs-Bregman deal was announced, they have looked to be flailing in attempts to fortify their roster, especially with a thinned-out infield that has holes at both third base and second base.
Third baseman Eugenio Suarez and second baseman Brendan Donovan, both reported targets of the Red Sox, have come off the market in recent days. Suarez signed a one-year, $15 million deal with the Cincinnati Reds and Donovan was traded from the St. Louis Cardinals to the Seattle Mariners. Meanwhile, free agent Luis Arraez, a former second baseman converted to a first baseman, was signed to a one-year, $12 million deal by the San Francisco Giants and given the team’s full-time second base gig. Even supposed talks with the Arizona Diamondbacks and Houston Astros for second baseman Ketel Marte and third baseman Isaac Paredes, respectively, have reportedly hit a dead end.
Amid talks of converting outfielders to infielders, Boston is still looking for every day infield help. They’ve run out of quality free agent targets. And they appear to be down to one last possible trade partner– the Cubs.
By all accounts, Chicago has been willing to listen to offers for second baseman Nico Hoerner and Shaw, but is not all that motivated to trade either. Hoerner will become a free agent at the end of the 2026 season, but he’s become a team leader and figures to play an important role in the 2026 squad’s postseason push. Shaw, meanwhile, showed enough promise in his rookie 2025 campaign that the team sees him as not only insurance against a starter’s injury in the coming season, but also as insurance at second base in case they can’t re-sign Hoerner.
Matt Shaw would be the most likely target
Of the two tradeable assets, though, Shaw is probably much more likely to be dealt.
Per ESPN’s Jeff Passan:
“I’d be surprised to see Nico Hoerner move at this point. Dealing Matt Shaw is complicated because the Cubs believe there’s more than he showed last season, but teams are valuing him closer to the guy he was than the guy he might be. As of right now, both stay put, but we can’t discount that other moves made by other teams compel potential trade partners to re-engage and up their offers.”
But what if Boston really, really wants the Massachusetts native Shaw?
What the Red Sox have to offer
They have some very attractive young pitching in their organization. Especially, lefties Payton Tolle and Connelly Early, ranked no. 17 and no. 52, respectively, in Baseball America’s list of top 100 prospects. Both 23-year-olds are said to be major league-ready right now.
The Red Sox would surely prefer not to trade either, but desperate times could make for desperate measures. And with two team-controlled years of offseason trade acquisition Sonny Gray and five years of Ranger Suarez ahead of them, the starting rotation might not be of immediate pressing concern.
The Cubs might be moved from their trade indifference if such a top pitching prospect were dangled in front of them. Matthew Boyd, Jameson Taillon, and Shota Imanaga could all possibly be leaving via free agency at the end of next season, so the need for arms will be there. And if the arms can be affordable and team-controlled for the next 5-6 years, all the better.
Realistically, the big haul would probably come for Shaw rather than for just one year of Hoerner. But, again, Chicago does seem to have a concrete plan for the future of their former no. 1 draft pick.
However, the Red Sox may be motivated to sacrifice a lot for what they need in the here and now. A recent Sports Illustrated trade proposal has Shaw going for Early and RHP prospect Juan Valera (no. 11 in the organization). If that deal is put out there, it’s hard to see the Cubs turning it down.
Starting pitcher could fall into Chicago Cubs laps
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