Cubs Could Get Second Chance at Alex Bregman at Trade Deadline

The Chicago Cubs are among the best teams in Major League Baseball, though it’s hard not to think what could have been had their offseason pursuit of now Boston Red Sox third basemen Alex Bregman had been successful.

All winter long, the never-ending sweepstakes for the former Houston Astros perennial All-Star dominated the headlines, and though the Cubs made an admirable run, they were not able to lock him down.

More News: Pete Crow-Armstrong on Pace to Join Elite Group in Cubs History

As Chicago has hit a little bit of a skid and the third base position for the team as a whole sits dead last in Major League Baseball with an OPS of just .544, wondering what Bregman could have done to this lineup is understandable.

However, even though Boston gave Bregman a megadeal which is set to pay him $40 million per year for three years and contains opt outs in each season, they could be willing to trade away the slugger.

More News: Previous Cubs Deadline Acquisition Gets DFA’d by Division Rivals

The Red Sox shocked everyone last week when they traded Rafael Devers to the San Francisco Giants. With the season not going according to plan as well as the fact that Bregman has the looming opt out that he is likely to exercise this winter, trading him is not the craziest idea.

Jeff Passan of ESPN named the top-50 players who could be traded at the deadline, and Bregman of course came in at No. 1. Though Passan only gives it a 10 percent chance that Boston would actually trade him, he named the Cubs as the top fit if it were to happen.

More News: Cubs Insider Expects Team To Land a Starting Pitcher in Next Two Weeks

Young rookie Matt Shaw seemed to be putting it together after returning from his demotion, but he has started to struggle again at the plate over the last month.

A real case can be made that Chicago is not in a position where they can be giving away at-bats in the name of development if they are actually going to contend for a title.

More News: Cubs Calling Up Former All-Star Pitcher From Triple-A After Impressive Showing

Someone like Bregman, who would likely only be a one-year rental, could be the perfect balance between giving the Cubs an elite third baseman and not blocking the position from Shaw for the foreseeable future.

If Boston does start fielding trade offers for Bregman, Chicago absolutely should be at the forefront of the negotiations and be aggressive enough to the point where they can land him.

The Red Sox are not likely to want to deal him, but if they are and the price is at least somewhat reasonable, the Cubs simply must do whatever it takes to make it happen.

For more Cubs news, head over to Cubs On SI.

Related Posts

🚨BREAKING NEWS: YANKEES, CARLOS LAGRANGE BLASTED BY CUBS IN ARIZONA EXHIBITION! In a disappointing exhibition game, the Yankees and Carlos Lagrange were overpowered by the Cubs in Arizona. The dominant performance by the Cubs has left the Yankees and their star player with plenty to work on as they prepare for the season ahead.

Yankees’ Spring Finale Ends in Blowout Loss to Cubs, Carlos Lagrange Struggles on the Mound MESA, AZ — March 23, 2026 — The New York Yankees wrapped…

🚨 BOMBSHELL: Mets Trade Prediction Sends Astros’ $60 Million Slugger for Mark Vientos! The shocking swap could shake up the entire MLB landscape as teams gear up for a blockbuster season. Is this the bold move the Mets need? ll 👇👇👇

New York Mets Eye Big Trade with Houston Astros: Christian Walker Set to Join Queens in Blockbuster Move As the New York Mets gear up for the…

🚨 EXCLUSIVE: “Jerry Jones Cares a Lot”: PFF Mock Draft Has Dallas Cowboys SHOCKINGLY TRADING UP to Select RB Jeremiyah Love! Fans are stunned as the franchise makes a bold move that could change their offensive future. Will this gamble pay off? ll 👇👇👇

The Dallas Cowboys have the 12th and 20th overall selections in the 2026 NFL Draft. There are a lot of holes on Dallas’s roster that need to…

ASTROS JUST LANDED A MONSTER UPGRADE! Their Blockbuster Trade Acquisition Has Officially Locked Down the #2 Spot in the Rotation — Houston’s Starting Staff Is About to Become an Absolute DEATH TRAP for Every Lineup in the AL!

  Houston Astros starting pitcher Mike Burrows (50) delivers a pitch during spring training. | Sam Navarro-Imagn Images The Houston Astros might have lost a big piece…

🚨 BOMBSHELL: Dodgers CRUSHED Rival with a $69 Million Move! The unexpected deal shakes the competition to its core, leaving fans stunned and rivals scrambling. Is this the game-changing move that defines their season? ll 👇👇👇

The Dodgers’ Bold Move: How Edwin Diaz’s Departure from the Mets Strengthens L.A. and Adds Fuel to the NL Rivalry The New York Mets might not have…

GIANTS DROP THE GAUNTLET! Official Starting Pitchers Locked In for Massive Season-Opening Clash vs. New York Yankees — This Rotation Reveal Is About to IGNITE the Subway Series Rivalry Like Never Before!

San Francisco Giants pitcher Robbie Ray. | Rick Scuteri-Imagn Images The obvious was known — Logan Webb will start for the San Francisco Giants on opening day…