A Red Sox Elly De La Cruz Trade Was Discussed At The Deadline. Will It Happen This Winter?

red sox elly de la cruz

August 10, 2026

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The Major League Baseball (MLB) trade deadline has come and gone, and the Boston Red Sox made headlines by acquiring arguably the best hitter that swaped teams in Adley Rutschman. According to USA Today baseball insider Bob Nightengale, they had actually tried to reel in a bigger fish and failed, at least temporarily. A Red Sox Elly De La Cruz trade was discussed with the Cincinnati Reds.

The talks didn’t get far, and there are no reports about a potential package that was offered, but it’s safe to assume it would have been bigger than what the Baltimore Orioles got for their injured catcher (Anthony Eyanson, Carlos Navarez, Kyson Witherspoon, and Enddy Escobar). A deal for De La Cruz would’ve been headlined by the team’s top prospect, Franklin Arias, who is also a shortstop.

A Red Sox Elly De La Cruz Trade Could Still Happen

Even though the wheeling and dealing of the baseball season is essentially over, the initial discussions could have laid the groundwork for a deal in the offseason. This would be similar to the move Craig Breslow made in 2024, when Boston kicked the tires on Chicago White Sox pitcher Garrett Crochet at the trade deadline, and then swung a deal for the lefty in December. The team followed up the trade by signing Crochet to a six-year deal worth $170 million.

De La Cruz would likely demand a large extension after a trade as well, since he is under team control through the 2029 season. He did turn down a deal from Cincinnati that would have been bigger than Joey Votto’s 10-year contract for $225 million. Maybe that’s because he is thinking $22.5 million per year is a pittance compared to Manny Machado’s $30 million per year with the San Diego Padres.

Maybe the Reds All-Star declined the deal because he doesn’t want to spend the next decade on a losing team. Loyalty is great, but it hasn’t panned out for Mike Trout in Anaheim. Either way, the Red Sox can satisfy both concerns for De La Cruz. They are a perennial playoff contender, and the ownership group has deep pockets it’s willing to empty for the right player.

Could A Lockout Kill The Deal?

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An incredibly large hurdle that needs to be cleared before a deal like this can go down is the league’s Collective Bargaining Agreement (CBA). It’s up at the end of the year, and the owners are pushing for a salary cap, similar to the one in the NHL. They are offering the players a $2 billion pay raise to accept one, but it appears there is going to be a fight and a work stoppage before an agreement can be reached.

How would a work stoppage kill the deal? In sales, there is a saying that “time kills all deals”. The longer either party has to marinate in the idea of a swap, the more likely that marinade is going to sour. Even if a stoppage is brief and the players come to their senses, taking the pay bump, that would mean a salary cap in the vicinity of $245.3 million.

The Red Sox payroll, if all options are picked up for 2027, would be $266.9 million. They couldn’t add $30 million to that; they’d need to cut roughly $20 million. So, even if the two teams were to agree on a trade, the deal would fall through because Boston couldn’t offer a lucrative extension. In a dream world, they’d figure a way to dump Trevor Story’s $25 million salary, but no team is taking that on.

A deal could be made if Boston chooses to copycat the Los Angeles Dodgers and give De La Cruz a large deferred salary. This would also require the shortstop to accept something like $5 million per year for five years, the next five years at $40 million per year, and then five years after the deal is over, De La Cruz would get $35 million per year. It would be a 10-year contract for $400 million, but structured to fit the cap.

This would also assume that deferred contracts aren’t also on the chopping block in the new CBA. The Dodgers have made quite a few enemies in both ownership and the players’ unions with their tactics. For now, it’s a pipe dream, but what a beautiful dream it is for Boston fans. The idea of De La Cruz playing in the middle of their infield for the next decade.

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