Will the Boston Red Sox cut ties with Aroldis Chapman before the 2026 Major League Baseball trade deadline?

That’s going to be the biggest question hanging over the organization ahead of the deadline if the Red Sox aren’t able to fully turn their season around. After taking down the New York Yankees on Friday, Boston has a 27-35 record. The Red Sox’s contest against the Yankees was postponed on Saturday and the two American League East rivals will conclude their brief series at Yankee Stadium on Sunday.

Boston clearly has a lot of work to do right now. With the club currently struggling in the standings, USA Today’s Bob Nightengale wrote that Chapman is “expected” to join his eighth different team this summer and get moved.

What Will Boston Do With Aroldis Chapman?

“Boston Red Sox closer Aroldis Chapman is expected to join his eighth different team, and potentially be in the postseason with his sixth different team,” Nightengale wrote. “He is the top reliever available on every contender’s target list, converting 28 consecutive saves dating back to last season, one shy of his career record.”

If the Red Sox are eight games below .500 at the beginning of August, like they are now, then this idea unfortunately, would make sense. But it’s important to note that on Saturday, The Athletic’s Jen McCaffrey reported that Boston has fielded calls on Chapman, Justin Slaten, and Garrett Whitlock but has told teams that the trio currently isn’t available. The idea of Chapman being moved is fully contingent on whether the Red Sox can make progress in the standings over the next two months.

Right now, the Red Sox are just three games out of an American League Wild Card spot, so it’s not the craziest idea in the world to believe they can make up some ground here. Plus, let’s not forget that some point Garrett Crochet and Roman Anthony will be able to return.

So, right now, the Red Sox are in a tough spot, which gives some life to Nightengale’s point, but it’s still a bit too early to fully jump to conclusions. If the Red Sox can go on a little run, then all of a sudden the perception will shift around Boston. If not, then the club will end up getting a haul in exchange for Chapman if the club actually does end up moving him before the deadline.

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Giannis Antetokounmpo’s trade rumors seem to evolve weekly, but two teams have been linked to the former NBA champion and league MVP more than any others: the Boston Celtics and Miami Heat.

Since trade rumors initially picked up early in the offseason, it’s believed that Antetokounmpo’s preferred trade destination is a title contender in the Eastern Conference. Outside of the obvious Knicks, who are up 2-0 in the NBA Finals, there are a handful of teams that fit that bill: Detroit, Cleveland, Philadelphia, and Orlando could be considered in that tier of Eastern Conference teams.

However, most teams that have the assets to trade for Antetokounmpo would need to gut the better parts of their lineup in order to make a legal trade happen, and that would make them less likely to be contenders.

That’s the advantage Boston seemingly possesses over just about every other team Antetokounmpo would be willing to play for: its roster would not be depleted in the process of acquiring the ‘Greek Freak’.

Speaking on the Dan Patrick Show, The Athletic’s Sam Amick said the rumors of Antetokounmpo to the Celtics have some serious traction, at least on Antetokounmpo’s end.

“Miami is the loudest noise, you continue to hear that … yes, it appears everybody you talk to says Miami at the deadline had a deal that was close,” Amick said. “So the noise is tied to Miami, but there’s also some understanding that Giannis has questions about what that Miami roster would look like on the other side of the deal.

“I think the Celtics are a pretty intriguing option in terms of being competitive,” Amick added. “This is something we’ve heard from Giannis’s side that the intrigue is real. The respect for Joe Mazzulla, the way that he might see that roster. Do I think it changes things? I don’t know yet. But I think it’s worth watching.”

The seemingly obvious piece for Boston to send back, whether to the Bucks or a third involved team, is Jaylen Brown. Brown has a similar contract to Antetokounmpo’s, and is a quality enough player that he could be the only player the Celtics trade away in the deal, giving them plenty of runway to compete for a championship in the aftermath.

So, from a salary cap-balancing perspective, the trade could be done easily. But Boston will have other factors to consider. Does the fit with Antetokounmpo and Jayson Tatum together make sense and will it lead to a better title shot? And, even if Brad Stevens thinks it is, does it make sense to trade away your longest tenured player who has already proven he can win a championship alongside Tatum.

Brown’s name has been dangled in a few different rumored trade scenarios over the last few offseasons, but no other occasion has had this much traction behind it.

And for the Bucks, trading Antetokounmpo appears to be a near-certainty at this juncture.

“It seems very likely … it’s not often you have an owner publicly framing the timeline, and that’s what Jimmy Haslem did. We just saw Jimmy Haslem do a blockbuster trade with Myles Garrett in the NFL, showing he’s certainly ready to pull that trigger if he needs to. I do expect it to happen.”

So the Heat and Celtics, who have built quite a fierce rivalry in the 21st century, and especially with their recent playoff clashes, will be pitted against each other once more. This time, Antetokounmpo is up for grabs.

Stevens entered the offseason saying he’d do everything in his power to make Boston a more competitive team and bring them another championship. He also said he’d take a dunk over a 3-pointer on every possession if he could. If he lands Antetokounmpo, he just might get both his wishes.

The Boston Red Sox are currently resisting becoming significant sellers in the trade market. At the moment, Boston sits last in the American League East at eight games under .500. Despite entering 2026 with high hopes, the club has struggled mightily during the first half of the season. Because of this, many believe that the Red Sox will make some significant moves this summer.

Nevertheless, WEEI’s Rob Bradford is now reporting that Boston officials are rebuffing outside interest in three key relief pitchers. According to Bradford, teams asking about the possible availability of Aroldis Chapman, Garrett Whitlock, and Justin Slaten are being turned away. The reporter, however, specifically claims that the club is rejecting potential offers as of right now.

The situation regarding the trio could certainly change in the near future. Assuming the Red Sox continue to falter, team officials may eventually opt to offload the standout relievers. So far this season, Chapman, Whitlock, and Slaten have been three of the team’s top pitchers in their bullpen. Chapman has allowed one earned run all season, while Whitlock and Slaten have provided stability working ahead of the closer.

Whitlock has been out of action since landing on the injured list on May 28 with knee inflammation. The reliever is expected to return to Boston’s bullpen in the coming days, though. Chapman is also dealing with an injury issue. Red Sox manager Chad Tracy confirmed on June 5 that the closer is enduring a “minor hamstring” problem. So far, Chapman has avoided the IL.

Boston Red Sox Eyeing Other Deals as Chapman, Whitlock, and Slaten are Off Limits

GettyAroldis Chapman would receive plenty of interest if the Boston Red Sox opt to trade him.

While the Boston Red Sox are holding on to their top relievers for now, they are willing to offload Connor Wong. According to The Athletic’s Jen McCaffrey, team officials are gauging interest in the backup catcher. The veteran backstop is available for trade because Boston has three catchers on the roster. Along with Wong, the Red Sox also have Carlos Narvaez and Mickey Gasper at the position. McCaffrey believes that Boston prefers to keep Gasper over Wong.

The Red Sox, however, are also being linked with making a key addition to the roster. ESPN’s Buster Olney recently claimed that Boston is specifically looking to acquire a right-handed hitter. With Trevor Story and Caleb Durbin struggling, Willson Contreras and Ceddanne Rafaela are currently the club’s two most prominent righties in the lineup. Not only are the Red Sox eyeing a new bat, but they are willing to spend significant money to do so.

Boston Likely to Become Sellers if Struggles Continue

Boston Red Sox chief baseball officer Craig Breslow has admitted that the club is being patient in the trade market. According to Breslow, it is just too early in the season to really commit to being a buyer or seller. The exec also claimed that while he is having “a lot of conversations” with other teams, he still believes that his current roster can turn things around.

Nevertheless, the situation can change fairly rapidly if Boston does not start to improve quickly. The Red Sox are already 11 games back in the division and have to jump six other teams to be in a wild card place. Boston will try to get a win streak going when they face the New York Yankees on Saturday, June 6.

Christopher Moore Christopher Moore has been a Heavy.com contributor since 2025. With over a decade of experience in the industry, he has published thousands of articles reporting on multiple professional sports. He was previously a sports writer for World Soccer Talk, the Yahoo! Contributor Network, and the Maryland Sports Blog. More about Christopher Moore