The Boston Red Sox are confronting a critical choice involving Alex Bregman‘s contract as the trade deadline approaches. After signing a three-year, $120 million deal this offseason, Bregman holds an opt-out option following the current season, raising urgent questions about whether to negotiate an extension or consider trading him to avoid losing him in free agency.

With the team struggling to keep pace in the postseason race, speculation has intensified about Bregman’s future. Boston’s front office, led by chief baseball officer Craig Breslow, must evaluate the benefits of securing Bregman for the long term versus acquiring future assets that could strengthen their roster if a contract extension remains elusive.

Expert Views on Red Sox’s Approach to Bregman’s Contract Situation

Former Minnesota Twins player Trevor Plouffe recently discussed Bregman’s situation during an episode of Baseball Today, offering insights into the strategic decisions facing the Red Sox. Plouffe emphasized the dilemma caused by Bregman’s opt-out and his representation by agent Scott Boras.

“Alex Bregman is a guy that I think fits the Red Sox very, very well. But he’s got an opt-out at the end of the season,” Plouffe said (from 8:51). “He’s got Scott Boras as his agent, and I know they’re trying to get an extension done with him before the deadline. And if they do that—great. These two teams can live happily, you know, for the next couple of years together. But if you can’t get one done, I would look to get Bregman somewhere else.

“I think you can get a pretty nice haul. I think you can get a nice reliever for him to put in the back end of your bullpen. That’s kind of where I would be looking … Bregman’s the one that I would be like, ‘Okay, well, if we can’t get a deal done here, we’ve got some guys that can cover the infield, and you can get a pretty good return for him.’ So that’s where I’d be looking.”

Plouffe’s assessment suggests that negotiating an extension is the best course of action, but if that falls through, Cleveland should actively pursue offers to trade Bregman for valuable bullpen support and infield depth.

Potential Landing Spots for Alex Bregman If Traded

The conversation continued with Plouffe identifying possible destinations for Bregman should the Red Sox decide to trade him. While some teams pursued him during free agency, not all are considered likely trade partners now.

Plouffe dismissed the Detroit Tigers as a probable option, noting that their third base spot is currently stable with prospect Matt McKinstry. Instead, he highlighted the Seattle Mariners as a feasible landing place, especially since they possess bullpen arms that could appeal to Boston in a potential exchange.

“I don’t know if Detroit’s willing to trade for him right now,” Plouffe added. “I mean, McKinstry’s kind of settled in over there at third base. The Mariners are somebody that I could see trading for him. And they have some back-end-of-the-bullpen guys that I think they’d be willing to swap out.”

The ongoing discussions also jokingly touched on the unlikely possibility of a trade involving the New York Yankees, given their need for a third baseman at the deadline, but such a move remains speculative.

Implications for the Red Sox and Alex Bregman’s Future

The Red Sox’s decision about Alex Bregman could significantly influence their competitiveness in the postseason and beyond. Extending the star third baseman would secure a cornerstone player, whereas trading him might offer immediate improvements in weaker roster areas, particularly the bullpen.

With the trade deadline approaching, Craig Breslow must weigh these options carefully. The outcome will shape Boston’s trajectory this season and impact their strategy heading into free agency, underscoring the urgency and complexity surrounding Bregman’s contract.