Red Sox Nightmare Scenario has Rival Executive ‘Laughing’

Alarm bells have been ringing across Red Sox Nation since the regular season began. But they may be louder than ever right now. 

A popular pick to emerge as American League East champion in 2025, Boston limped out to a 1-4 start that was negatively accentuated by Rafael Devers’ historic slump to open the season, going 0-for-21 with 15 strikeouts. And that was just the start of a bumpy ride for the Red Sox throughout the first half of the season. 

A pitching staff that was riddled by injuries and inconsistent outings; a top prospect in Roman Anthony whose delayed debut befuddled the team’s followers; and of course, the Devers trade that shocked the industry. But recent reports could be the straw that breaks the fan base’s back. 

Alex Bregman Could be Traded if Extension Not Reached Before July 31 Deadline

In a Monday column for The Athletic highlighting “10 midsummer takeaways” from around the league, MLB insider Jayson Stark suggested that Boston third baseman Alex Bregman “almost certainly will” choose to opt out of his current contract with the team. Signed to a three-year, $120 million deal at the start of spring training, Bregman, despite missing six weeks with a quad strain, has put together an All-Star season that Stark wrote has put Bregman “in prime position to cash in.” 

Then on Tuesday, in a separate piece for The Athletic answering reader questions, former GM Jim Bowden touched on the complications surrounding Boston’s efforts to sign Bregman to an extension, particularly with Scott Boras serving as Bregman’s agent. But in a real punch to the gut for Red Sox fans, Bowden warned of what might happen if an agreement is not reached before the July 31 trade deadline. 

“I’m hearing, in my conversations throughout the league, if he’s not extended, they could end up trading him to Seattle, Detroit or Milwaukee,” Bowden wrote. 

And, citing the reaction from a rival AL executive, Stark emphasized that given the PR disaster of a season that it has been for the Red Sox, Bregman and Boras have Boston between an extremely large rock and an incredibly hard place. 

“I’ve been laughing about this for two weeks,” Stark quoted the unnamed executive as saying, “just thinking about Scott Boras’ reaction to the Devers trade with Bregman, because you know he’s sitting there thinking: ‘Just give me a blank check, because whatever I want, you guys are going to have to pay me.’” 

For a Red Sox team that has had more last-place divisional finishes (three) than playoff berths (one) since winning the 2018 World Series, the prospect of having just one season with Bregman – whose arrival, through no fault of his own, kickstarted the souring relationship and eventual breakup between Devers and Boston – would put the cap on a season of organizational dysfunction. 

Alex Bregman Ready to Return From Injury Amid Reports Over Uncertain Future

Bregman’s presence was supposed to stabilize the lineup. Before going on the injured list May 24, the 31-year-old was slashing .299/.385/.553 with 11 home runs and 35 RBIs in 51 games, providing an everyday threat in the heart of the order. 

Bregman could be back in action before the All-Star break, with the possibility that he would be inserted right into the Red Sox lineup without going through a rehab assignment. Although he has never returned from an IL stint without first playing in some minor league games, Bregman told reporters on Monday that he doesn’t think it would be an issue. 

“My leg feels really good and I swung the bat really well today,” said Bregman. “I don’t know, I feel like I can do it…I’m feeling really good. The rehab has gone amazing. I’m super thankful for our training staff, rehab staff and strength and conditioning staff I’ve been working with. Hopefully, I’ll be back playing in uniform here pretty soon.” 

As for what uniform Bregman could be wearing in August, there are plenty of playoff hopefuls with a need at third base and the prospects to trade. Seattle in particular has been floated as a prime suitor if Boston waves the white flag, with The Sporting News reporting that “the Mariners seem like they have a very real chance of ending up with Bregman.” 

The Red Sox could hang onto Bregman for the final months of the season, then let him walk and recoup a compensatory draft pick, although that feels like the least possible scenario. They could trade him now, recoup some value, and punt on 2025, which wouldn’t exactly play well in the stands or the clubhouse. 

Or they can meet Boras at the negotiating table, hold their noses, and pay Bregman as if he’s the centerpiece of the franchise for the next five or six years. 

One way or another, the clock is ticking. The trade deadline is just three weeks away. Bregman, if healthy, will soon be back in the lineup. And Scott Boras, as always, knows exactly how much leverage he has. 

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