When former Boston Red Sox third baseman Alex Bregman signed a five-year, $175-million deal with the Chicago Cubs last offseason, one reported sticking point between Bregman and the Red Sox that led to the All-Star leaving was an organizational policy against no-trade clauses. As the Red Sox head into the offseason with a massive need for power in the lineup, could that policy cost them again? 

While the offseason has yet to officially begin, the Red Sox have been linked twice to one of the top free-agent bats, soon-to-be former Seattle Mariners outfielder Randy Arozarena, by Mariners beat reporter Ryan Divish of the Seattle Times. 

In Divish's latest reporting on Arozarena's impending free agency, he reiterated that the 31-year-old would prefer to stay on the East Coast and join a team that holds its spring training in Florida, where he spends the offseason, citing the Red Sox, Yankees, Mets and Phillies as possible options that fit that criteria. 

As for the terms that Arozarena and agent Scott Boars might be looking for? According to Divish, the soon-to-be free agent could target a five-year, $110-$120 million deal after a career year in 2026 and will "almost certainly be looking for full no-trade protection." 

Full no-trade clauses and similar trade protections certainly limit roster building and, in the Red Sox' case, prevent the use of prospect capital to get out from under bad deals, which most free-agent contracts end up being. 

That said, as teams shift away from the 10-12 year mega contracts that top free-agent bats were signing in years past, it becomes easier to wait out the bad deals, like Boston has done with shortstop Trevor Story, who signed a six-year, $140-million deal with the team ahead of the 2022 season, that has not gone according to plan. 

Regardless, if you are pursuing a player like Arozarena, or Bregman before him, you believe they'll be a franchise cornerstone in the immediate future. If the discussions break down over no-trade clauses in five- or six-year deals, then you'd have to seriously consider how competitive the team is going to be during the "prime years" of the deal. 

Ultimately, only time will tell whether the Red Sox have learned from last offseason's mistakes as they look to build a team truly capable of contending for the World Series. 

With the Red Sox officially in offseason mode, Zach Coe and David Azer are back on the 'Entering Kenmore' Podcast discussing how close Boston is to winning a World Series, offseason needs, and whether or not the 2026 season was successful. Check it out wherever you get your podcasts, or in the YouTube player below: