The end may not quite be here yet (or Opening Day, in this case), but it’s definitely on the horizon. The Boston Red Sox and Alex Bregman seem to be locked in a game of patience, sizing each other up from across the room.
Bregman, a two-time All-Star third baseman during his nine seasons with the Houston Astros, has yet to receive the free agency offers he originally hoped for. Boston might be his best remaining shot at clearing the $150 million mark, but the Red Sox appear content to wait, likely hoping his asking price drops.
But what if, in some way, Boston is deliberately dragging its feet because they’re aiming to lose the Bregman sweepstakes? Next winter’s free agent class features a player who could radically alter their plans: Vladimir Guerrero Jr.
Guerrero, one of the premier right-handed hitters in baseball, is coming off a strong run with the Toronto Blue Jays. At just 26 years old entering the 2026 season, he offers youth and power—two attributes that make him especially enticing to a Red Sox lineup currently lacking in right-handed power. By comparison, Bregman, who will turn 31 during most of the upcoming season, represents a more experienced, but older, option.
Recently, Jordan Llanes of ClutchPoints suggested Boston should hold off on Bregman and instead set their sights on Guerrero, who could be a game-changer for the 2026 season.
“This isn’t to say Bregman wouldn’t fit,” Llanes wrote. “It’s just that Guerrero Jr. would be the better choice. Fenway Park is a place he’s already familiar with, and his experience as a star under scrutiny would prepare him for the challenges of playing there full-time.”
While Boston’s chances of landing Bregman are uncertain even with their best pitch, Guerrero’s potential free agency could become a much larger spectacle. Reports from Bob Nightengale have already linked Boston as a likely non-Blue Jays suitor for Guerrero, but a lot can change in a year.
Spotrac projects Guerrero to command a 12-year, $427 million deal next offseason, though it’s likely he’ll aim for the $500 million range. Signing Guerrero would push the Red Sox into uncharted waters, as they’ve never inked a contract within $100 million of that lower-end projection.
And then there’s Triston Casas, Boston’s current first baseman. Even if Guerrero represents a clear upgrade, the question remains whether a lineup featuring Guerrero alone would surpass one with both Casas and Bregman.
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