The chase for Alex Bregman is heating up and could be a perfect New Year’s boost for any team. With the Toronto Blue Jays pushing him down their list, the Red Sox might have the perfect moment to strike. But that move would leave two key players’ futures hanging by a thread.

With the Red Sox signing Willson Contreras and in the race for Alex Bregman, both Triston Casas and Masataka Yoshida are now in danger of losing their places.

“Boston is in on him… They’re still in on Bregman,” said Steve Phillips. “And if they got Bregman and they have Contreras at first… Casas still as an option to keep or trade… Yoshida an option to keep or trade… they’re really building their team.”

Both the Blue Jays and Red Sox remain engaged on Alex Bregman as free agency unfolds. Toronto interest appears conditional, with Bregman viewed behind Kyle Tucker and Bo Bichette pursuits internally. That positioning quietly strengthens Boston, where Bregman remains a priority following his 2025 opt-out decision.

Boston already addressed first base issues by acquiring Willson Contreras in a multi-player trade with St. Louis. Contreras hit 20 home runs and drove in 80 runs during 2025 for the Cardinals. He transitioned full-time to first base, giving the Boston lineup stability and roster flexibility entering 2026.

Adding Bregman, who is projected near six years and roughly $170MM, would elevate division expectations across the AL. Especially after he posted an .822 OPS with 18 homers in 114 games last season.

Such a move reshapes the infield but clouds futures for Triston Casas and Masataka Yoshida. Casas, limited by a ruptured patellar tendon, appeared in a few 2025 games before surgery ended. Yoshida also struggled to secure consistent at-bats, despite finishing 2025 with a strong final month. Both players enter 2026 under contract, with Casas controlled through 2028, Yoshida through 2027, per the team.

If retained, opportunity still exists within a strengthened roster competing atop a demanding AL East. Casas owns three remaining options, allowing rehab or platoon paths while rebuilding value during 2026. Yoshida has carried a five-year, $90MM deal since 2022 in MLB.

In that environment, competition becomes clearer, and performance will decide who remains central for the Boston Red Sox.

Boston’s pursuit of Alex Bregman now feels less speculative and more like a front-office dare. Willson Contreras changed the tone, forcing Triston Casas and Masataka Yoshida into uncomfortable clarity. If Bregman signs, Boston stops explaining plans and starts answering the division loudly again. However, the Red Sox’s options are endless.

The Red Sox can sign a Blue Jays infielder despite the fit

Roster logic usually wins these debates, until it doesn’t. Boston has spent the winter rearranging furniture while ignoring the obvious empty wall. Sometimes the cleanest solution is the one that makes executives uncomfortable. That’s where the Blue Jays come in, and where Bo Bichette quietly becomes a very Red Sox problem worth having.

Boston entered the offseason without an offensive addition, while monitoring bats through trade and free agency. MassLive indicates interest in Bo Bichette, projected to command a contract in the 7-year, $200 million range. The infield already features Trevor Story, Marcelo Mayer, and Kristian Campbell, creating immediate positional tension.

Yet that tension frames the opportunity, as Boston weighs present production against future playing time.

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Bichette brings sustained performance, leading the American League in hits twice and averaging .311 last season. He appeared in 139 games before injury, pairing low strikeout rates with consistent opposite-field contact. Fenway Park’s dimensions could support that profile, even if home run totals remain unchanged there.

Boston can adjust defensively by shifting Bichette off shortstop, preserving bats while managing development timelines.

Boston rarely chases comfort when the numbers argue otherwise, and Bo Bichette’s case argues loudly. Trevor Story, Marcelo Mayer, and Kristian Campbell create friction, but friction has powered smarter Red Sox eras. If Boston wants offense, the Blue Jays infielder offers clarity, even when roster charts start sweating.