The Five Biggest Free Agency Betrayals We Could See This Winter

The kind of roster turnover we see each offseason is different every year. However, there are often players jumping from one side of a rivalry to the other.

It’s not always as significant as going from the Los Angeles Dodgers to the San Francisco Giants, or the Boston Red Sox to the New York Yankees. But division and local allegiances can be challenged on the free agent market.

This offseason’s market is rife with big-name free agents that feasibly fit with a rival of their most recent employer. How likely they are to make such a betrayal remains to be seen.

But with this array of free agents, what might some of these betrayals be?

Bo Bichette to the New York Yankees or Boston Red Sox

In an alternate reality, shortstop Bo Bichette is a World Series hero for the Toronto Blue Jays. The three-run homer he hit off Dodgers superstar Shohei Ohtani could’ve gone down in Canadian sports history forever. Alas, it wasn’t enough.

The 27-year-old is a first-time free agent, and the certainty surrounding his return to the 6 is anything but. What is known, however, is that Bichette would address holes on two division rivals.

With the Yankees, shortstop Anthony Volpe has done precious little to endear himself to the fanbase. His offense has stagnated at the MLB level, with his defense taking a dramatic hit in 2025. A lot could be attributed to his torn labrum, which he’s undergone surgery to repair, but we’re three years into Volpe’s career with him looking more or less the same player.

Additionally, second baseman Jazz Chisholm Jr. is entering his final year of arbitration. While he’s given the Yankees an edge they’d been missing for years, he’s had a few instances of bizarre responses to media questions as well as some inexcusable physical and mental errors on the field. Beyond 2026, there may be an opening at second base for the Yankees as well.

As for the Red Sox, there’s an opening on the infield, full stop. While chief baseball officer Craig Breslow recently backed the incumbent Trevor Story as his team’s shortstop, his drop-off in defensive production last year can’t be ignored.

Even if Story remains at shortstop, the Red Sox aren’t guaranteed Alex Bregman’s services in 2026, nor do they have Rafael Devers to fall back on at third. They do, however, have Marcelo Mayer. Mayer played both third and second base in his MLB stint last season, but his playing one would create a hole at the other.

Alex Bregman to the Toronto Blue Jays

After one year in Boston, Bregman is testing the free agent waters again.

One thing he mentioned in his introductory press conference in spring training, repeatedly, was how he’s never really lost as a baseball player. Not in the sense that he’s always won titles, obviously, but he lives for, and in, the postseason.

He got a taste of it with the Red Sox but lost in the Wild Card round to the Yankees. So, he had to sit back and watch former Houston Astros teammate George Springer push the juggernaut Dodgers to the brink in the Fall Classic.

The Jays don’t necessarily need a third baseman, as Ernie Clement and Addison Barger both did a phenomenal job in October. But in the event Bichette departs, they could play Clement at second base, with Andrés Giménez at shortstop and Barger in the outfield.

Bregman would give Toronto another adult in the room, and another who’s won a title in his career. He and Springer could provide both veteran leadership and top-flight production to the lineup around superstar and franchise face Vladimir Guerrero Jr.

Dylan Cease to the San Francisco Giants

The Giants are hungry to get back to October, and they have shown that hunger through a flurry of moves the past 12 months.

One way of improving their playoff odds would be to weaken those of a division rival. While Cease is coming off of a down year, he’s the peripheral darling of this offseason.

In 2025, Cease had a 4.55 ERA and averaged just over five innings per start. His ERA climbed over a run from 2024, with regression in home run avoidance and an increase in walks. However, his strikeout numbers improved and, despite the high ERA, he ranked 16th among 52 qualifiers in FIP (3.56).

Oracle Park is a bottom-tier ballpark for home runs, ranking 27th since 2023. While it’s a top-half ballpark for other extra-base hits, the park would aid Cease in covering up his biggest flaw. The strikeouts will likely follow him wherever he goes, barring an unexpected alteration to his pitching structure, so the fit is there.

Moreover, pairing Cease with a legitimate ace-level pitcher in fellow right-hander Logan Webb would give the Giants a very dominant one-two punch.

Pete Alonso to the Philadelphia Phillies

This one is contingent on Kyle Schwarber’s departure, but there’s certainly a real scenario in which Alonso dons new pinstripes in 2026.

While Bryce Harper is a capable first baseman, he’s also three years older than Alonso. And while the recent Met is one of the worst defenders at his position in the league, he would at least provide the Phillies with a safety net to get Harper off his feet a couple of times per week.

A hitter like Schwarber is almost impossible to replace. Alonso, however, would be the ultimate consolation prize. Especially considering adding him would weaken the Mets’ lineup greatly, potentially widening the gap between these two clubs.

Citizens Bank Park is a purple state for right-handed home run hitters, but not much worse than Citi Field. It’s reasonable to assume Alonso drops off slightly in the power department going to Philadelphia, but negligibly. Adding him would give the Phillies a terrifying top third of the order as well, with Trea Turner and Harper.

Kyle Schwarber to the Atlanta Braves

Sticking in the National League East, the Braves recently found an opening at the designated hitter position. Schwarber could fill that hole.

Atlanta is a tricky team to project this winter for a few reasons. For starters, it seems catastrophic injuries come with the territory of being Brave.

Last year alone, Ronald Acuña Jr., Austin Riley, Sean Murphy, and Chris Sale missed significant time — just to name a few. So, on one hand, they’re an uber-talented roster, but is it in their best interest to continue adding veterans?

Regardless, the fit is fun to examine. Thinking about it from a lineup construction standpoint, there are few one-through-nines in MLB that could hold a candle to this one:

Now, making sure at-bats are there for the reigning National League Rookie of the Year, Drake Baldwin, should be paramount. Doing so may create some displacement within the catching position or even facilitate another move. However, one can’t deny the talent seeping through that Atlanta lineup with Schwarber in the mix.