MLB Offseason: Biggest Names About to Hit Free Agency

Published on: November 12, 2025

Updated on: January 15, 2026

Category: Advice & Tips

MLB Offseason Biggest Names About to Hit Free Agency - Blog - Square Bettor

If the tale of the 2025 MLB season was electrifying, the World Series was, as ever, its operatic crescendo. The Los Angeles Dodgers, chasing a repeat unseen since the Yankees’ run at the turn of the millennium, found themselves on the edge—down 3-0 to the Toronto Blue Jays at the roaring Rogers Centre in Game 7, their reign nearly over. The champs had already surrendered a 2-1 series lead after winning games two and three, but even as they were staring down the barrel on enemy territory, the Dodgers refused to wilt

Enter Max Muncy. In LA’s hour of need, the veteran infielder slammed a two-run homer in the eighth to cut the deficit, before Miguel Rojas hit a home run of his own at the bottom of the ninth with the Blue Jays just one strike away from victory. Their heroics dragged the Dodgers back from the brink—culminating in an eleventh-inning classic where Will Smith’s home run pierced the Canadian night and Yoshinobu Yamamoto’s nerves of steel extinguished one last Blue Jays push.

Fresh off their second straight World Series, online betting sites now make LA the favorites to complete the first three-peat since those iconic Yankees. The latest MLB betting at Bovada currently prices the back-to-back champs as a +325 favorite to make history in 2026. Yet before the echoes of that final out faded, executives across the league, from Boston to the Bay, pivoted toward the razor-sharp stakes of the offseason. 

This winter, a slew of superstars are poised to test the free agency waters. Here are the three names currently dominating the headlines, and the favorites to land their signature ahead of the 2026 campaign. 

Kyle Tucker

When you lead a franchise like the Cubs from the brink, only to enter the market at 28, fresh off a campaign for the ages, you are not merely a free agent—you are the gravitational force of the winter. Kyle Tucker’s 2025 statistics weren’t the greatest of his career: a.266/.377/.841 slash, 22 homers, 91 runs scored, 73 RBIs, defensive metrics that put him among the majors’ elite in right field. Yet what truly catapults Tucker into the stratosphere is his timing: healthy at last, his game fully actualized, his blend of power, patience, and defensive range sharper than ever.

This is not an incremental upgrade for a team. This is franchise redefinition. It’s why the Dodgers—back for more after two crowns—are rumored to be drawing up blueprints that insert Tucker into an already star-clogged outfield. Yet the chase extends further: the Yankees, haunted by lineups that cannot match the upper-tier AL powers, thirst for Tucker as Aaron Judge’s right-handed foil; the Giants see in him the cornerstone for a new Northern California era; the Phillies ponder if his glove and bat can finally push them over the National League hump. And do not count out Toronto—the scriptwriters couldn’t resist a player of Tucker’s skills returning north for a Blue Jays encore.

Day 1 of free agency will likely see an opening salvo north of $400 million for a player entering his prime. Will it be enough? In an era when five-tool, middle-of-the-order anchors are as rare as perfect games, no price seems out of reach.

Alex Bregman

When dynasties are remembered, names like Alex Bregman are stitched into every narrative thread. At 32, his credentials gleam: a .273/.360/.822 campaign with 18 home runs and his usual arsenal of defensive acrobatics at the hot corner. His value transcends numbers—he possesses the on-base prowess, the clutch October resume (over 60 career postseason games played), and the snap leadership that turns talented clubs into trophy contenders.

Detroit, charged up by a hungry young rotation and looking to install a veteran who understands fall, is all in. But the Tigers won’t have an easy run: the Phillies, looking to push past the Braves and Dodgers in the NL, covet Bregman’s switch-hitting proficiency; Atlanta views him as a seamless salve for their own hot-corner churn.

With Houston extension talks cooled to a standstill, suitors sense blood in the water—a four-year, $120 million deal could mark the largest contract for a mid-30s infielder since the heyday of Adrián Beltre and Evan Longoria. What Bregman provides, you can’t fake or teach: he is the difference between making the playoffs and lasting in them.

Bo Bichette

For a city in mourning, even the smallest hope matters—and Bo Bichette personifies hope for Toronto, even if his future may soon wear another uniform. Returning from injury with a vengeance, he hit .311/.357/.840, piled up 18 homers and 94 RBIs, and reminded anyone watching October that his contact skills and defensive steadiness are among baseball’s rarest commodities at shortstop.

The enigma? Will the cash-strapped Blue Jays pay what it takes to keep their homegrown star a la Jose Ramirez in Cleveland, or will another franchise—awed by both talent and postseason mettle—swoop in? Detroit sees Bichette as the infield keystone for a pitching-rich contender. The Braves, desperate to stop their title window from closing, relish the thought of Bichette stabilizing their infield chaos. Yankees management, ever lurking, knows he could be their next Captain in pinstripes. Dodgers, Red Sox, Giants—all reside in the wings if the money is right.

When was the last time a 28-year-old, centerpiece shortstop hit the market uncompromised by injury or decline? Carlos Correa, perhaps—but even he wasn’t as proven in October. Bichette’s market is fire: estimates soar past eight years, $200 million, and for teams dreaming of the next Francisco Lindor, this is the moment to strike.

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