The 2025 MLB Winter Meetings in Orlando have turned into a showcase for one man more than any team: super-agent Scott Boras. With over 20 top free agents in his stable and one blockbuster deal already done, the balance of power this offseason runs straight through Boras’s negotiating table.
The decisions made this week will shape the league’s landscape for years to come.
Scott Boras Sets the Market Early With Dylan Cease’s Mega Deal
Every winter, there’s a contract that sets the bar for free agency. In 2025, Boras got there early, locking in a 7-year, $210 million deal for pitcher Dylan Cease with the Toronto Blue Jays.
This contract does two things: it signals that frontline pitching is still the game’s ultimate premium. It also reinforces Boras’s knack for squeezing out long-term security at elite annual values.
For rival agents and front offices, the Cease deal is now the reference point for any top-tier arm.
How Cease’s Deal Resets the Pitching Market
Boras will use the Cease contract as leverage in talks for other pitchers. Teams hunting for rotation help know the price of upside is steep.
The Blue Jays’ willingness to commit long-term dollars could push other contenders to act aggressively. Nobody wants to wait for bargains that might never come.
Pete Alonso’s Power Bat Headlines the Position-Player Market
Among Boras’s unsigned stars, Pete Alonso is the clearest middle-of-the-order anchor available. The slugging first baseman wants a long-term deal that matches his home-run power and his status as a franchise face.
The market seems focused on two options: a return to the New York Mets or a splashy move to the Boston Red Sox. Both clubs crave impact bats, both can afford big contracts, and both play in markets where power numbers and personality get magnified.
Mets or Red Sox: Where Does Alonso Fit Best?
For the Mets, keeping Alonso is about stability and avoiding the optics of losing a homegrown star in his prime. For the Red Sox, signing Alonso would signal an aggressive push back into contention and give them a cornerstone slugger at Fenway.
Boras will let the leverage build as each team weighs the cost of missing out on elite power.
Alex Bregman’s Boston Future and AL East Intrigue
Alex Bregman added intrigue to the AL East dynamic by opting out of his contract with the Red Sox. Publicly, he’s said he’d like a long-term stay in Boston, but that hasn’t stopped other contenders from circling.
The Yankees and Blue Jays are watching his market, setting up a possible bidding war in one of baseball’s most competitive divisions. Bregman’s October track record and his infield value make him a high-floor investment, even with some mileage on his body.
Will Boston Blink in a Competitive AL East Market?
Boston has to decide if it’ll stretch the budget to keep Bregman away from its two fiercest rivals. Any deal Boras lands here could ripple across the division, where one star changing uniforms can swing the balance of power.
Pitching Depth: Suárez, Gallen, MartÃnez and Scherzer
Beyond Cease, Boras controls a group of arms that could fill different roles on contenders. Each comes with a question mark, but also with upside that pitching-hungry clubs can’t ignore.
Ranger Suárez, the crafty Phillies lefty, keeps drawing interest from teams like the Astros and Braves. Back issues have clouded his long-term durability, but his ability to mix pitches and navigate lineups has made him a quietly valuable target.
Gallen, MartÃnez, and Scherzer: Risk and Reward
Zack Gallen is the classic buy-low candidate. He’s coming off a rough 2025, but his underlying talent and track record suggest a rebound if the right club can help him untangle his recent struggles.
Front offices that trust their pitching infrastructure might see Gallen as a calculated gamble with real upside. José MartÃnez brings versatility—he can start, relieve, or swing between roles over a 162-game grind.
Teams looking for flexible staff options are drawn to pitchers like MartÃnez, who can stabilize multiple spots. Then there’s Max Scherzer, the veteran future Hall of Famer who still gets interest despite age and mileage.
A reunion with the Blue Jays is still possible, while the Giants are another potential landing spot. Scherzer isn’t the same force he was in his prime, but his competitiveness and experience still matter in a postseason chase.
Cody Bellinger and the Japanese Stars: Imai and Okamoto
Cody Bellinger remains one of the offseason’s most fascinating wild cards. His career has swung between MVP-caliber peaks and puzzling troughs, but he found solid footing with the Yankees in 2025.
That performance makes a return to the Bronx his most likely path, especially with New York’s need for left-handed production and defensive versatility. The global side of Boras’s portfolio is highlighted by Japanese standouts Imai and Okamoto.
Both are being closely watched by clubs like the Padres, Mets, and Red Sox, all eager to tap into international star power.
Scouting Imai and Okamoto’s Fit in MLB
Imai’s profile is built on command and pitchability—traits that should translate if he can adjust to the MLB ball and schedule. Okamoto, projected as a power threat at first base, faces a different kind of scrutiny.
Will his bat speed and power play against big-league velocity? And how will his defense hold up over a full MLB season?
The Boras Effect on the 2025 Offseason
As the 2025 MLB Winter Meetings kick off in Orlando, one thing stands out: Scott Boras is once again setting the pace and the price for the entire market.
Big names at almost every position are still hanging out there unsigned. Teams are kind of stuck—they can’t really finish their offseasons until Boras makes his move and the dominoes start to fall.
Whether it’s Alonso’s home-run power, Bregman’s glove at third, Cease’s top-of-the-rotation stuff, or Scherzer’s experience, Boras is steering the winter. If you want star talent, you’re paying the full price this year.
Here is the source article for this story: Ranking the top-10 Scott Boras-repped free agents as the Winter Meetings approach
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