The headliners, the money, and who needs them
With the trade market closed and the clock ticking toward November, front offices are already sketching offers, flipping through comps, and calling agents. This winter’s class has a true anchor in Kyle Tucker and enough name power behind him to stretch the action deep into January. Expect a long, tense winter, because the biggest fish will shape everything from luxury-tax math to draft-pick strategy. And yes, this is shaping up as a classic MLB free agency grind: top stars will move the market early, and then everyone else waits for prices to settle.
Kyle Tucker is the storyline. At 28, the Cubs outfielder brings the exact blend teams pay for: prime-age power, speed, on-base skill, and real defense in a corner with the chops to fake center in a pinch. He opened his first season in Chicago like a rocket—17 homers, 52 RBIs, 20 steals, and a .931 OPS through June—before a hand issue slowed him. Even so, he has stacked 4+ WAR seasons since 2021. That durability and five-tool balance, not one loud spike, is what gets owners to push years and total dollars.
So what does the price look like? Think Corey Seager/Trea Turner territory. Executives I’ve spoken with expect Tucker in the 10-to-12-year range with a total somewhere around $300 million to $360 million, depending on opt-outs and deferrals. If the bidding drags, a structure with an early opt-out after Year 4 could pull in more suitors. If a deep-pocket club wants to end the contest fast, the path is a straight 10-year, mid-$300 million offer with minimal fluff.
Who’s actually in? Start with the Cubs, who traded for Tucker to win and should have every reason to keep him. Add the Giants, who still need a middle-of-the-order lefty to play every day in right field. The Yankees will check in because they always do on top-15 players, though their corner mix and payroll layers make it tricky unless they move money. The Mariners need thump, bat-to-ball, and a trustworthy glove; Tucker answers all three. The Mets can never be counted out. And the Red Sox have been circling a long-term cornerstone bat to put next to their young core.
Alex Bregman is next because premium third basemen are scarce. His glove, command of the zone, and postseason track record keep his floor high even when the slug comes and goes. At 31 next Opening Day, Bregman profiles for 6 to 8 years, roughly $180 million to $220 million. If someone pays him to be “the guy,” it’s at the high end; if he’s a “final-piece” signing, it’s shorter or heavier on incentives. Logical fits: Mariners (need OBP and infield stability), Giants (professional at-bats), Blue Jays (if they shuffle the left side), Yankees (if they don’t like their internal 3B options), and yes, the Cubs if other moves shift their infield puzzle.
Pete Alonso remains the loudest bat among first basemen. Even in a down cycle, 40-homer power ages better than most skills. The chatter around $30 million per year is real, but term is the sticking point. Industry guesses land at 5 to 8 years, $160 million to $240 million. The Mets have every incentive to keep him—face of the franchise, home-run star, marketable—but the Giants, Cubs, and a stealth West contender with cash could force the issue. If the Yankees move pieces at first and DH, they could lurk, but that requires real maneuvering.
Bo Bichette’s bounce-back might be the most valuable turn of the season. After a 2024 derailed by injuries and a .598 OPS, he’s back to barrel-finding form: an .815 OPS, 3.0 WAR in 114 games, and a league-leading hit total. He’s 27, and teams crave that age curve at shortstop, even if the glove grades out as average. His band: 7 to 9 years, around $170 million to $240 million, with escalators if a club believes in the premium hit tool late into his 30s. The Blue Jays have to be seen as favorites to retain, but the Giants, Mariners, and Red Sox all make baseball sense, and a surprise big spender could view him as an anchor for a new window.
Now the designated hitter question that always splits rooms: how hard do you go for a bat-only star? This is where Kyle Schwarber’s market gets interesting. He turns power, patience, and postseason moments into wins, but he’s a DH on most clubs. Expect heavy interest but disciplined years. Early estimates from rival execs: 2 or 3 years, roughly $40 million to $60 million, depending on performance bonuses and plate-appearance triggers. If there’s a bidding pop, it will be for an extra year, not a bigger AAV.
Who could actually sign Schwarber? A few clear fits:
- Phillies: The comfort, the ballpark, and the lineup fit are perfect. If the number is reasonable, a reunion tracks.
- Mariners: They need lefty power and walks. Schwarber checks both while letting them move younger bats around the outfield.
- Giants: Desperate for impact thump. Oracle can mute some hitters; Schwarber’s raw juice plays anywhere.
- Blue Jays: If they retool the middle and want a daily DH who still works counts and changes games with one swing.
- Cubs: A nostalgia angle, sure, but also a real need for left-handed punch if other moves fall through.
- Twins: Budget-sensitive, but if the market softens, he’s a short-term slug upgrade in a tight division race.
One more early move already shaped the first-base lane: Christian Walker, 34, picked Houston for three years and $60 million. That is strong coin for an age-34 corner, but his glove is elite and the power translates in October. The Yankees were in the projections around 3/$65M but didn’t land him. That signing trims the first-base board and nudges Alonso’s leverage up a tick.
Pitching roulette, bullpen money, opt-outs, and how the winter could crawl
The rotation class looked deeper a year ago than it does today. Zac Gallen and Dylan Cease both came into 2025 as nine-figure candidates. Both are 29. Both scuffled. That puts the qualifying offer—projected in the low-$20 million range—firmly on the table. Here’s the calculus: accept one year, reset value with 30 good starts, and hit next winter clean; or decline, carry draft-pick penalties into negotiations, and hope a club still pays full freight. For frontline arms, the draft-cost drag can be real, especially if their stuff or command wobbled this summer.
Teams are split. Some say “buy the dip” on Gallen or Cease with shorter, higher-AAV offers. Others would rather rent a year via the QO than commit $150 million-plus to a pitcher who needs mechanical fixes. The result could be a pitcher stalemate in November that doesn’t break until the Winter Meetings or later.
Meanwhile, a robust closer market is coming. Multiple contenders will pay for late-inning certainty after burning through arms this year. The pattern the last few winters: true closers land 2 to 4 years at $12 million to $18 million per year, setup aces a shade below with heavy incentives. Because bullpens churn, teams will spend here, but they’ll spread risk across two or three signings instead of one mega deal. Watch the Dodgers, Rangers, Orioles, Mariners, and a couple of NL Central teams with sneaky money to deploy.
Opt-outs could flood the pool. Several veterans with strong seasons have clauses that allow them to re-enter the market. When those players jump, it reshapes everything—AAVs move, mid-tier bats wait longer, and clubs sitting just under the first luxury-tax line rethink priorities. For planning purposes, next season’s first Competitive Balance Tax threshold is $244 million. Some owners will treat that as a hard cap. Others will step into the second tier for the right player, accept the surcharge, and just try to avoid the steepest repeat penalties.
The timeline will feel familiar. Free agency opens five days after the final out of the World Series. Qualifying offers go out right away, and players get a short decision window. General managers meet in November, but real action often waits for the December Winter Meetings. Last winter’s rhythm—big names talking early while the rest sat—could repeat. If Tucker moves in December, a lot of other dominos tip fast. If he waits, the market waits with him.
How will teams prioritize? Here’s a snapshot of what they’re weighing in the first month of talks:
- Years vs. AAV: Stars want both. Clubs prefer to pay for prime years and bake in an opt-out to avoid dead money.
- Draft-pick cost: Players tied to qualifying offers can be cheaper in total dollars but cost picks and international pool money.
- Roster fit: DH-only bats clog flexibility. Clubs want one DH slot they can spin through catchers, banged-up stars, and matchups.
- Injury risk: Anyone with recent soft-tissue or hand issues gets an extra layer of medical review before final numbers go in.
- Media and revenue uncertainty: Some teams are still sorting local TV revenue for 2026, which can cap early winter aggression.
Where does this leave the headline names?
Tucker’s market likely settles around four or five serious bidders and a couple of "we’re in if the number dips" clubs. If the Cubs push hard to keep him, they set the pace. If the Giants feel they’re one bat away, they can take the leap. The Mariners have the pitching to make a big offensive swing make sense. The Yankees and Mets can’t be ruled out because there’s no such thing with New York money and pressure.
Bregman will have a broad market because he fits many lineups without forcing position changes. A team that wants him to hit third every day will pay more than a team that wants him as a "pass the baton" on-base machine in the five hole. Expect structure creativity—vesting options, plate-appearance bonuses, and no-trade language—to be a big part of his deal.
Alonso’s decision tree is simpler: if the Mets are close on dollars, the relationship and spotlight keep him in Queens. If they’re not, his power plays in any park, and the Giants and Cubs are obvious baseball fits. His AAV might touch $30 million on a shorter term with outs; on a longer deal, it probably slides into the mid-20s.
Bichette could move fast if the Jays see his second-half health as proof of a full return. If he reaches the open market with momentum, a bidding war between a glove-first club that trusts its infield coaching and a bat-needy club that wants a star shortstop headline is very possible. If his camp leans into bat-first value, a team might try to backload the deal to give itself early payroll space.
Schwarber will have options but may find his best one sits exactly where he is. Clubs love his postseason track record and on-base skill, but every dedicated DH signing locks in a lineup choice 162 times next year. If his market softens, watch for creative structures—mutual options, escalators for postseason rounds, and performance clauses—to bridge a small gap.
Back to the mound: if Gallen or Cease accept the QO, the second tier of starters gets more attention, and that money often spills into bullpens. Expect an early run on relievers once the first $10–$15 million AAV closer signs. Contenders want to lock down high-leverage innings while the rotation dominoes sort themselves out.
One last piece: trades won’t stop just because free agency starts. A few clubs have more pitching than lineup and vice versa. If Tucker or Bregman wait out the market, don’t be surprised if a mid-December trade—an everyday outfielder here, a controllable starter there—reshapes who bids on whom. That tug-of-war between trade capital and cash is going to define this winter as much as any single signature.
For now, circle the dates, sharpen the spreadsheets, and watch the cornerstones. Tucker sets the ceiling. Bregman and Alonso define the middle. Bichette forces teams to pick a lane. Schwarber tests how far clubs will go for a bat-only star. And the pitchers—Gallen, Cease, and a wave of late-inning arms—will decide whether December moves or whether we all wait until the calendar flips.
