In the offseason of 2023-24, Shohei Ohtani's final decision came down to two teams: the Los Angeles Dodgers or the Toronto Blue Jays. The rest is history. After misleading flight logs and a torrid campaign of flattery, the Dodgers won out, as they so often do. Just a couple years later, Ohtani's Dodgers beat the Blue Jays in the World Series.
Toronto has developed an annoying habit of finishing second in almost every major offseason sweepstakes. Juan Soto heavily considered the Blue Jays. So did Corbin Burnes, allegedly. Roki Sasaki, too. Toronto could continue that tradition this winter — or, on the heels of an unexpected AL pennant, GM Ross Atkins may finally cash in and deliver.
Let's canvass 10 of the biggest MLB free agents this offseason to determine which teams will emerge victorious, and more importantly, which teams will come up just short.
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1B Josh Naylor
Predicted landing spot: New York Mets
Second place: Seattle Mariners
The Seattle Mariners probably don't take the leap they did without adding Josh Naylor at the deadline. The Mariners were a couple runs shy of winning the AL pennant, so there has to be increased urgency for Jerry Dipoto and the front office.
And the end of the day, though, free agency is a ruthless business, and Seattle traditionally does not spend on the level of other coastal markets with deeper pockets. The New York Mets in particular appear primed to move on from Pete Alonso. Steve Cohen is the richest owner in MLB, and Naylor fits GM David Stearns' team-building vision far more cleanly than Alonso ever did. He's also available at a lower price tag.
The Mariners will make their push to re-sign Naylor, and there's a good chance he prefers to stick around. When all the cards are on the table, however, Naylor won't be able to pass on New York's cushier offer and a chance to team up with Juan Soto and Francisco Lindor for the long haul.
SS Bo Bichette
Predicted landing spot: Toronto Blue Jays
Second place: Atlanta Braves
Bo Bichette leaving the Blue Jays felt like a foregone conclusion for months. Hell, years. But an incredible run to the World Series — one that ended in bitter extra-innings heartbreak — should motivate both sides to get back together. How could Bichette possibly part with Vladdy after that Game 7? He's more beloved than he has ever been in Toronto and the Blue Jays' pockets are deep enough to hammer out an extension.
As for second place, how about the Atlanta Braves? Few wannabe contenders need a shortstop upgrade more desperately. Bichette could change to second or third base with a different team, but Atlanta can guarantee him a chance to earn his keep at his preferred position. Plus, that Braves roster is still super talented, and Bichette is a southeast kid at heart. He was born a stone's throw away in Orlando.
The Braves can mount a serious push, but at the end of the day, the bonds are too strong in Toronto. Bichette returns for another shot at glory with the team he has spent his entire professional career repping.
DH Kyle Schwarber
Predicted landing spot: Philadelphia Phillies
Second place: Boston Red Sox
The Philadelphia Phillies really should've hammered out a new deal before the season, but alas. Still: Dave Dombrowski, historically, tends to pay his dudes. The Phils have money coming off the books elsewhere and this team cannot afford to lose Schwarber's bat in the middle of the order, especially when the handful of adequate replacements all feel so far-fetched.
That leaves the Boston Red Sox holding the bag. Boston has been heavily connected to Schwarber in recent days, and it's a strong fit on paper. His power would play beautifully in Fenway, as we know from his half-season in Boston in 2021. Schwarber and Roman Anthony trading nukes for the next r32 years is a fun concept.
Unfortunately, Schwarber's roots are too deep in Philly and there's really no excuse for the Phillies to let him walk unless a golden opportunity presents itself (see: Tucker, Kyle). Boston can find its power influx elsewhere. Trust me.
SP Ranger Suárez
Predicted landing spot: San Francisco Giants
Second place: Philadelphia Phillies
Ranger Suárez has time and time again emphasized his desire to re-sign in Philadelphia, with the team he grew up rooting for. Unfortunately, the Phillies need to re-sign Schwarber and prepare for a future with Andrew Painter. That opens the door for another club to win the bidding war and force the southpaw's hand.
Enter the San Francisco Giants. Buster Posey has spent the past couple offseasons big-game hunting. Much like the Blue Jays, San Francisco has no trouble getting big fish on the hook, it's just a matter of reeling them in before the line breaks. Suárez should fall into an accomplishable bucket, much like Matt Chapman and Willy Adames. He can join Robbie Ray and Logan Webb atop the rotation, giving the Giants their clearest postseason path in ages.
The Phillies will sorely miss Suárez's incredible poise and consistency in the playoffs, but the upside of Painter, combined with hopes for a bounce-back campaign from Aaron Nola, will lead Dombrowski to ultimately let Suárez slip away.
SP Dylan Cease
Predicted landing spot: Chicago Cubs
Second place: Baltimore Orioles
The Chicago Cubs appear destined to lose the Tucker sweepstakes, which ideally frees up Jed Hoyer to be aggressive elsewhere. That is not always how things play out in Chicago, of course, but there is pressure to build on the success of 2025. One of their foremost priorities needs to be beefing up the rotation.
Cease tends to fluctuate wildly between Cy Young-level awesome and just fine, but he packs elite strikeout stuff and profiles as the frontline ace Chicago lacks in lieu of Shōta Imanaga. It helps that Cease spent the early years of his career on the South Side in a White Sox uniform. He knows the city.
That brings us to the little engine that couldn't quite, the Baltimore Orioles. Mike Elias allegedly has more spending power under the new ownership group, but that didn't manifest in any significant upgrades last offseason — just a failed attempt to bring back Corbin Burnes. Baltimore could get feisty on the Cease front, but don't count on the O's placing the highest bid when all is said and done.
3B Alex Bregman
Predicted landing spot: Detroit Tigers
Second place: Boston Red Sox
The Red Sox almost have too many good players. There's already an outfield logjam, meaning Jarren Duran or Wilyer Abreu could end up in trade talks this winter. In the infield, Trevor Story's return sets up a difficult decision for Craig Breslow. Of course, Boston prefers to keep Alex Bregman. But at what price, exactly? Marcelo Mayer and Kristian Campbell should be MLB full-timers next season. I don't think Boston really fancies Campbell as a first baseman long term. If the outfield logjam persists and Ceddanne Rafaela needs reps at second base, then it becomes even more difficult to justify going above and beyond to keep Bregman.
Bregman landed in Boston on a three-year, $120 million contract with significant deferrals and opt-outs. He prioritized short-term optionality over long-term stability. After an injury-plagued (but ultimately successful) 2025 campaign, he could shift his priorities this winter. The Detroit Tigers offered Bregman a six-year, $171.5 million contract in contrast to Boston's more flexible deal. That sort of framework ought to appeal more to the 31-year-old this time around.
Detroit president Scott Harris badly needs to stretch beyond his comfort zone and go for it. Tarik Skubal's imminent free agency in 2027 ratchets up the pressure in a palpable way. Bregman has a connection to Tigers manager AJ Hinch, with whom he won a World Series in Houston. The Tigers aren't far off from the upper echelon of contention. Bregman can move the needle, and Detroit needs him more than Boston, frankly.
1B Pete Alonso
Predicted landing spot: Boston Red Sox
Second place: Texas Rangers
It almost feels like a forgone conclusion that Pete Alonso will depart the Mets this offseason. That's a strange feeling, as Alonso has become synonymous with Mets baseball over the years. But he's an aging first baseman, trending toward DH status, and it's unlike David Stearns to hand a player in Alonso's bucket the long-term contract he wants — and deserves.
Few MLB contenders need more help at first base than Boston. The Red Sox are becoming more aggressive with their spending, and Bregman's hypothetical departure opens up a bunch of payroll space. You could argue that, given the construct of this Red Sox roster, Alonso might be more valuable at the end of the day. His power would play beautifully behind Roman Anthony toward the top of the Boston lineup.
The Texas Rangers feel like a reasonable contender for Alonso's services. A disappointing 2025 campaign left the folks in Arlington hungry for major change, and Texas currently has a gaping hole at first base. Alonso's slugging pops a heck of a lot more consistently than Jake Burger's does, to be blunt. That said, Boston is a more appealing destination. Alonso won't pass up a chance to stay in the Northeast and compete for a title in historic Fenway Park.
OF Cody Bellinger
Predicted landing spot: New York Yankees
Second place: Philadelphia Phillies
The New York Yankees can't let both Cody Bellinger and Trent Grisham depart, at least not without an adequate replacement. Bellinger should have no qualms about returning to the Bronx. It can be difficult to re-sign Scott Boras clients, but the Yankees are the Yankees, equipped with endless corporate capital and a healthy dose of organizational prestige to help sway Bellinger's decision. He's valuable to the Yankees not only for his offense behind Aaron Judge, but for his excellent defense — a description that applies to too few Yankees right now.
That said, don't discount a push from the Phillies, even if Schwarber re-signs. The potential departures of JT Realmuto, Suárez, Max Kepler and Harrison Bader give Dombrowski some cash to throw around. No team needs outfield help more than Philadelphia, even if Bellinger's lefty profile isn't exactly what the Phillies need. Dombrowski seldom shies away from a winnable star pursuit, and Boras knows that front office well.
At the end of the day, though, the Yankees are an insurmountable force, angling to move Bellinger to center field to accommodate Jasson Domínguez in left and Judge in right. Bellinger felt how close New York was to something special this past season. He won't leave unless the Yankees just don't pay up, which feels improbable.
SP Framber Valdez
Predicted landing spot: New York Mets
Runner-up: San Francisco Giants
Framber Valdez is probably the best, or at least the most established, pitcher available on the open market this winter. The Houston Astros are going to politely bow out, which clears the way for the most desperate suitor. Enter the richest owner in MLB, Steve Cohen, whose Mets are most certainly itching for quality pitching.
The emergence of Nolan McLean helps to stabilize things a little bit, but New York's deeply undependable rotation was the chief culprit behind its late-season collapse. Valdez, 31, is an incredibly consistent performer, which translates to the postseason. He has not posted an ERA above 4.00 since 2019. The Mets can set and forget him as their leading man on the mound.
In second place come the Giants, a team with the resources and the motivation to tempt Valdez. He'd form an incredible three-man rotational gauntlet with Logan Webb and Robbie Ray. Buster Posey is a committed and persuasive figure, but in the end, the Mets can outspend anyone and New York presents the more appealing opportunity to win at the highest level. And thus, San Francisco is left holding the bag here and pivoting to alternatives (see: Suárez, Ranger).
OF Kyle Tucker
Predicted landing spot: Toronto Blue Jays
Runner-up: Chicago Cubs
After finishing second for Ohtani and quite possibly for Soto, the Blue Jays finally finish the job and attract the offseason's biggest fish. It's a fitting capstone to a miraculous come-up for Ross Atkins and company. Suddenly, Toronto is one of the most desirable landing spots in MLB. That lineup is airtight and Tucker only adds to the Blue Jays' overwhelming depth. He's such a Blue Jays hitter — equally adept at generating solid contact to all areas of the field or just ripping one over the wall.
In second: the Chicago Cubs. The Cubs aren't going to win the bidding war, but Jed Hoyer should at least put up a fight. Tucker is too valuable to Chicago — and the Cubs gave up too much in the trade to just let him walk a year later. The Dodgers and Yankees also figure to factor in here, but Toronto can match the Yankees dollar for dollar. As for L.A., it's just hard to imagine the Dodgers actually shelling out another half-billion to fix a minor weak point in the outfield, but it's the Dodgers. So perhaps this is wishful thinking.
Chicago has the benefit of incumbent status. Tucker, by all accounts, enjoyed his time on the North Side, and it's not like the Cubs are ever actually lacking for resources. It's on the Ricketts and Hoyer to pony up and spend the mountain of cash that organization rakes in every season. Alas, this one goes to the Blue Jays — a real warning shot the rest of MLB, as Toronto isn't going anywhere.