This MLB offseason has given onlookers a little bit of everything. We've seen blockbuster trades, massive free-agent contracts and all sorts of transactions in between. And after a lull in December, there has been a late-January flurry of action.
Here are the winners and losers of the MLB offseason so far.
Winner: Jed Hoyer and the Chicago Cubs
Since Jed Hoyer took over as the Cubs' president of baseball operations in 2020, the sport has been waiting for the moment when Hoyer and the Cubs would put their foot down and use their resources to take hold of the division. They'd made some moves over the years, but a big offseason had eluded them, with Hoyer taking his lumps while following a strict budget set by team ownership.
Coming into this offseason, after the team got back to the NLDS for the first time since 2017, there was a need to do something to carry the momentum into 2026. And this winter, Hoyer finally got to do things his way.
One big week turned the Cubs into one of the offseason's biggest winners. Theylanded coveted right-hander Edward Cabrera in a trade with the Miami Marlins, filling their need for starting pitching and strengthening an already solid rotation. Three days later, Chicago made its biggest move,adding All-Star free-agent third baseman Alex Bregman after missing on him last year.
Some wondered if Hoyer deserved his extension after whiffing at last year's trade deadline, but he has now put together Chicago's best team in nearly a decade. With those two big moves plus several additions in the bullpen, the Cubs not only improved their roster significantly but also solidified themselves as serious contenders in the National League and the leaders of the pack in the NL Central.
Loser: Philadelphia Phillies
It's not like the Phillies haven't made moves this offseason. They kicked things off in a big way at the winter meetings, re-signing clubhouse leader Kyle Schwarber to a five-year, $150 million deal. Theyadded Adolís Garcia to their outfield mix, signed Brad Keller for their bullpen and brought back catcher J.T. Realmutto. Yet their offseason feels like a bit of a disappointment.
Philly has been involved with several free agents at the top of the market, the latest being Bo Bichette. The Philliesbelieved they were on the precipice of signing Bichette to a seven-year, $200 million deal. Instead, they were left standing at the altar, watching what would've been their biggest acquisition of the offseason land with the division-rival New York Mets. Plus, southpaw Ranger Suárez signed in Boston, leaving a hole in Philadelphia's rotation.
Now, the Phillies still have a strong starting rotation, and with Schwarber, Bryce Harper and Trea Turner anchoring their lineup, they'll always have some thump and a chance to win. But their offseason is ending on a sour note, their outfield still has some major questions, andthey've yet to resolve the Nick Castellanos situation.
Winner: Toronto Blue Jays
Following a magical run to the World Series, the Blue Jays came into this offseason with one thing in mind: Adding to their roster to get back to the World Series. From the start of the winter, Torontowas in on most of the top free agents on the marketand was not denied in its quest to add an ace-level pitcher. The Blue Jays signedright-hander Dylan Cease to a seven-year, $210 million dealandKBO star Cody Ponce on a three-year, $30 million contract.
But just adding to the rotation wasn't going to be enough, so while they already had a lengthy lineup, the Jaysalso signed Japanese star third baseman Kazuma Okamoto. Adding the 29-year-old boosts Toronto's ability to produce runs and support the newly renovated rotation.
Had the Blue Jays landed their biggest target, free-agent outfielder Kyle Tucker, they would be the unquestioned biggest winners of this offseason. Buteven coming in as the runners-up for Tucker, they've done more than enough to be proud of their winter and put themselves in position to be the American League's best team in 2026.
Loser: Boston Red Sox
There was a path for the Red Sox to come out of this winter as big winners. But at this point, it doesn't feel like that is going to happen. Sure,a starter such as Ranger Suárez is a strong addition to the rotation, which also added Sonny Gray early in the offseason. And after missing out on Kyle Schwarber and Pete Alonso, the Sox acquired first baseman Willson Contreras from the St. Louis Cardinals. But all together, Boston's moves this offseason feel just "fine."
Worse, Boston hasn't addressed its offense in a meaningful way or resolved the log jam in the outfield, with Jarren Duran, Ceddane Rafaela, Wilyer Abreu, Roman Anthony and Masataka Yoshida all still there.
But the biggest miss of this offseason for the Red Sox is undoubtedlyletting Alex Bregman leave and sign with the Cubs. Bregman was Boston's highest priority this winter, yet the team failed to do what was necessary to keep him around and now is left looking to replace him after just one season at Fenway. There's still a little time left for chief baseball officer Craig Breslow to make a move, but it's getting a little late to salvage this winter.
Winner: New York Mets
"Slow and steady wins the race" is the mantra Mets president of baseball operations David Stearns must have been telling himself all offseason when it came to New York's additions. There wasn't a team under more pressure than the Mets this winter, after they missed the postseason following their $765 million investment in superstar Juan Soto.
The Mets started the offseason by moving longtime outfielder Brandon Nimmo to the Texas Rangers andlanding second baseman Marcus Semien in the deal. Then theysigned infielder Jorge Polancoand relievers Devin Williams and Luke Weaver. But those moves weren't enough to move the needle, especially not with the free-agent departures of Pete Alonso and Edwin Diaz.
Well, fast-forward to last week, and just when the Phillies believed they would land Bo Bichette, the Mets swooped in andsigned the two-time All-Star on a three-year, $126 million deal. The move instantly boosted New York's offense and kept a division rival from improving theirs. Then the transactions kept coming this week witha trade to acquire outfielder Luis Robert Jr. from the White Sox.
Still, the Mets' biggest need this winter was starting pitching, and as names continued to come off the board, they were in danger of being left without a dance partner. But with just weeks left before the start of spring training, Stearns finally made his biggest move,acquiring ace Freddy Peralta in a trade with the Milwaukee Brewers.
Much like the Cubs, in just a matter of days, the Metsturned a relatively quiet offseason into a big one. Having accomplished many of their goals for this winter, they can now go into the spring feeling as good as anybody about their roster.
Winner: Scott Boras
Scott Boras is having himself a monster offseason, and as we reach the end of January, baseball's most famous agent has a lot to smile about. Boras was tasked this winter with finding long-term homes for Pete Alonso and Alex Bregman after both essentially signed one-year deals ahead of the 2025 season. One year later, Boras got both what they were looking for, with Alonso signing a five-year, $155 million deal with the Orioles and Bregman landing a five-year, $175 million deal with the Cubs.
As a collective, Boras' clients, including Alonso, Bregman, Cody Bellinger, Dylan Cease, Kazuma Okamoto, Tatsuya Imai, Ranger Suárez and Ha-Seong Kim, have signed $966.5 million worth of contracts this offseason. Witha few more Boras players still on the market, that number could reach a billion.
Boras certainly has his detractors around the game, but you can't deny that the super-agent has delivered for his clients and accomplished what he set out to do this offseason.
Loser: Detroit Tigers
The Tigers are wasting a prime opportunity. In what is the worst division in baseball, Detroit has yet to make any significant additions to its roster, and with one year remaining before the best pitcher on the planet, Tarik Skubal, becomes a free agent, that's a huge miss. The Tigers have made the postseason in back-to-back seasons, and going into this offseason, with the clock ticking on Skubal,it seemed like the perfect time to go for it.
Instead, president of baseball operations Scott Harris and the Tigers have appeared to be caught in between. Besides re-signing reliever Kyle Finnegan, adding veteran closer Kenley Jansen and keeping second baseman Gleyber Torres via the qualifying offer, they're basically the same team they've been for the past two seasons. And now they're going to arbitration with Skubal in what will bea monumental case after the two sides were unable to come to an agreement.
If all this leads to a Skubal trade at the deadline, this winter will go down as a huge whiff for Detroit. And even with the prospects they have on the horizon, if they don't improve the big-league club while Skubal is still around, it's going to be really difficult to convince a fan base that endured a tough rebuild that things are still getting better.
Winner: Los Angeles Dodgers
It would be tough to argue the biggest winners this offseason aren't the back-to-back World Series champion Los Angeles Dodgers. Yes, the rich do indeed get richer, and president of baseball operations Andrew Friedman found a way to fill his 26-man roster with even more star power heading into the 2026 season.
The Dodgers filled two needs they'd been trying to address for a few years now: closer and corner outfielder. And not only did they fill those needs, but in both cases they did it in grand fashion, signing All-Star closer Edwin Díaz andthis winter's No. 1 free agent, Kyle Tucker.
When the Dodgers want something, they usually get it,and this offseason has been no different. But whilethey were aggressive on Díaz, they waited for Tucker's market to come to them. And in giving him a four-year, $240 million deal with a $60 million average annual value, they did whatmany around the sport were afraid they could and would do.
Loser: Major League Baseball
For a few years, there has been a sense around baseball that a lockout is coming after the current collective bargaining agreement expires on Dec. 1, 2026. Much of that feeling has to do with the growing financial disparity across the sport. While it's easy for some to blame a high-spending team such as the Dodgers for "ruining baseball," the situation is more complex than that, with the low-spending teams very much part of the problem. Still, it's not unrealistic to say the Dodgers' financial dominance over the rest of the sport is going to make what was already set to be a difficult fight an even uglier one.
Major League Baseball has a lot of great things going on right now. Young stars continue to emerge each season, attendance and viewership numbers have been strong, and two of the greatest players to ever play, Shohei Ohtani and Aaron Judge, are in the middle of their primes at the same time with big-market teams.
There are plenty of reasons the game of baseball should continue to thrive moving forward. But with the chatter about baseball's haves and have-nots only growing louder, there's a dark cloud looming at the end of the 2026 season, with the industry and fans bracing for an unknown that could include lost games. Unfortunately, that dark cloud now feels unavoidable, and we have no idea how long the storm will last.
This MLB offseason has given onlookers a little bit of everything. We've seen blockbuster trades, massive free-agent ...
