MLB Offseason Transactions We Need To See Happen This Winter

While free agency officially began last Thursday at midnight, just a few minutes after the Los Angeles Dodgers closed out the New York Yankees in Game 5 of the World Series, the Hot Stove season didn’t really begin until Monday. That’s when baseball’s general managers gathered for their annual meetings in San Antonio—and, as of 5 PM EST, when free agents could officially begin signing with teams other than their 2024 employer.

The big dominoes won’t begin falling for weeks, if not months (thank you very much, Scott Boras). But with the general managers all gathered in one place and the landscape becoming clearer for free agents, there should be some movement sooner than later. Here are three transactions we’d like to see transpire, in reverse order of the impact they’d have on baseball’s offseason.

1. New York Mets re-sign Pete Alonso

This feels like one of those teenage relationships where both sides know how good they are together but still find themselves wondering what life would be like with someone else. In the parlance of those times, Alonso and the Mets are now “seeing” other people but haven’t officially yet broken up. (Hold on, going to go listen to some early ‘90s hits for no apparent reason.)

Alonso, whose 226 regular season homers leave him just 26 behind Darryl Strawberry for the all-time franchise lead, appeared on his way out when he set full-season career lows with 34 homers and 88 RBIs. But he changed the narrative in the playoffs by hitting four homers—including the season-saving ninth-inning blast against the Milwaukee Brewers in Game 3 of a wild card series—while posting a .999 OPS. And even before his big October hits, Alonso—blessedly lacking anything resembling a poker face—made no secret how much he loves New York and playing for the Mets. 

David Stearns is the classic emotionless modern executive who has brought his fiscally conscious ways from Milwaukee to New York. The wild card may be owner Steve Cohen, who has been hands-off but is also a Mets fan who knows what Alonso and the franchise mean to each other and has the money to overpay for a guy who may someday have his number retired by the team. 

Don’t make this the end of the road, guys. Pete, you’ll never get over the Mets getting over you and vice versa. Neither one of you really wants to listen to “Release Me” on an endless loop. Reunite and remain together forever (wrong decade, not a ballad, but the right sentiment).

2. Yankees acquire Devin Williams from the Brewers

You can’t ruin a season by trading your closer if you trade your closer before the season! The Brewers, who tanked the morale of a first-place team by dealing Josh Hader to the San Diego Padres in August 2022, basically telegraphed their intentions with Williams on Sunday when they declined his $10.5 million option for next season.

The two sides can still negotiate a 2025 salary—perhaps via arbitration—but there’s no need to go through that process when he can fetch a good return via trade. The Yankees’ bullpen is thin behind late-season revelation Luke Weaver, who could team with Williams to form one of the most formidable 1-2 late-inning punches in the game. Williams would also provide some insurance in case Weaver turns into Clay Holmes, whose out-of-nowhere success story turned sour this season.

The Brewers aren’t going to get Jasson Dominguez or Spencer Jones for Williams, but power-hitting catcher/first baseman Ben Rice would free up Rhys Hoskins for designated hitter duties while also serving as an impressive backup to William Contreras. Five of the Yankees’ top 10 prospects, per MLB.com, are pitchers, including Will Warren, whose stock may be down a bit after he posted a 5.91 ERA at Triple-A and a 10.32 ERA in six games with the big league club. 

3. Dodgers sign Juan Soto

Now we’re having fun. 

As we noted last week, the newly crowned champion Dodgers don’t need Soto. And Soto seemed more comfortable on the east coast with the Yankees and Washington Nationals than he did with the Padres. 

But Soto is going to the highest bidder, even if that team is on Mars. And Soto is sure to appeal to a Dodgers ownership group that has designs on a dynasty—what better way to cement themselves as the team of the 2020s than by adding yet another Hall of Fame-caliber bat—and is as awash in cash as it is in celebrities. Imagine the press conference photo ops with Soto, Magic Johnson and Billie Jean King.

Sure, technically there doesn’t seem to be a spot for Soto, especially if the Dodgers re-sign the popular Teoscar Hernandez to man left field. But Mookie Betts, adept at either middle infield position, can head to second or short to make room for Soto for a couple years. Boras is likely to drag this one out, even by his standards. But don’t be stunned if the Dodgers leave everyone else grinding their teeth in frustration by Valentine’s Day.