One burning question for each team at the Winter Meetings

December 5th, 2024

We're mere days away from the annual Winter Meetings, which will take place in Dallas from Monday through Dec. 12.

One of the top events on the baseball calendar, the Winter Meetings allow each team to make significant moves in free agency or via trade. At the 2023 Winter Meetings in Nashville, the Yankees acquired Juan Soto from the Padres, while the '22 edition in San Diego saw Aaron Judge, Trea Turner and Xander Bogaerts sign massive free-agent deals.

What's in store for the '24 Winter Meetings and what are the burning questions for each team? We asked each of our 30 MLB beat writers to find out.

American League East

Blue Jays: What is the future of Vladimir Guerrero Jr.?
Everything the Blue Jays do comes back to this question, with Guerrero scheduled to hit free agency following the 2025 season. If the club can extend Guerrero, that swings the window open for the next decade to build -- and spend -- around their homegrown star. If Guerrero walks and the Blue Jays don’t land a top-end free agent this winter, then there’s reason to worry that this organization could take a step back to retool in the near future. If you’re a free agent talking to the Blue Jays this winter, it’s one of the first questions you’re asking. Guerrero’s resurgence in ‘24 reestablished him as the face of the franchise, and beyond the baseball implications, extending him would do wonders with a fan base that’s had its patience tested in recent years. -- Keegan Matheson

Orioles: How much will they actually spend?
General manager Mike Elias has repeatedly emphasized that Baltimore’s new ownership group -- led by control person David Rubenstein, a private equity billionaire -- will give the club the necessary backing to make big moves. But Elias and his baseball operations department will still lead the decision-making process in terms of free-agent signings, and they’re not going to ask for money to throw around just for the sake of saying they finally did so. The O’s brass plans to act diligently, making smart investments for the long-term future of the franchise. With that being said, the Orioles could see a significant bump in payroll for 2025. Could that include a megadeal for the likes of Corbin Burnes or someone similar? We’ll have to wait to find out. -- Jake Rill

Rays: How will they improve their offense?
It’s been a relatively quiet offseason for the Rays on the transaction front, with most of the club’s big-picture focus on assessing the state of hurricane-damaged Tropicana Field, finding a temporary home in Tampa’s Steinbrenner Field and determining the future of their planned ballpark. But there’s no doubt they still need to improve a lineup that scored only 604 runs last season, second fewest in the Majors. Much of that will have to come from within, but they could seek upgrades during the Winter Meetings. They aren’t known for big signings, but could they find a bat in free agency? Are they willing to swap some pitching depth -- perhaps a starter like Zack Littell or Jeffrey Springs, or a top reliever like Pete Fairbanks -- for a proven bat? Will their pursuit of a catcher yield a capable defender who can lengthen their lineup? -- Adam Berry

Red Sox: Can the Red Sox get Juan Soto?
When the offseason started, the Red Sox weren’t taken seriously in some circles as suitors for Soto, the top free agent on the board. Perhaps because the team hasn’t made any big external signings in the last few years. But Boston’s ownership and front office are committed this offseason to bringing a winning team back to Fenway Park, and there would be no more aggressive way to start that quest than to sign Soto, who will likely land a contract between 12 and 14 years in length with a total value of more than $600 million. A generational left-handed hitter, Soto could take pressure off Rafael Devers, who doesn’t enjoy being considered the face of the franchise. Soto would also make Boston a more appealing destination for other prospective free agents. -- Ian Browne

Yankees: Will Soto re-sign, and if not, then what?
The Yankees believe they have made a strong pitch to retain Soto, underlining that he just had the best offensive season of his career while helping the club return to its first World Series since 2009. There are plenty of reasons why Soto should want to return, including the appeal of hitting in front of Aaron Judge for the rest of his career. Whether Soto re-signs or not, the Yankees do have other issues to address: second baseman Gleyber Torres is a free agent, as is first baseman Anthony Rizzo and left fielder Alex Verdugo. None of the three is likely to return. They’d also like to add a starter and need to replenish the bullpen. Yankees brass is ready to make Soto their highest-paid player, but little can be done until they have an answer. -- Bryan Hoch

American League Central

Guardians: How will the pitching get better?
Matthew Boyd is off the board after agreeing to a two-year deal with the Cubs. Now what? The Guardians ended the season knowing that Boyd, Alex Cobb and Shane Bieber would all be free agents and all had interest in coming back to Cleveland. Boyd, given his performance in his small sample size in 2024 on top of his tremendous impact on the clubhouse, was probably No. 1 on that list. Cobb can still return, but the Guardians didn’t have as great of a look at him considering nagging injuries kept him from pitching much. Bieber would be great, but is it enough to sign someone who wouldn’t be ready to pitch until the summer? If the answer isn’t within this trio, who may the Guardians try to sign? Can they afford the talent they need? Will they have to make a blockbuster trade to secure it? There are a lot of questions to answer. -- Mandy Bell

Royals: Where will they find their next offensive upgrade?
The Royals already got one big item checked off of their priority list this offseason when they traded for Jonathan India (and young outfielder Joey Wiemer), sending Brady Singer to the Reds. India, a second baseman whom the Royals think can increase his versatility defensively, will slot into the leadoff spot in the lineup, getting on base for Bobby Witt Jr. That one move alone deepens the Royals' lineup, but they don’t view it as complete yet. Now, they’ve turned their search to a bat that can fit in the middle of the lineup, behind Witt, Vinnie Pasqauantino and Salvador Perez. Someone who can not only get on base, but also add power in the heart of the order. The Royals are evaluating the free-agent and trade markets here, and the open positions for an upgrade include third base and the outfield. -- Anne Rogers

Twins: Do they shake up the core?
There’s a version of this offseason where the Twins look at the pieces they have in place -- a rotation anchored by Pablo López, Joe Ryan and Bailey Ober; a lineup anchored by Carlos Correa, Byron Buxton and Royce Lewis; a solid bullpen and talented but inconsistent complementary hitters -- and find good reason to run it back. There likely won’t be much room for free agency with their financial constraints, anyway, so making real changes to their team would likely involve trading away some of those meaningful pieces. On the one hand, if you trust your talent, you stick with it. On the other hand, the team so very clearly amounted to less than the sum of its theoretical parts amid its season-ending collapse. It’s easy to point to Chris Paddack and Christian Vázquez as potential trade pieces -- but could there be more? -- Do-Hyoung Park

Tigers: Is now the time to trade prospects or bump up the payroll (or both)?
The Tigers have clear needs if they want to take the next step off their first playoff berth since 2014, with a more diversified, consistent offense near the top of the list. But with a free-agent mega-contract unlikely, president of baseball operations Scott Harris has to weigh waiting out the free-agent market in hopes of an opportunistic upgrade, or leveraging their organizational depth to jump into a robust trade market. Harris has been consistent about leaving opportunities open for young players, but that might not be realistic if they add an impact bat. -- Jason Beck

White Sox: Who will remain from the previous core?
The focus remains on young talent acquisition during Year 2 of this latest rebuild for the South Siders, but with free agency not being a major focus, they will use some of their current core via trades to make those additions. Left-handed starter Garrett Crochet, the American League Comeback Player of the Year, has garnered the most trade talk to date, and while it’s tough to deal away a 25-year-old ace with two years remaining of contractual control under arbitration, he’ll also generate the biggest return. A trade of Crochet has to have that effect within the context of the White Sox future hopes. Center fielder Luis Robert Jr. and first baseman Andrew Vaughn also could be on the market. General manager Chris Getz will be in intent listening mode but also won’t force anything just to make a move at the Winter Meetings. -- Scott Merkin

American League West

Angels: How much more will the Angels add this offseason?
The Angels have already been the most active club this winter, signing free agents such as lefty Yusei Kikuchi, right-hander Kyle Hendricks, catcher Travis d’Arnaud and infielder Kevin Newman, while also trading for slugger Jorge Soler and utilityman Scott Kingery. But Angels general manager Perry Minasian indicated they are not done improving the club. It’ll be interesting to see if the Angels swing a big trade for a bat or an arm and how much more they are willing to spend in free agency. They could use another starting pitcher, bullpen help and a corner infielder with power even after the additions they’ve already made. Kikuchi is likely their biggest splash, as he signed for three years and $63 million, but Minasian hasn’t ruled anything out. -- Rhett Bollinger

Astros: Will they re-sign free agent third baseman Alex Bregman?
The Astros have called re-signing Bregman their top offseason priority, and they’ve reportedly made an offer to the third baseman. Bregman is the second-best free agent position player on the market behind Juan Soto, so he may have to wait until Soto signs to get a clearer picture of his future. The Astros desperately want Bregman back – and second baseman Jose Altuve has pleaded for his return – but it will come down to money. Astros owner Jim Crane has never guaranteed more than five years to a free agent, and the biggest deal he’s given to any player is the $151 million that Altuve received with his extension in 2018. It will take a club-record deal to keep Bregman in Houston. -- Brian McTaggart

Athletics: Are free agents willing to sign to play in Sacramento?
Back at the General Managers Meetings in San Antonio last month, GM David Forst expressed uncertainty over what the appetite might be for free agents to sign with the Athletics knowing they will be sharing Sutter Health Park in West Sacramento with the Triple-A Sacramento Rivercats for at least the next three seasons. That question may have been answered in part on Thursday, though, when the A's agreed on a franchise-record three-year, $67 million deal with right-hander Luis Severino. The A’s believe their young squad can take a big step toward getting back to playoff contention in 2025 by addressing their needs at third base and starting pitching, and the Winter Meetings will provide a clearer picture as to how they might go about making those offseason additions. -- Martín Gallegos

Mariners: Will they make their big move in Dallas?
Throughout their tenures in Seattle, president of baseball operations Jerry Dipoto and general manager Justin Hollander had done most of their offseason transacting, or at least a chunk of it, before the Winter Meetings. But that hasn’t been the case in 2024, based on what they believe are a limited number of needs, the avenues they intend to explore filling them and the payroll with which they’re operating. But given that they’ll finally be immersed with the rest of the baseball world, there’s a strong chance they at least lay the groundwork for finalizing their 2025 roster. -- Daniel Kramer

Rangers: Can they re-sign Nathan Eovaldi?
President of baseball operations Chris Young has emphasized multiple times this offseason that bringing back Eovaldi will be a priority. The right-hander tossed 314 2/3 innings across two seasons with the Rangers, becoming the ace of the staff after Jacob deGrom went down with an elbow injury just a month into 2023. Texas is losing significant innings between Eovaldi and Andrew Heaney both becoming free agents, but 2025 looks more manageable if Eovaldi and the Rangers agree on a deal to bring him back. On top of his on-field production, he's a leader in the clubhouse and the coaching staff leans on his mentorship of young pitchers throughout the season. Bringing him back will allow the rest of the winter plans to click into place. -- Kennedi Landry

National League East

Braves: How will the Braves replace Max Fried?
An obvious option would be to re-sign the veteran left-hander who stands as one of this year’s top free agent starting pitchers. But unlike with recent free-agent departees Freddie Freeman and Dansby Swanson, there has never been a sense Fried will re-sign with Atlanta. Spencer Strider will likely miss the season’s first month while recovering from elbow surgery. So, the only current locks for Atlanta’s Opening Day rotation would be Chris Sale, Reynaldo López and Spencer Schwellenbach. Reuniting with Charlie Morton or signing another free agent starter is a top priority for a team also in search of at least one outfielder and at least one reliever. -- Mark Bowman

Marlins: Will the Marlins deal from their pitching depth?
Controllable starting pitching is a commodity, and the Marlins have 11 of those arms on their 40-man roster. Clubs will likely inquire about lefty Jesús Luzardo, righty Edward Cabrera – and even ace Sandy Alcantara – despite injuries. It's up to Miami's front office to determine whether trading from MLB depth is the best way to improve upon the NL's lowest-scoring lineup. Due to those injuries, the Marlins pivoted and dealt from their bullpen depth at this year's Trade Deadline. -- Christina De Nicola

Mets: Will the Mets sign Soto?
It may seem unfair to pin the success of New York’s entire offseason on Soto, considering there’s always been a strong chance he heads back to the Bronx. Yet Soto is a unique talent, the Mets are clearly pursuing him with vigor, and if they miss out on him, it will be difficult to excite the fan base quite as much with any other acquisition. If the Mets do land Soto, it will do wonders to bolster their reputation as perennial contenders. If they don’t, their offseason path becomes a bit more complicated. In either case, they stand a good chance of having their answer before leaving Dallas. -- Anthony DiComo

Nationals: How big will the Nationals go in free agency?
With a young core in place and Patrick Corbin’s $140 million contract off the books, the Nats have both a foundation and financial flexibility this winter. The Nationals could enhance their roster with a veteran player who brings experience and leadership to provide insight to players such as top prospect Dylan Crews and James Wood, as well as offensive power to a lineup that has struggled with run production. -- Jessica Camerato

Phillies: What’s the big move going to be?
Everybody expects the Phillies to do something significant this offseason, but what exactly will it be? They have expressed interest in Soto, but they have said publicly they do not expect to sign him. It’s not a surprise. While Phillies president of baseball operations Dave Dombrowski loves star players, he has made a point this offseason to say he doesn’t think the Phillies need to add another high-priced star. Of course, the Phillies probably need another high-impact bat in the lineup. There’s just too much swing-and-miss in there. So how do they do it? It might come via trade, which makes things interesting. It’s why Alec Bohm and Ranger Suárez and top prospects like Aidan Miller, Justin Crawford and others have been mentioned in trades. -- Todd Zolecki

National League Central

Brewers: How long can they keep the window open?
Everyone expected the Brewers to take a step back last season after trading Corbin Burnes and cutting some payroll, but they instead won the NL Central for the second straight season and the third time in four years. Now their home run and RBI leader (Willy Adames) is gone to free agency, their All-Star closer (Devin Williams) is on the trade block because he’s heading into a contract year, and payroll could be tight again. With the Cubs ascending and the Pirates looking tougher with their terrific young starting rotation, can the Brewers find enough value in trades and under-the-radar signings to plug the pitching, find a productive shortstop and continue a stretch of six postseason appearances in the past seven years? -- Adam McCalvy

Cardinals: Who stays and who goes among the veteran players?
When the Cardinals made the bold decision to “reset” their focus and shift toward developing their young core, it was a jarring feeling for those not used to seeing the Redbirds not in hot pursuit of a 12th World Series crown. It also had to be unpleasant news for veteran players who either signed with the Cards or waived opt-outs to remain with what they thought would be a perennial winner. Willson Contreras agreed to move to first base, and Sonny Gray told the team he wanted to stay in St. Louis, not too far from his offseason home in Nashville. Nolan Arenado, who wants to win a World Series in the twilight of his career, might waive his no-trade clause if the Cards can find a contending team willing to swallow most of the $74 million that he’s still owed. NL Reliever of the Year Ryan Helsley will see his salary for 2025 jump, and then he’s a free agent after the season. One of the game’s preeminent closers, Helsley could command the largest haul of prospects among the Redbirds' trade chips. Pitchers Miles Mikolas and Steven Matz, on the other hand, could be moved just to clear their salaries off the books. -- John Denton

Cubs: Are they really considering a Cody Bellinger trade?
The working theory entering the offseason was that Bellinger would opt out of his deal and hit the open market. Instead, the veteran outfielder exercised his $27.5 million player option for ‘25. At the GM Meetings in November, Cubs president of baseball operations Jed Hoyer said: “Anytime a really good player decides to stay with you, that’s good news.” True, but that decision also limited the front office’s roster and financial flexibility to address the offense. Now, Bellinger has another opt-out clause after next season ($25 million or a $5 million buyout for ‘26), adding a complicating factor to any trade talks. That said, it makes sense for the Cubs to at least explore the market for Bellinger, especially with teams that may miss out on signing Soto. -- Jordan Bastian

Pirates: Do the Pirates dangle pitching in a trade?
The Pirates have a spoil of riches in the rotation and the game's deepest collection of prospect pitchers down on the farm. They also have big needs in the big league lineup and bullpen. It’s hard to see the Pirates dealing any of their top three Major League or Minor League arms, but the depth they have could be the center of a package to improve the Major League team. Does a deal start to take shape in Dallas? -- Alex Stumpf

Reds: Is there enough financial room to fill the remaining needs?
Once free agent pitcher Nick Martinez accepted the one-year, $21.05 million qualifying offer, it brought Cincinnati to $57.75 million in contracts committed to players for 2025. The Reds' payroll figure for next season isn't public, other than a front-office commitment to it remaining either at or above the roughly $100 million that was spent in 2024. “We’ve got a little bit of flexibility right now," president of baseball operations Nick Krall said on Monday. The club still needs to add to its offense -- most likely in the outfield -- while also upgrading defensively and filling out the bullpen. -- Mark Sheldon

National League West

Diamondbacks: How do they make up for the losses on offense?
The Diamondbacks led the Majors in runs scored last year, but they are losing some key pieces from their lineup with first baseman Christian Walker and the designated-hitter platoon of Joc Pederson and Randal Grichuk all hitting the free-agent market. It’s possible the Diamondbacks could re-sign one or more of those players, but it seems unlikely given what the market looks like. That means GM Mike Hazen will need to once again find an undervalued player -- like Pederson last year -- or perhaps use his surplus of starting pitchers to acquire some offense. -- Steve Gilbert

Dodgers: Will Teoscar Hernández be back?
The Dodgers’ top priority this offseason was to add a top starting pitcher to their rotation. They accomplished that early on this winter after signing Blake Snell to a five-year, $182 million deal. But now, the focus shifts to the offense. The Dodgers still need to add one impact bat to the lineup. Will that be Teoscar Hernández? The veteran outfielder was an integral member of the lineup that carried the Dodgers to a World Series title in ‘24. Talks have continued since the season ended, but the time in Dallas could help expedite a resolution. -- Juan Toribio

Giants: Will they make any bold trades?
The Giants rarely traded off the big league roster under former president of baseball operations Farhan Zaidi, but they might be more willing to deal now that Buster Posey is calling the shots. The Giants recently agreed to a one-year, $9.25 million deal with outfielder Mike Yastrzemski to avoid arbitration and tendered contracts to first baseman LaMonte Wade Jr. and reliever Camilo Doval, but all three have been mentioned as possible trade candidates and could be moved to address other roster needs this winter. -- Maria Guardado

Padres: What is Preller’s level of aggressiveness this winter?
The Padres are coming off a 93-win season that qualifies as the best regular season in the 10-year tenure of general manager A.J. Preller. The bulk of their roster returns for 2025 -- but there are still some glaring holes, and Preller has yet to move to fill any of them. Catcher Kyle Higashioka signed with the Rangers this week, leaving a vacancy behind the plate. Jurickson Profar remains a free agent, despite both sides seemingly favoring a return. There are holes in the rotation and, to a lesser extent, the bullpen. Preller has never shied away from major offseason signings or trades. But with a depleted farm and not much financial wiggle room, it’s hard to see a path to a serious shakeup in San Diego. -- AJ Cassavell

Rockies: How much talent will be added vs. keeping the path clear for prospects?
A tight payroll and a legitimate thought that prospects can answer their burning questions (even if it takes a couple of seasons) seem to point to the Rockies being quiet in Dallas. However, there are a couple of holes. The club non-tendered second baseman Brendan Rodgers, and that’s the position where they most likely will seek a starter. Ideally, the Rockies would like to start the year with an experienced regular – much the same way they used Jose Iglesias at shortstop in 2023 until Ezequiel Tovar was deemed ready. Now, it’s prospects Adael Amador (Rockies No. 5) and Ryan Ritter (Rockies No. 12) who are not quite knocking on the door but could be after developing their games. A proven corner-outfield bat is needed, but the likely scenario is the Rockies allow Jordan Beck a chance to show his wares after a fractured left hand hampered his debut in 2024, or grant new chances to Sean Bouchard and Sam Hilliard to join Brenton Doyle and Nolan Jones in the outfield. Behind Beck are more prospects -- Zac Veen (MLB Pipeline No. 83), Yanquiel Fernandez (Rockies No. 4) and Benny Montgomery (Rockies No. 16) -- whom the Rockies don’t want to block. -- Thomas Harding