2023 MLB Winter Meetings Preview

It is time to go shopping and bartering to transform rosters.

While many of the other big U.S. sports leagues rush to free agency on the first few days the market is active, MLB takes its sweet time to really make moves. That could be tradition, thoughtfulness or timing.

But beginning Monday, MLB will conduct its annual Winter Meetings, this year being held in Nashville, Tenn. It is during those meetings — when front-office executives, owners, players, agents and those looking for jobs at various levels of the business all gather in one location — when franchise-altering deals will be consummated. Trades and free agents will grab the bulk of the headlines, with the groundwork for many of those deals being laid at the general manager and owner meetings that have taken place in recent weeks. Other deals will come together quickly.

Not all teams will address every need in Nashville. Some might need more time as they work on other deals or are dependent on the timeline of free agents or trade partners. Rumors will be out of control (as will fake social-media accounts), so make sure to track those you trust (I like to make lists).

As a primer for what could happen, I took a look at free agents, players who could be on move and teams looking to revamp or make that big addition in hopes of winning the World Series — or at least making a postseason push.


What Has Happened So Far?


A few notable signings and trades have happened so far and they mainly have to do with pitching. The most active team so far has been the St. Louis Cardinals, who shockingly finished last in the National League Central. Needing to revamp their rotation — and that needed to happen even before Adam Wainwright’s retirement —the Cardinals signed Sonny Gray (three years, $75 million), Kyle Gibson (one year, $13 million) and Lance Lynn (one year, $11 million). That trio is joined by holdover Miles Mikolas in the rotation. One more starter appears to be needed. Not everyone has changed places, with Aaron Nola sticking with the Philadelphia Phillies for seven years and $172 million, which seems a bit on the club-friendly side for a 30-year-old ace.

Two trades of note thus far has been Atlanta’s nontender deadline deal for left-handed reliever Aaron Bummer to clear salary space and the Arizona Diamondbacks getting third baseman Eugenio Suárez from the Seattle Mariners.


Shopping for a New Home


For many free agents, this is their first (and maybe only) time on the open market and a chance to make life-altering money. With the top of this offseason’s list considered not very deep, many teams will be pursuing the same players, thus leaving franchises out in the cold and scrambling for Plan B, Plan C or worse. Here is a look at some of the top free agents available:

Shohei Ohtani, DH-RHP

The most-coveted name on the market, Shohei Ohtani’s fortunes took a dramatic change late in the season when it was discovered he was going to need Tommy John-type surgery for the second time since coming over from Japan. Ohtani, fresh off his second American League MVP award and the only player in MLB history to do in more than once unanimously, will still get one of the biggest contracts in MLB history, but the elbow injury that is expected to completely sideline him from pitching in 2024 will prompt teams to try and get creative in addressing the right-hander’s pitching future.

The 29-year-old Ohtani, who has accomplished things as a hitter and a pitcher that are unprecedented in MLB history, is still expected to be ready to hit on Opening Day and his left-handed bat plugs into the middle of any lineup. After six years with the Los Angeles Angels, Ohtani been linked to the Los Angeles Dodgers as his free agency approached — and nothing has changed. It would achieve his No. 1 priority of wanting to join a contender. The San Francisco Giants, the Dodgers’ rival in the NL West, are probably the No. 2 team in this battle, needing to make a splash after being jilted last offseason. Other big-money teams will be involved, including the Chicago Cubs, Toronto Blue Jays and the recently crowned World Series champion Texas Rangers.

Prediction: Dodgers just make too much sense.

Cody Bellinger, 1B-CF

After being nontendered by the Dodgers following the 2022 season, Cody Bellinger took a chance at bouncing back with the Chicago Cubs. It paid off and now comes his payday. His positional versatility makes him an atypical free-agent slugger and that will recoup some of the dollars he lost due to the failure the 2019 NL MVP had at the end of the his stay with the Dodgers.

Prediction: Seattle Mariners in a move that precipitates a trade.

Yoshinobu Yamamoto, RHP

The biggest name coming over from Japan this offseason, Yoshinobu Yamamoto is perhaps the hottest name among available pitchers. Having turned 25 in August, the right-hander has pitched most of the last seven seasons for the Orix Buffaloes in Japan’s Pacific League. Yamamoto, who was posted last week and has a 45-day negotiating window, is not expected to sign until after the Winter Meetings, according to a timeline laid out by agent Joel Wolfe. Yamamoto won the last three Eiji Sawamura Awards, Japan’s equivalent of the Cy Young Award.

Prediction: Giants could use another top-flight starter to pair with Logan Webb and need to strike big.

Blake Snell, LHP

Speaking of Cy Young Award winners, it isn’t often that they hit free agency right after taking home the award, but that is the case with Blake Snell. That made him a two-time winner, pairing the one in 2018 with the Tampa Bay Rays with this one with the San Diego Padres. While he doesn’t profile as a true ace, he is a reliable presence at the top of a rotation. The Seattle native could be lured back home, but with the high demand for starters and the Mariners still having to overcome the Houston Astros as well as the Rangers in the AL West, other teams could make a better pitch.

Prediction: Giants due to his success in the NL West and Bob Melvin’s presence.

Jordan Montgomery, LHP

A pitcher who has been traded twice and played for three teams over the last two seasons wouldn’t necessarily be a highly sought after commodity, but Jordan Montgomery’s stock has soared in those circumstances, particularly after joining the Rangers at the trade deadline. A reunion with the Yankees, who drafted him in the fourth round in 2014 but didn’t deem him worthy of keeping around in 2022, wouldn’t be out of the question, but his postseason performance with the Rangers will be attractive to top contenders.

Prediction: Atlanta for a second left-hander and a veteran presence once Charlie Morton retires.

Matt Chapman, 3B

A lot of teams are looking for an upgrade at third base and Matt Chapman will provide that, mostly on defense. The former Platinum Glove winner as a league’s best overall defender when he was with the Oakland A’s, Chapman is only a moderate presence offensively, supplying 25-homer power and only hitting 17 in 2023 with the Blue Jays. The fact that he rates highly on the position-player free-agent list goes to how weak the class is.

Prediction: Chicago Cubs in a no-pressure situation.

Josh Hader, LHP

Maybe because the Padres were a nonfactor for basically the entire season, Josh Hader flew under the radar despite his track record as an elite closer. In fact, Hader had one of his best seasons, which means any contender would love to add him to the back end of their bullpen. That Hader is in line for a big payday goes against the analytics grain in paying for saves, yet there is always a team that will make an exception.

Prediction: Baltimore Orioles to form a super-bullpen and bring Hader home.


Trading Places


Contract situations often dictate player movement and that is very front-and-center with this group of players. Whether entering the final year of arbitration or a franchise-friendly deal signed while still under team control, players become prime trade candidates as they become more expensive the the potential of losing them prompts teams to trade them for prospects rather then just receive a single compensatory draft pick.

Juan Soto, OF

To say that things haven’t gone smoothly with the San Diego Padres following their trade-deadline blockbuster for Juan Soto in 2022 is an understatement. Yes, the Padres made the NL Championship Series in 2022, but 2023 was a disaster and will have ramifications this offseason. Trading Soto, who still has one year of team control before hitting free agency, is likely one of those moves. Why? The Padres apparently have some financial issues and thus are prime candidates to cut salary. Soto might not net the haul the Padres had to give the Washington Nationals, but would get some prime prospects nonetheless for a hitter that has been compared to Ted Williams and just turned 25 at the end of October. The big question is which team will pony up those prospects and has the space to accommodate his projected salary of $33 million?

Corbin Burnes, RHP, and Willy Adames, SS

One of the biggest questions entering the Winter Meetings is: What will the Milwaukee Brewers do? More specifically, will the Crew trade ace Corbin Burnes and/or shortstop Willy Adames? Both are entering their final spin through arbitration and are set to become free agents after the 2024 season. It is because of their increasing price tags (Burnes is expected to make at least $15 million and Adames around $12.5 million) and the Brewers’ reluctance to become a bigger spender. What the Brewers get in return will be dependent on whether the acquiring team gets a chance to negotiate a long-term deal with Burnes, in particular, but being a client of agent Scott Boras might rule that out. A package deal for the pair is also very possible, particularly for a team such as the Dodgers, which could use both to improve their current situation in the rotation and shortstop.

Tyler Glasnow, RHP

Another team that doesn’t like to spend yet is one of the best at churning out talent is the Tampa Bay Rays. Tyler Glasnow returned from injury and pitched like a top-of-the-rotation starter, but is due a raise of almost $20 million and will earn $25 million in 2024. The Rays’ Opening Day payroll in 2023 was just over $73 million. The lack of top-end free agents makes the trade market much more plausible for contenders, especially if they lose out on the top arms on the open market. But like Burnes, Glasnow is slated to become a free agent following 2024.

Dylan Cease, RHP, Luis Robert Jr., OF, and Eloy Jiménez, OF

Unlike Glasnow and Burnes, Dylan Cease has still two years of control by the Chicago White Sox, while Luis Robert Jr. is signed for the next two years with a team option for 2026 and Eloy Jiménez for 2024 with an option for 2025. Having lost 101 games and with a new general manager in Chris Getz, will the White Sox decide to dip into the free-agent market and try and contend in what was the worst division in MLB in 2023, the AL Central? Or will they decide to sell off some of their assets and do yet another rebuild? Much like the Brewers’ situation with Burnes and Adames, there could be a package deal for Cease and one of the outfielders. If they keep all three, the White Sox will go after starting pitching.

Shane Bieber, RHP

One of the few teams that can produce pitching on a regular basis is the Cleveland Guardians, which is why Shane Bieber is potentially available. Like others in this section, Bieber is entering his final year of arbitration and is projected to earn just above $12 million in 2024. Bieber was limited by an elbow injury in 2023, which has slightly depressed his value. But as at least a one-year rental, most contenders would be willing to take a chance on Bieber. Are the Guardians willing to trade their ace? It would seem unlikely with the AL Central wide open, yet the right offer could be tough to pass up. One wild thought: What if the Guardians deal Bieber and acquire one of the other aces on this list?


Making Moves


There are three reasons why teams are active at this time of year. One, they are coming off a disappointing season and still see themselves as a contender. Two, they see the potential of making a move in their division or at least believe they could make a run at a playoff berth. Three, time to rebuild or retool. Already having mentioned a few teams above that could be active — Dodgers and Giants among them — here are others that could join the party.


After looking like a juggernaut for pretty much the entire season, Atlanta exited the playoffs for the second year in a row in the NL Division Series to the Philadelphia Phillies in four games. So what does the team that has most of its core locked up to long-term contracts do? In a bit of a surprise, Atlanta made a deal with the White Sox at the nontender deadline that cleared potential salary as well as 40-man roster space for some moves. That seemed to signal a few moves were anticipated. In addition to adding Bummer from the White Sox, Atlanta also signed right-hander Reynaldo López, who was with the White Sox, Angels and Guardians last season, with a potential of moving Lopez to the back end of the rotation. Adding another starter or improving their situation in left field or shortstop would be the only places in the lineup that need to be addressed. Atlanta’s payroll is already just shy of $200 million, so how far will the front office push that?

Chicago Cubs

After making the biggest managerial move of the offseason, luring Craig Counsell from the NL Central rival Brewers before ousting club icon David Ross, there is a bit more urgency to the Cubs’ offseason. The Cubs were better than expected in 2023, but lost Bellinger, right-hander Marcus Stroman and third baseman Jeimer Candelario to free agency. So there are two priorities: Finding an impact bat and a No. 1 starter. Cousnell values defense and already has a stellar middle-infield defensive pairing in shortstop Dansby Swanson and second baseman Nico Hoerner, so adding Chapman at third base would make a lot of sense. With rookie Pete Crow-Armstrong ready to take over in center field, that leaves first base and catcher as the lone positions to upgrade, whether via free agency or trade.

Detroit Tigers

While this team could easily be in the next category, the moves the Detroit Tigers have made so far this offseason have already declared that 2024 is a year they feel they can contend. While right-hander Kenta Maeda and outfielder Mark Canha won’t significantly alter the Tigers’ odds in the AL Central, they are pieces that will help the Tigers in their push to finish above .500. Finding others to complete the puzzle in a very winnable division will be key to complementing youngsters Spencer Torkelson at first base and Riley Greene in right field. Maeda essentially replaces free-agent left-hander Eduardo Rodriguez, so more adds to the rotation are necessary.


It’s a Mystery


Every Winter Meetings, there are several surprise moves and the ever-present “mystery team” involved in trade or free-agent negotiations. We all know how the big spending of the Padres and New York Mets during last offseason translated into results in 2023, so the guess here is that you see fewer contracts of 10 or more seasons. That also has to do with the quality of the available free agents.

Some teams often feel like they are playing a game of musical chairs and then when they lose out on a certain free agent, they just overspend on someone else to save face. If you have been keeping score throughout this piece, you will notice one team absent from mention: the New York Yankees. It isn’t that they won’t sign anyone, much less anyone of note, it is that I think free agents will approach that situation with caution. Another subpar season in the Bronx is likely to bring major changes for the Yankees. And if you don’t think so, then why was Brian Cashman, the Yankees’ general manager since 1998, so defiant when addressing the media at the GM meetings at the beginning of November?

Regardless, teams like the Rangers, Astros, Phillies, Mets and Blue Jays will be making moves. That is expected. But there will be an unexpected team that will create headlines for what it does. Will it be a team such as the Cincinnati Reds, who have a ton of position-player talent and need pitching? How about the Miami Marlins, who always have pitching and need position players? The Boston Red Sox? The Pittsburgh Pirates?

The Winter Meetings set the tone and the early story lines for the next season and there are plenty of subplots waiting to be written.

Steve Drumwright

Steve Drumwright is a lifelong baseball fan who retired as a player before he had the chance to be cut from the freshman team in high school. He recovered to become a sportswriter and have a successful journalism career at newspapers in Wisconsin and California. Follow him on Twitter and Threads @DrummerWrites.

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