10 Biggest Storylines Leading Into MLB's Winter Meetings

There have already been a handful of notable signings, re-signings and trades, but the offseason action will kick up a notch in a few days as the baseball world descends upon Orlando for the Winter Meetings. 

Before the hot stove really starts to sizzle and Major League Baseball’s top free agents find new homes, here are the 10 biggest storylines worth tracking ahead of MLB’s annual offseason extravaganza. 

How much does top free agent Kyle Tucker get?

(Photo by Matt Dirksen/Chicago Cubs/Getty Images)

 Tucker won’t approach the record $700+ million deals that Shohei Ohtani and Juan Soto received as the prized commodities of the last two free-agency cycles, but the 28-year-old is the consensus top free agent on the market this winter and should expect somewhere in the $300-500 million range. Injuries have limited Tucker to 214 of a possible 324 games played the last two years, but he has still consistently produced between 4-6 WAR with an OPS over .800 each of the last five seasons. That makes him one of the most impactful outfield bats in baseball, especially when he’s healthy. His well-rounded skills at the plate should draw interest from every outfield-needy team that’s willing to spend. Tucker was reportedly seen touring the Blue Jays’ spring training facility this week, and the Dodgers, Yankees, Mets, Cubs, Giants and Phillies could also be among the teams in the mix. — Kavner

Who lands the NL home run leader? 

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The market for Kyle Schwarber is fascinating, with teams like the Reds, Mets, Red Sox, and, of course, the Phillies all reportedly in the mix for his services. Coming off a career-best 56 home runs and an MLB-leading 132-RBI season, the 32-year-old slugger figures to command $30 million annually on a long-term deal. Schwarber finished second in National League MVP voting after his spectacular walk year. The Phillies are making it a priority to re-sign their designated hitter, but no deal is said to be close between the two sides. With Schwarber’s market heating up, it’s possible, if not likely, one of the most sought-after free agents will come off the board during the Winter Meetings. —Thosar

The top middle infielder 

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It’s a thin market for star infielders this offseason, easily making Bo Bichette the splashiest free agent in the diamond. The 27-year-old shortstop/second baseman is expected to land a long-term contract that eclipses $200 million in overall value. Even though Bichette has publicly stated he wants to return to his homegrown team, the Blue Jays will have to outbid other top-payroll clubs to land him – yes, including the Los Angeles Dodgers. With the reigning champions reportedly a top candidate to sign Bichette, who only increased his value with a .348 batting average and .923 OPS in the World Series, his price tag just might reach astronomical levels. — Thosar

Starting pitching market 

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This year’s top free-agent starting pitchers don’t have the track record of last year’s leading trio of Blake Snell, Corbin Burnes and Max Fried, but there are a handful of pitchers who will command nine-figure deals. One of them is already off the board after the Blue Jays made the first major splash on the pitching market, inking Dylan Cease to a seven-year, $210 million commitment. Could Framber Valdez surpass that mark? Unlike with the position players, there’s really no clear-cut top starter here. It’s more a matter of preference. Cease could make the argument as the top arm in the field, but so could Valdez, Ranger Suarez and NPB star Tatsuya Imai. Beyond that group, Michael King and Merrill Kelly are also among the veteran pitchers who could upgrade a contending rotation.  -Kavner

Relief pitching market

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Devin Williams, Ryan Helsley, and Raisel Iglesias are all off the board, but there are plenty of closers remaining and the market has so far shown that it’s a good time to be a relief pitcher. After both Williams and Helsley secured major multi-year deals coming off of 4.00-plus ERA walk years, the ceiling for top free-agent closer Edwin Diaz just got that much higher. The Mets, Dodgers, Blue Jays, and Yankees should all be in the conversation for him, but a small-market club could pull off a surprising deal for the 31-year-old during the Winter Meetings. Robert Suarez and Pete Fairbanks are in the next tier of solid back-end relievers. It’s a sizable and standout group this offseason. -Thosar

How will the reigning champs retool?

(Photo by Sean M. Haffey/Getty Images)

The Dodgers have their sights set on a three-peat, but after spending lavishly the last two offseasons, it’ll be interesting to see how selective they are this winter. They don’t need another starting pitcher, and sluggers such as Kyle Schwarber and Pete Alonso don’t make much sense for their roster. They need to upgrade the bullpen, but could Tanner Scott’s struggles last year make them hesitant to offer another lengthy contract at a volatile position? If they’re not scared off by that, there are plenty of elite options still to choose from (see above). They could also use outfield help, which makes them potential suitors in the Tucker sweepstakes, though they tend to favor shorter-term, higher-AAV deals than the mega-contract Tucker is likely to receive. Could there be a reunion with Cody Bellinger three years after they unceremoniously non-tendered their former MVP? Or could they take a swing for Bichette and shift him to second? With the Dodgers, anything is possible. — Kavner

How will the looming labor battle impact this winter’s free agency?

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We’re still a year away from the end of the current collective bargaining agreement, but the threat of a work stoppage in 2027 looms, especially if the owners ultimately push for a salary cap. How will that impact free agency this year? That remains to be seen (it’s still early), but so far, nothing looks too out of the ordinary. It’s interesting that four players took the one-year qualifying offer with the uncertainty ahead next winter, and we’ve already seen the Blue Jays give Cease a $210 million deal and the Mets give Devin Williams $51 million after a down year. At least for the league’s annual top spenders, it doesn’t appear that they’ll be spooked off by the ambiguity ahead. In fact, it’s possible there’s a greater desire to lock in their long-term deals now while they know what the economic system looks like. — Kavner

Where do the Japanese stars end up? 

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Corner infielder Munetaka Marakami is most likely to sign during or right after the Winter Meetings with his posting window set to end on Dec. 22. Murakami, 25, is a power threat fit for any of the top contenders, but the Seattle Mariners have an obvious need for an infielder with Jorge Polanco and Eugenio Suarez in free agency. Right-hander Tatsuya Imai may take longer to sign with his posting window running through Jan. 2. Imai, 27, recorded a 1.92 ERA and 178 strikeouts over 163.2 innings in the Nippon Professional Baseball League this season. The final big Japanese name this winter is infielder Kazuma Okamoto, a six-time NPB All-Star with a 30-homer ceiling. The 29-year-old’s posting window runs through Jan. 4. — Thosar

Will a small-market club make a splash? 

There have been rumors of the Pirates and Marlins potentially trying to spend this winter, which would represent a shift for the annually frugal franchises who are currently projected to have the two lowest payrolls in MLB in 2026. Perhaps it’s all just noise to avoid potential MLBPA grievances. After all, nothing of note has happened yet for the league’s cheapest spenders, and there will surely be a lot of "we tried" type comments when the most expensive free agents go elsewhere. But it’s worth keeping an eye on. Last year, the Diamondbacks shocked the MLB world by spending $210 million for Corbin Burnes. The A’s gave Luis Severino their largest guaranteed contract ever at $67 million. Who will that team be this winter? Could the Reds lure Ohio native Kyle Schwarber? Could the Tigers land Alex Bregman? We’re probably in for at least one surprise. — Kavner

The Scott Boras show

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As always, the mega-agent will field questions and propose puns regarding his top free agents in this year’s class sometime at the onset of the Winter Meetings. While Boras’ press conferences always create buzz and draw large crowds, there have been fewer instances of useful information in recent years. Maybe this December, that will change. A top Boras client typically likes to sign during the Winter Meetings, and this year’s candidates are Pete Alonso, Alex Bregman, Cody Bellinger, and Ranger Suarez. Last year, his top free agent was Juan Soto, and he signed his blockbuster contract with the Mets the day before the Winter Meetings. Expect at least one of those top-flight players to come off the board in Orlando. — Thosar

Rowan Kavner is an MLB writer for FOX Sports. He previously covered the L.A. Dodgers, LA Clippers and Dallas Cowboys. An LSU grad, Rowan was born in California, grew up in Texas, then moved back to the West Coast in 2014. Follow him on X at @RowanKavner.

Deesha Thosar covers Major League Baseball as a reporter and columnist for FOX Sports. She previously covered the Mets as a beat reporter for the New York Daily News. The daughter of Indian immigrants, Deesha grew up on Long Island and now lives in Queens. Follow her on Twitter at @DeeshaThosar.