Buster Olney
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Buster Olney
ESPN Senior WriterSenior writer ESPN Magazine/ESPN.com
Analyst/reporter ESPN television
Author of “The Last Night of the Yankee Dynasty”
Jeff Passan
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Jeff Passan
ESPNESPN MLB insider
Author of “The Arm: Inside the Billion-Dollar Mystery of the Most Valuable Commodity in Sports”
Dec 5, 2024, 07:00 AM ET
MLB’s winter meetings begin Monday in Dallas, signaling when baseball’s offseason activity is likely to take off after a relatively slow first month.
All eyes will be on the free agency of superstar outfielder Juan Soto, who is likely to sign by the end of the meetings — if not before they even begin. But Soto is far from the only player who could be in for a huge payday as the baseball world gathers in Texas with Pete Alonso, Willy Adames, Corbin Burnes and Max Fried among the other in-demand free agents looking for their next homes. The trade market also figures to ratchet up in the coming days with Chicago White Sox ace Garrett Crochet highlighting the stars who could be dealt.
When and where will Soto sign? Which teams could land the other players in line for a nine-figure payday and who is looking to make a blockbuster trade?
Here is the latest intel we’re hearing on the players, teams and themes that will rock the meetings — starting with the one name everyone is watching.
When will Juan Soto sign and how will his free agency shape the meetings?
Passan: In a sea of misinformation about Soto’s plans, here is the reality: The end is near. Teams engaged in a third round of Soto bidding this week, and while no deal is imminent, one could materialize before the winter meetings officially begin Monday. Wherever he goes, the contract is expected to set records for length and potentially overall value.
Olney: Soto’s handling of this negotiation is playing out like one of his plate appearances — an extended process, with him thoroughly processing everything that the teams are throwing at him, from their long-term plans to the state of their farm systems to how they intend to allocate payroll in the years ahead. The choices are distinct. He knows from personal experience that Aaron Judge can provide coverage for him, in the lineup and in the clubhouse. The future possibilities for the Mets seem boundless, because of Steve Cohen’s wealth, but they have to construct a pipeline of pitching. Signing with the Red Sox would mean that he’d get to spend the rest of his career playing in a ballpark that augments greatness in left-handed hitters, from Ted Williams to Carl Yastrzemski to David Ortiz to Rafael Devers — although one evaluator notes that Soto could thrive in any ballpark.
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Soto has played this brilliantly. He has left doubt in the minds of those making offers because they don’t know what he really wants, in the end, whether it be getting the most money, playing in New York or some other unknown variable. Whatever Soto decides, his signing will set off a flurry of activity as the losing bidders scurry to find consolation prizes.
Passan: Much of the high-end free agent market has been frozen on account of Soto, and once he chooses a team, those who didn’t get him will pivot to backup plans. With that, a deluge of deals will make the remainder of December one of the busiest baseball-transaction months in recent memory. How many of them come during the meetings could depend on the Soto runners-up’s desire to immediately counteract their disappointment.
Olney: It’s a perfect storm of bidding, and through the use of deferrals, it does not seem out of the realm of possibility that the broad strokes of his deal could be something in the range of $750 million over 15 years.
Passan: It’s an enormous number. It could include deferred money. But less than a year after Shohei Ohtani signed a $700 million contract that shattered the previous record by nearly $275 million, Soto might exceed it.
Which top free agent hitters could be the first dominoes to fall once Soto picks a team?
Passan: Adames’ market is beginning to take shape, and once Soto signs, it’s primed to expand even more. Whether it’s at shortstop, where the San Francisco Giants would play him, or third base, where either New York team would slot him, Adames’ combination of production (32 home runs, 21 stolen bases, 118 OPS+), position (left side of the infield) and age (29) all bode well.
Olney: More than any other player, Adames will benefit from Soto’s final choice, because he fits so many of the bidders. He could be a third baseman for the Mets or the Yankees, and there is confidence among both of those teams that Adames could handle the scrutiny of New York. The Red Sox are in need of a right-handed hitter and Adames could be a fit, although Boston would have to be prepared to move Rafael Devers to a first base/DH type role sooner rather than later, and to move Triston Casas in a trade (presumably for the front-line starting pitching that the Red Sox need).
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Passan: Alonso’s market is likely to take longer to develop than Adames’, though there’s a scenario in which Soto signs, other high-dollar players start coming off the board and the combination of Alonso not wanting to miss out on big spenders and big spenders not wanting to miss out on impact players makes for a quick deal.
Olney: Jeff, I agree that Alonso might have to wait — and unlike Adames, he’s not a great fit for some of the teams involved with Soto. Do the Yankees need power? Sure, but it’s hard to imagine their front office buying into another 1B/DH type on a long-term deal when they still have Giancarlo Stanton locked up for a couple of more years, and with Judge edging toward his mid-30s. The Yankees have been right-handed heavy at times in recent years and it has been a problem against teams with elite bullpens. The Red Sox are already saturated with 1B/DH types, so he’s probably not an option for them. The best possible outcome for Alonso will be if Soto signs with some team other than the Mets, because in the end, Alonso is worth more to the Mets than he is to any other team, as a popular, homegrown player.
I also find the Alex Bregman negotiations to be fascinating because while he’s deeply respected and valued by club executives, some don’t necessarily view him as a $300 million player. Boras, who represents Alonso and Bregman, has waited in the past for deals to emerge, even if it means holding out clients like Bryce Harper and Blake Snell until February or March (or later), and Bregman and Alonso might test the calendar.
What about the remaining free agent aces?
Passan: At the top of the market remains Corbin Burnes, and as much as anyone, he is directly tied to Soto. If a team winds up spending $700 million, it could rationalize doubling down — in the same way the Dodgers did last year with Yoshinobu Yamamoto — and adding Burnes as well. The likelier outcome: One of the teams stung by not getting Soto will pivot to Burnes and give him the eighth $200 million-plus deal ever for a pitcher.
While suggesting that the Max Fried sweepstakes is an AL East-only affair would be an exaggeration, interest continues to come from Boston, New York and Toronto. San Francisco could be in the mix, too. And with the high early prices for free agent starting pitching (annual values for the pitchers who have signed include Blake Snell at $36 million, Yusei Kikuchi at $21 million, Frankie Montas at $17 million and Matthew Boyd at $14.5 million), Fried should do very well.
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Olney: Fried has checked every box for contenders, and like Adames, he might move to the top of the board for the teams that miss out on Soto. The question for both these guys could be: Where do they really want to pitch the rest of their respective careers? Would Fried prefer to stay in the NL East, with the Mets, or would he aim for the highest dollar offer — which could come from Toronto, a team seen by rival execs and agents to be desperate to land high-end talents — and would he be open to pitching in Fenway Park while leading a young Red Sox staff. In the Red Sox’s internal talks, there has been a belief expressed that with the right move, Boston will be positioned to make the playoffs next year and contend for a division title. The Orioles should be in the Fried and Burnes conversations, but we really haven’t gotten a concrete indication that Baltimore’s payroll is going to go to the point that they land one of the highest-price free agents.
How often will Roki Sasaki’s name come up in Dallas?
Passan: Teams haven’t forgotten about him. They are preparing presentations for his eventual posting, knowing that for all the good they can do in free agency this winter, the single most valuable player in terms of surplus value will be Sasaki. When he is posted — it can happen at any point now, as the 45-day window to sign will include dates later than Jan. 15, when the new international amateur signing period begins — Sasaki will take over from Soto as the biggest prize of the winter.
Olney: The conversation about Sasaki echoes what was said about Shohei Ohtani when he was first made available for an MLB deal — all teams will do their due diligence, prepare a sales pitch, get their power points and highlight videos ready, because Sasaki is so great and, at this stage of his career, so affordable. Teams don’t know the player, and don’t know what he really wants. But there is widespread industry belief — correct or not — that Sasaki has probably already picked a team, and it’s most likely the Dodgers. All of these clubs will go through the process, however, and at the end, a lot of execs are going to complain that it was a waste of their time.
Passan: The industry should not forget about the San Diego Padres, Texas Rangers and Chicago Cubs. Nor forget that when Ohtani’s free agent process was playing out, the Los Angeles Angels were never mentioned among the favorites.
Which players are going to be mentioned most in winter meetings trade discussions?
Passan: As prices on free agent starting pitchers remain high, the trade market for Chicago White Sox left-hander Garrett Crochet is starting to percolate. Chicago let teams know it intends to trade the All-Star this winter, and with an arbitration salary estimated around $3 million, Crochet will be one of the biggest bargains in baseball. His salary in 2026, Crochet’s last year before reaching free agency, won’t be significantly higher, and the White Sox accordingly are carrying a hefty price in negotiations. A deal could materialize quickly; it also could come together as more free agent pitchers sign. Regardless, it’s the sort of trade that can make a team’s winter.
Olney: As far as the timing of a Crochet trade, executives are pointing out that White Sox GM Chris Getz has demonstrated that he will wait unless he gets a deal he really wants — as he did with Dylan Cease last offseason, holding onto him until the Padres became aggressive in spring training. When all the best free agent pitchers come off the board, some executives say, that’s when Crochet will become the best option in the market, far and away.
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Interestingly, the perception of some teams is that the White Sox are intent on dealing center fielder Luis Robert, and this is being read as a tell that Chicago wants to cash out on whatever diminished value Robert has now, rather than risk seeing his value crater even more through another subpar season. The 27-year-old outfielder will make $15 million next season, with $20 million club options for 2025 and 2026. “If they really believed he would bounce back, wouldn’t you hang onto him until next summer and look for him to rebuild his value?” asked one rival official.
Passan: Crochet isn’t the only impactful starting pitcher who could move. Tampa Bay is willing to trade starting pitching, and with the Rays playing at Steinbrenner Field this season after Hurricane Milton destroyed Tropicana Field’s roof, their revenue questions have prompted teams to inquire about left-hander Jeffrey Springs, who will make $10.5 million each of the next two seasons and is widely considered a front-half-of-the-rotation starter.
Olney: The St. Louis Cardinals are another team to monitor on the trade front. If Nolan Arenado is dealt sometime this winter, as many expect, then this will help define just how deep the Cardinals’ rebuild is going to be. St. Louis plays in one of the weakest divisions in baseball, while operating with obvious advantages over teams like the Reds, Brewers and Pirates, and yet could be entering a cycle of major reconstruction. The perception of other teams is that if the Cardinals are going to deal Arenado, or the Cubs intend to deal Cody Bellinger, they will have to be prepared to eat significant salary in order to facilitate a deal.
What else are you hearing that will shape the winter meetings?
Olney: In general, the prices paid for the best available free agents are going to be shocking, team officials and agents predict, because there is more need among teams than there are players available.
Passan: Like almost everything this winter, the outfield-bat market is tied strongly to Soto’s destination. Whether it’s Teoscar Hernández, Anthony Santander, Jurickson Profar or Tyler O’Neill, outfielders will start coming off the board once Soto chooses.
Olney: The Orioles can shift the perception of what is possible for the franchise by making deals for high-end starting pitchers, working from their farm system resources or anteing up with dollars. And if they’re going to do it, now is the time: They are in their window to win right now.
Passan: The relief market has been somewhat stagnant, but that should change around the meetings. The best relievers available: Tanner Scott, Jeff Hoffman, Clay Holmes, Carlos Estevez, Kirby Yates, Blake Treinen, Kenley Jansen and David Robertson. They won’t come cheap. Aroldis Chapman’s one-year, $10.75 million contract set a strong standard for relievers.