The last time the baseball world gathered in person for the Winter Meetings, the three biggest free agents on the market came off the board on three successive days.
This week marks the first time since 2019 that the event will be held in person, and like that eventful week three years ago — which, coincidentally, also took place in downtown San Diego — we could be in for some big-time signings to set the tone for the coming weeks.
The Meetings kicked off in 2019 with the Nationals re-signing Stephen Strasburg to a seven-year, $245 million deal. The next day, it was Gerrit Cole coming off the board, agreeing to a nine-year, $324 million pact with the Yankees. Then came Wednesday, when the Angels landed Anthony Rendon for the same seven-year, $245 million contract that Strasburg had signed just 48 hours earlier.
Here’s a look at four players who could sign at the Winter Meetings:
There isn’t a team in baseball that wouldn’t be better by adding Judge to its lineup, but when you’re talking about a player likely to land a deal worth more than $300 million, the market includes only a handful of teams. In Judge’s case, it looks like a battle between the Yankees and Giants, though some expect the Dodgers to get involved to some extent.
The Yankees — who offered Judge a seven-year, $213.5 million extension back in Spring Training — have made Judge a new offer since the season ended, believed to be worth nearly $300 million over eight years. San Francisco is trying to lure Judge home to Northern California, hosting a visit with the slugger last month, though most believe it will take an offer well above whatever New York’s final number is to pry him out of the pinstripes. Barring the emergence of a mystery team — or the Dodgers — we could see Judge make his decision before the Meetings conclude.
Like Judge, Verlander is seeking a deal worth at least $40 million per season. Unlike the slugger, the soon-to-be-40-year-old is likely seeking a two-year deal (perhaps with an option for 2025), giving his potential suitors a shorter commitment. Max Scherzer’s three-year, $130 million deal last winter seems to be the blueprint for a Verlander contract, with an average annual value (AAV) in the $40-45 million range.
The reigning AL Cy Young Award winner showed no signs of aging in his return from Tommy John surgery, and the second year after surgery is typically even better. The league’s top contenders figure to be the most serious suitors for Verlander, who would surely love to add a third World Series ring to his résumé. If the right situation presents itself to Verlander, he could sign this week — especially now that deGrom has signed with Texas — rather than waiting to see how the rest of the market shakes out.
If Turner isn’t sold on Philly as his destination, he might wait for Judge to sign and hope the runners-up panic and turn to him as an alternative. If Judge does sign at the Meetings, as many expect he will, Turner could very well be the next domino to fall, setting off a chain reaction within the shortstop market.
Despite missing all of 2022 following shoulder surgery, Conforto appears to have a wide range of teams interested in him this offseason. Many expected him to sign a one-year deal to show that he’s healthy again, but the market — which includes the Mets, Yankees, Cubs, Mariners and Astros among others — is strong, so Conforto should be able to land a two-year deal with an opt out after 2023, allowing him to test free agency again after his age-30 season. If one of Conforto’s suitors gets aggressive with an offer, it wouldn’t be a shock to see him sign.
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