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Questions abound as face-to-face baseball winter meetings return

Aaron Judge's destination? That's one of the key questions that could be answered during the winter meetings. (AP Photo/Eric Gay)
7 min

Baseball’s annual winter meetings will be held in person for the first time since 2019 this week in San Diego. After three long, remote years, Major League Baseball’s top executives and agents will be able to text each other about potential trades and free agent deals from suites down the hall instead of offices across the country.

In 2020, the coronavirus pandemic forced MLB to cancel the annual event. In 2021, the owners locked out the players amid negotiations for a new collective bargaining agreement. Not since the Washington Nationals reigned as the latest World Series champions have these meetings taken place in their traditional form — and that, frankly, feels like a decade ago.

Whether the relative proximity of baseball’s decision-makers will result in a flurry of transactions remains to be seen. Until this weekend, the offseason market had been relatively quiet. The Blue Jays and Mariners made the most noteworthy trade, with Toronto offloading highly productive outfielder Teoscar Hernandez to Seattle in exchange for pitching. The most high-profile free agent signing to date was the New York Mets’ handing free agent closer Edwin Diaz $102 million for five years.

Then the Texas Rangers announced a five-year deal with Jacob deGrom, a move that took one of the winter’s biggest available stars off the market and left the Mets to join the fray of suitors for aces such as Justin Verlander and Carlos Rodón. Potential big spenders such as the Los Angeles Dodgers, New York Yankees and San Francisco Giants have yet to signal their priorities, but they may need to do so soon, lest they miss out on the top-tier talent available.

And while they sort out those priorities, one of the biggest changes in the new collective bargaining agreement — the addition of a draft lottery — will manifest itself for the first time this week. A Hall of Fame committee will vote Sunday night to determine the fates of steroid era stars such as Roger Clemens and Barry Bonds. Questions abound. Answers are coming.

So for now, here are five key questions that will probably be answered, to some extent, in San Diego this week — as long as the cellphone reception is good.

Where will Aaron Judge sign?

The most dominant storyline of this offseason has been the availability of a unique free agent fresh off an uncommonly dominant offensive season, Aaron Judge. Judge, of course, turned down the Yankees’ offer of a seven-year extension worth $213.5 million before the 2022 season, then proceeded to become the first American League player to hit 62 homers.

Yankees General Manager Brian Cashman told reporters that his team has made an updated offer to Judge since the season ended. Giants GM Farhan Zaidi said last month that his team would have the money to handle any one of the top available stars — including, the implication was, northern California native Judge. And the Dodgers didn’t exactly rule out a pursuit, either. When it comes to top available talent, they never do.

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Whether the lack of a Judge decision has stalled the top of the free agent market is unclear. While the Yankees would almost certainly have to pivot if he signed elsewhere, he is a unique player in this class — unlike the elite shortstops on the market, who offer teams a more complicated choice.

Will the shortstop market start to move?

Last year at this time, the free agent shortstop class was loaded with talent, including eventual Minnesota Twin Carlos Correa, eventual Ranger Corey Seager and eventual Boston Red Sox second baseman Trevor Story. But this year’s class may be even deeper, starting again with Correa after he opted out of his Twins deal.

Correa is followed — alphabetically, if not in appeal — by former National and Dodger Trea Turner. Turner loved the East Coast during his time with the Nationals, according to multiple people who speak to him regularly, and while he hasn’t ruled out a West Coast option, the sense is that he would prefer a team that trains near his offseason home in South Florida.

One team that trains in Florida, albeit across the state from where Turner grew up, is the Philadelphia Phillies, a team led by his former teammates Bryce Harper and Kyle Schwarber and hitting coach Kevin Long — a team that always seems to have money to spend and could use a high-profile shortstop.

Longtime Red Sox staple Xander Bogaerts is also on the market, and his agent, Scott Boras, jumped into the speculation dialogue this week to correct any notion that Bogaerts was considering signing with a team that would move him to second base.

Atlanta Braves shortstop Dansby Swanson is a free agent, too. He is a less productive offensive player than the rest, though he has a more formidable defensive presence. His situation is complicated by the fact that a) the Braves have shown a recent history of extending stars they want to keep long before they hit free agency and b) Swanson’s agency, Excel, was the one that engaged in a contentious negotiation with Atlanta’s front office just last season when another client, Freddie Freeman, hit the market.

How high can the cost of starting pitching climb?

Of all the sectors of the free agent market so far, the most active has been the starting pitching market, and the early returns bode well for the handful of starters at the top of this year’s class. Aces such as Verlander and deGrom watched as far less-decorated starters have earned substantial contracts, from $10 million for Detroit Tigers starter Matthew Boyd (whom the Tigers non-tendered this season) to the Los Angeles Angels giving $39 million over three years to 31-year-old right-hander Tyler Anderson to the Tampa Bay Rays giving their biggest free agent contract in franchise history (three years and $40 million, per reports) to … Zach Eflin, owner of a 4.49 ERA over 127 career outings.

Then deGrom blasted by all comers when he agreed to a five-year deal reportedly worth $185 million, or $37 million annually — the second-most money guaranteed to a player on an annual basis in major league history.

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Because of his age, the 39-year-old Verlander always seemed likely to entice more teams on a short-term, high-annual-value deal like the one Max Scherzer got from the Mets last year. He is the kind of ace a win-now team could count on to give it a couple more solid years, making reports of his meetings with the Dodgers and Yankees seem all the more logical. After seeing what deGrom got annually for a fairly long deal, Verlander might just find himself challenging Scherzer for the biggest annual payday in major league history.

Will Bonds and Clemens punch tickets to Cooperstown?

The first of these questions to be answered may be that of whether accused steroid users Barry Bonds and Roger Clemens will finally make their way into the Hall of Fame. The voters in the Baseball Writers Association of America rejected their candidacies for good last year when they did not choose either man in his final year of eligibility for the ballot.

But for the first time, in accordance with a new Hall of Fame system, the Contemporary Baseball Era Players Committee — a group of 16 former players, current executives and longtime media members — will meet to vote on the candidacies of eight players who made their mark in the years since 1980 but were not voted in by the writers. The eight players on their ballot are Bonds, Clemens, Curt Schilling, Fred McGriff, Rafael Palmeiro, Albert Belle, Don Mattingly and Dale Murphy. Those who receive votes on at least 75 percent (or 12 of 16) committee ballots will be elected for induction in 2023.