The story of the Winter Meetings is the same almost every December: Pressure.

The conversations at this annual industry-wide convention, which will take place for the first time since 2019 in San Diego this week, often revolve around money. But the forces driving the spending — the reason wallets open up and record-setting free-agent deals get made — take different shapes. The pressure can come from the ownership above or the clubhouse below. It can come from an internal desire to jumpstart a rebuilding effort, or from an external concern about fans refusing to line up at the box office. It can come from the fear of missing out on an exceptional talent — the sort that might not come along again soon.

Several players fit that description this winter. Jacob deGrom, the two-time Cy Young Award winner, has already made his decision, departing the Mets for a five-year, $185 million contract from the Texas Rangers. He won’t be the last star to cash in.

Aaron Judge authored the finest platform season in recent memory. Justin Verlander returned from major surgery to win the World Series and his third Cy Young Award. Carlos Correa, Trea Turner and Xander Bogaerts are three of the best shortstops in the sport — and Dansby Swanson wasn’t far behind in 2022.

Yet even the players are not immune to the pressure. The forces can cut both ways. There is pressure to find the right landing spot, pressure to surpass prior deals. For certain agents, there is pressure to live up to their lofty rhetoric.

As a way of understanding what will transpire this coming week in San Diego, we present to you a list of the owners, executives, agents and players facing the most pressure at the Winter Meetings. The story of this week will be told through how they react to it.


Hal Steinbrenner, Yankees owner




You guessed it. For Steinbrenner and the Yankees, this entire winter boils down to the franchise’s ability to keep Judge in pinstripes. Steinbrenner said a few weeks ago he wants to make Judge “a Yankee for the rest of his life.” It will surely cost more than the $213.5 million offered by the Yankees at the outset of the season. But Steinbrenner and his ownership group can afford it, even if Judge surpasses Mike Trout’s record for average annual value for a position player at $35.5 million.

The bigger question, really, is if Steinbrenner can afford to let Judge leave.

The Yankees could survive without him. You could make an argument, from an actuarial perspective, that signing up for nearly a decade with an oversized outfielder entering his 30s may be a mistake. But that ignores all the potential benefits, both in marketing the franchise away from the diamond and winning games on it, that could accrue from a partnership with Judge.

Steinbrenner understands as much, which is why many executives within the industry view the Yankees as the favorite to win the bidding. The Yankees are a financial behemoth, but the team often resides on the periphery of free-agent sweepstakes. When necessary, as with Aroldis Chapman and Gerrit Cole in the past, Steinbrenner is willing to set records for spending. A deal with Judge may require that.

“We have plenty of ability to make other things happen too,” Steinbrenner also said earlier this month. It is a nice sentiment. But it is hard to imagine his fanbase, already howling about stagnation amid the 13-year World Series drought, taking things well if the Yankees permit Judge to depart.