Aaron Judge’s Contract Negotiations Will Likely Be Main Event Of Frenzied Winter Meetings

Normally the first Sunday of December finds Brian Cashman scaling down Stamford’s Landmark Building in an elf costume, something he did almost every year since 2010 until opting not to participate this time around.

Maybe because he did not want to face an inquiring media, whose lone purpose to stand out in the cold for the event is to ask Cashman questions ahead of a flight to the winter meetings. Or maybe because he realizes how critical the negotiations are for retaining Aaron Judge will be and needs to prepare.

There’s a reported eight-year, $300 million deal the Yankees apparently made which is a sizable increase from the $213.5 million offer they announced to the public on April 8 before his 62-homer season began. All indications seem to be it will take more than $300 million and possibly somewhere closer to $400 million with a deal likely being nine years in length from either the Yankees, Giants or possibly some other team.

And based on the annual value of Jacob deGrom’s new contract with Texas standing at $37 million, it seems reasonable to think Judge will seek more considering his nearly daily availability as opposed to deGrom’s two months of dominance.

The last time $400 million was thrown around in baseball circles occurred around the All-Star break was when Juan Soto rejected the $440 million offer from the Nationals. Two weeks later he was traded to the Padres, who now face the same scenario as the Yankees next season and at the time heading into the 2023 winter meetings should a deal not get done.

As of now, the highest contracts by total value are the 13-year, $330 million deal signed by Bryce Harper with Philadelphia following the 2018 season and the 10-year, $325 million contract Corey Seager inked with Texas last year where he now be a teammate with $185 million man Jacob deGrom, whose worth is being hotly debated in New York given the fact he won five games and pitched fewer innings than Edwin Diaz for the Mets.

The Yankees currently hold the distinction of agreeing to the third-largest contract in baseball history when the added Gerrit Cole on a nine-year, $324 million deal. Coincidentally it was in San Diego, where this year’s meetings are being held, so maybe it’s a good omen for the Yankees retaining Judge if you believe in such things.

In the past, the Yankees have gotten their free agents when they’ve really wanted them. They really wanted to re-sign Bernie Williams following the 1998 season in negotiations that became too stressful for fans and nearly resulted in the undesirable scenario of the beloved center fielder playing for the Red Sox and the Yankees pivoted to Albert Belle.

Three years before Williams, the Yankees really wanted to retain David Cone, whom they acquired in the middle of 1995 to stabilize a physically battered rotation. Cone was re-signed but only after the Orioles swooped in with an offer and became a key component of four title teams, even getting the biggest out of Game 4 of the World Series when he retired Mike Piazza after relieving a peeved Denny Neagle.

Nine years ago, the Yankees did not seem willing to go and above beyond what it took to retain Robinson Cano. Instead of returning on a deal worth about $170 to 180 million, Cano went to Seattle grew a beard and accepted a $240 million deal that did not work out due to his two PED suspensions in 2018 and 2021.

The Yankees seemed ambivalent about retaining Cano, perhaps swayed by his not hitting in the 2012 ALCS or did not see the value in the back end of such long contracts.

Either way, they survived not retaining Cano, though Judge certainly had something to do with it since his arrival on the scene on Aug. 13, 2016 and subsequent 52-homer breakout in 2017.

And because of what Judge did last year, his contract talks, and possible announcement of a new deal will be the biggest attraction at the transaction festival known as the winter meetings with fans feeling the anticipation and disappointment depending on what teams lands the biggest free agent of the year.

Until then the world will be watching Brian Cashman and Hal Steinbrenner, whom a large segment of fans are annoyed at as evidenced by them being booed at the Paul O’Neill retirement ceremony in August and the negative reactions of Cashman’s 45-minute post-mortem press conference a month ago.