1. Contract for Aaron Judge by Conclusion of Winter Meetings
When the Yankees want or need a player, they get said player. Regardless if it’s Hal or George. Hal’s just more conservative in his overall spending/bidding. The man paid a stupid $324 million for Gerrit Cole because he needed an ace. He knew he overpaid. The world knew he overpaid. But he did it. Because it was needed.
Judge is needed. Far more than Cole. Far more than anybody else in modern day Yankees history. If the Yankees lose him, they’re back to the drawing board. Without him, they miss the playoffs in 2021 and probably lose the division in 2022. This team is flawed with Judge, so imagine life without him? Now that’s something Cashman and Steinbrenner wouldn’t be able to stomach.
Multiple MLB insiders have suggested Judge will probably sign a deal at or shortly after the Winter Meetings. ESPN’s Jeff Passan said “all signs point to Judge returning” to the Yankees. He’s had a meeting with the San Francisco Giants and that’s it (at least of what’s been widely reported). If he’s going to leave the Yankees, it’ll be for a winning environment that can finish in October or an insane amount of money the Yankees would’ve never been willing to offer ($375 million? $400 million?).
Judge knows that if his free agency lags beyond the Winter Meetings, his price tag is more than likely going to decrease. He’s not going to want to be in a Bryce Harper or Manny Machado situation. The Yankees make the most sense. They always have.
Expect Cashman to make a few moves to round out the roster and then meet with Judge to settle this once and for all. If it doesn’t get done at the meetings, expect it shortly thereafter. Judge is a good guy. He wants this done before Christmas so Yankees fans can enjoy the holiday.
He is a man of faith, right?