Three years ago, in an offseason that Yankees general manager Hal Steinbrenner made clear he intended to spend in free agency, the Winter Meetings were held at the Manchester Grand Hyatt in San Diego.
The Yankees walked away from those meetings with a nine-year, $324 million contract for Gerrit Cole, the best pitcher on the market.
This week, with the Winter Meetings in the same hotel, Steinbrenner focused on a similar — and more specific — Aaron Judge.
And that’s how it ended, with Steinbrenner increasing the existing offer to keep Judge with the Yankees for one more year at the same annual salary.
Two years before Cole’s signing, the Yankees traded Giancarlo Stanton to the Orlando Winter Meetings for $265 million of the contract he signed with the Marlins.

Judge, Cole and, to a lesser extent, Stanton will now be linked for the rest of their careers, which will almost certainly end in the Bronx.
Now they just need to win. And the sooner the better.
Umpire, who will turn 31 in April, is coming off a season that led the majors with a 11.4 WAR per Fangraphs formula. It was a number he had previously approached as a rookie in 2017, when he put up 8.7 fWAR.
Cole had a 7.5 WAR in his final season in Houston before reaching free agency.
After the 2020 season was affected by COVID, that number dropped to 5.2 in 2021 and 3.3 last season.
Cole, 32, led the team in base hits (257) and starts (33) last season, but he also gave up an AL-high 33 home runs.
While there are concerns around the league about how Cole and Judge’s contracts will age, there’s no guarantee they’ll be as productive as they were in their walk years.

Judge probably won’t challenge his American League record again, and Cole probably won’t reach his 326 hits with the Astros in 2018.
But at the end of the winter meetings this week, shortly after news of Umpire’s contract broke, one agent said that Umpire’s most important hit this year was 157. It was the highest number of games played in his career. a career-high 696 plate appearances. Staying healthy allowed Judge to hit 62 homers, making him indispensable to Steinbrenner.
Can it remain this durable in 2023 and beyond?
Judge has often been compared to the similarly massive Stanton, who was traded to the Yankees in 2017 after exercising his no-trade clause to reject a deal with the Giants after his NL MVP season, the same team Judge refused to return to the Bronx.
Since being traded from the Marlins to the Yankees, Stanton has played at least 110 games once and has often been limited to DH when available.
The Yankees may suffer a similar fate with Judge.

But none of that matters if Judge, Stanton and Cole lead the Yankees to their 28th World Series title and first since 2009.
Closing time
Although Cole and Judge were under the same contract gun, the way the Yankees pursued each was very different.
After Cole agreed to his deal, he credited visiting Yankees clubhouse manager Lou Cucuzza with a bottle of Cole’s favorite wine to land him in the team area.
There was no magic bottle like the $900 bottle of Masseto Merlot that Cole got for the judge.
“Not this time,” Cucuzza said at the winter meetings this week. “It was all Hal.”
The only way to keep this umpire would be for Hal Steinbrenner to match the Giants’ nine-year, $360 million offer.

As general manager Brian Cashman pointed out Wednesday, having your own free agent is a lot different than going after a player you don’t have on your team.
Cashman pointed to teams bringing in local celebrities to lure a player and get them off the “red carpet.” But Judge probably won’t be impressed by any franchise he’s spent his entire career with.
“Other teams are recruiting big time,” Cashman said. “We can’t match that.”
So while everyone but the cast of “Full House” in San Francisco wanted to lure Judge back to the Bay Area, the Yankees had to hope that his experience with the team was good enough to want him to stay.
And as Cashman noted, “the biggest thing is going to be the contract.”
A lesson in leadership

All signs point to Judge being the next Yankees captain, the first since Derek Jeter resigned.
CC Sabathia, who played with Jeter and the umpire, said no such move was necessary.
“He’s already the captain,” Sabathia told Sports+. “I was there when Derek left. [Brett Gardner] became the unofficial captain. “We didn’t need him to have the title.”
After Judge established himself as the team’s leader, Sabathia said the same was true of the right fielder.
“Judge is the captain by default,” Sabathia said. “It doesn’t make sense to say his name at the moment. He already is. If you give it to him, nothing will change, why are you doing this?”
Cashman said the decision will be up to Steinbrenner this week, though the GM didn’t dispute that after saying Jeter should be the Yankees’ last captain.
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