Will A Bernie Williams-Esque Last-Second Deal Be Enough To Make Aaron Judge This Era’s Derek Jeter?

The defining moment in Aaron Judge’s metamorphosis into the Yankees’ next generation version of Derek Jeter might have happened Friday, when Judge and the Yankees avoided a contentious showdown in a fashion reminiscent of Bernie Williams and the Yankees dodging a divorce at the last moment almost a quarter-century ago.

There is, of course, a decidedly more than non-zero chance the preceding paragraph ends up as fodder for Cold Takes Exposed this winter, when Judge is going to hit free agency off what is shaping up to be a historic contract push.

But the months-long game of chicken between Judge and the Yankees ending without the two sides potentially damaging the relationship beyond repair Friday — when Judge agreed to a one-year, $19 million deal with incentives moments before an arbitration hearing was scheduled to begin — evoked memories of Williams’ last-second reunion with the Yankees following the 1998 season.

Williams’ dalliance with the Red Sox happened during his free agency courtship, when the Yankees flirted with Albert Belle and Williams was on the verge of signing a deal with his club’s bitter arch-rivals. On the morning of Nov. 24, 1998, an article titled “For Yanks It’s Plan B, As In Belle” appeared in the New York TimesNYT
. The next morning’s headline was even more foreboding: “Williams and Yankees Near a Final Separation.”

But Williams requested one more in-person meeting that day with Yankees owner George Steinbrenner, who hadn’t budged off his offer of a five-year, $60 million contract. Hours later, shortly after sunset on Thanksgiving Eve, the Yankees announced they’d signed Williams to a seven-year deal worth $87.5 million. Williams batted .296 with 161 homers, 691 RBIs and an OPS of .857 over the final eight seasons of his career (he finished with a one-year deal in 2006) before getting his number retired and earning a plaque in Monument Park in 2015.

No matter how contentious things could have gotten Friday, Judge was still going to finish the season with the Yankees and not jump to their most bitter rival. But it’s not hard to envision a scenario in which an unusual in-season hearing — necessitated because the owners’ lockout wiped out the off-season calendar — shattered the union between Judge and the Yankees with a finality on par with a franchise icon signing with the Red Sox.

Judge was unhappy after negotiations on a long-term extension fizzled in the spring and Yankees general manager Brian Cashman revealed his “final” offer, a seven-year deal worth $213 million, hours before Opening Day. Imagine how those feelings could have been compounded if the Yankees spent hours explaining why they should pay Judge — on pace to hit 62 homers, one more than Roger Maris’ team record, for a squad on pace to win an all-time record 119 games — $17 million instead of the $21 million he requested.

With that in mind, Cashman and Hal Steinbrenner blinking at the last second — minutes before the settlement news linked, ESPN reported Judge declined an offer to agree at the midway point — just as George Steinbrenner did in 1998 could provide the polish that smoothes over any difficulties the Yankees had with the superstar over the course of the latter’s career. The Yankees went to arbitration once apiece with Jeter and Don Mattingly and twice with Mariano Rivera.

Perhaps 15 or 20 years from now, only a scattered few will remember the quirky awkwardness of the 2021 season when Judge is solidified as a “Yankee for life” — the phrase he used in spring training and the same words Jeter uttered regarding his hopes following the 2000 season — upon his 99 being retired and his monument erected.

Then again, maybe not. Judge isn’t just Jeter’s potential heir in terms of status within the franchise. He’s also the modern version of Jeter in terms of comportment — measured, cool and distant, with a long memory when he feels he’s been slighted.

And in a very Jeter-esque way, Judge made it clear Friday night he didn’t like that the hearing came so close to happening, or that it likely would have cost him a chance to play against the Astros.

“We had it scheduled, I think, for 12 o’clock,” Judge said. “I don’t know who picked that, but bad timing on that.”

Judge also admitted he wondered why the Yankees couldn’t have met him in the middle months ago and twice said this agreement wouldn’t persuade him to change his mind regarding negotiating an extension during the season.

“That’s for when the season’s done,” Judge said, letting the Yankees know — in an unblinking way Jeter would surely admire — the big showdown is still to come.