Yankees insiders battle over team’s ‘confidence’ in bringing Aaron Judge back

MILWAUKEE, WISCONSIN - SEPTEMBER 18: A detailed picture of the Franklin batting gloves worn by Aaron Judge #99 of the New York Yankees against the Milwaukee Brewers at American Family Field on September 18, 2022 in Milwaukee, Wisconsin. (Photo by John Fisher/Getty Images)
MILWAUKEE, WISCONSIN - SEPTEMBER 18: A detailed picture of the Franklin batting gloves worn by Aaron Judge #99 of the New York Yankees against the Milwaukee Brewers at American Family Field on September 18, 2022 in Milwaukee, Wisconsin. (Photo by John Fisher/Getty Images)

The Yankees Word of the Day Monday night was “confidence,” though reporters couldn’t decide whether the team lacked it or possessed it in abundance. Yeah, feels like “One Week Before the Winter Meetings” for sure.

Aaron Judge’s free agency saga began “in earnest” the week of Thanksgiving, though it was difficult to discern reality from pageantry. After all, his arrival in San Francisco was leaked immediately to Jon Morosi in a video message where he winked at the idea of “big plans.”

The coordinated media push ratcheted up the perceived pressure on the Yankees, but that was the point, after all. With so few teams involved in the sweepstakes, the more serious Judge can convey San Francisco’s interest, the better.

Which brings us to the week prior to the Winter Meetings in San Diego, a time when baseball fans everywhere have been assured checks will be flying and Scott Boras will be pumping his fist like Leo in “Wolf of Wall Street” on the trading floor. Judge is rumored to want to finish this saga off quickly, though FanSided’s insider Robert Murray isn’t so sure on the speed.

In assessing the circumstances — again, which include only Yankees and Giants meetings, plus a bogus leaked Dodgers “offer” — SNY’s Andy Martino cautioned fans against becoming too optimistic in the Yankees’ chances. In fact, he called the team “hopeful” about retaining Judge, claiming “confident” went too far.

Yankees ‘confident’ in signing Aaron Judge, per Jack Curry. Yankees not ‘confident’ in signing Judge, per Andy Martino.

Martino’s report feels a bit more dire than the other discourse we’ve heard lately. After all, “hope” is what you sell success-starved fans. “Hope” is a wish, a dream. “Hope” doesn’t project … well, confidence.

Just a few hours later, though, YES Network’s Jack Curry — arguably the Yankees’ most plugged-in source, and probably the favorite in the clubhouse (literally) to break an eventual Judge signing — played the opposite card.

He claimed that not only does he perceive the Yankees as confident in this chase, but he stated he knows they’re confident. He even added a “comfortable” modifier and some estimated contract terms for good measure.

And when Jack Curry estimates contract terms, you’d better believe those are pretty close to the real contract terms.

At this point, the only thing we’re “confident” in is that, if the Yankees don’t sign Judge, Hal Steinbrenner will look like a maxed-out fool after declaring the team would not be outbid for his services.

It seems more likely than not that the Yankees and Judge eventually continue this marriage, elevating No. 99 to the captaincy and pledging to build around him (maybe next year … yeah, someday, definitely …). Anthony Rizzo’s return is certainly a reason to feel that famous “confidence,” when push comes to shove.

Hopefully, at the Winter Meetings, the beat writer battle over Judge turns from a war of semantics to a chase for the Yankees’ contract details. Expect Curry to win that one, too.