When the clock struck three in the wee hours of a Hawaiian morning, Aaron Judge wasn’t dreaming of mai tais and luaus. He was on a mission. A direct line to New York Yankees owner Hal Steinbrenner, a heartfelt plea to stay in pinstripes, and boom—a nine-year deal with $40 million AAV—and the captaincy was his. The baseball world was left stunned—and rival GMs? Likely, fuming. Could this unprecedented 3 AM shocker be a sign of things to come for the Bombers’ other coveted soon-to-be free agent, Juan Soto?

“I’m telling her, like, ‘You know I want to stay in New York; I don’t want to go anywhere else,’” the All-Rise recounted of the conversation with his wife, Samantha, that led to the fateful call. “Conversations in New York really weren’t going anywhere; she’s like, ‘Just call them up, see, tell them how you’re feeling, tell them what you think,’ I was like, alright!” Leading the way to a raw, unfiltered exchange between a player and his partner that ultimately altered the course of Yankees history, proving that sometimes the most impactful negotiations happen outside the boardroom.

“So we call him; I’m just kind of laying it out—‘Hey, like, I want to be here; I don’t wanna go anywhere… You can just add one more year to the deal. I’m not looking for anything more.’ He’s like, ‘That’s it?’ Yeah, he’s like, ‘Alright, done, sounds good,’ like, dang! I should’ve asked for two more years, man!” Aaron Judge exclaims laughing, revealing the surprisingly simple conversation that sealed his fate in the Bronx, painting a picture of a refreshingly candid negotiation—one that’s devoid of the usual posturing, gamesmanship, and business jargon.

But the conversation didn’t end there. As the All-Rise recalls in the latest episode of “Casa De Klub,”  Steinbrenner then adds, “Oh, by the way… We’re also going to make you the next Yankee captain.” The unexpected offer of the captaincy, a title steeped in Yankees history, left Judge speechless and underscored the personal touch that Hal brings to the negotiations—a move that, statistically speaking, has only happened a handful of times in the franchise’s illustrious history. And the rest—as baseball fans are witnessing around the world—became history in the making.

Steinbrenner’s hands-on approach with Aaron Judge, bypassing agents and GM Brian Cashman, signaled a new era in the Yankees’ free agency. Now, as the ’24-’25 period looms, could Soto be the next “unique” case where the owner takes the reins? As Hal himself said of the Childish Bambino, “This is a unique situation and a very unique player.” The old adage “actions speak louder than words” never rang truer.

Scott Boras, Soto’s agent, is notoriously tough with his negotiations, known for playing the field to extract maximum value. Remember Bryce Harper’s protracted free agency? Boras orchestrated a bidding war that lasted months and ultimately landed Harper a record-breaking 13-year, $330 million deal. “I never played the game to be that,” Judge reflected on the financial aspect, a stark contrast to Boras’ usual tactics. Maybe that’s the reason why he isn’t All-Rise’s agent. But when there’s an elephant in the room called money, therein lies the question of financial constraints.

Juan Soto’s $440 million question: Will Hal Steinbrenner break the bank for another generational talent like Aaron Judge?

This year, Hal Steinbrenner has cautioned about the unsustainability of the Bombers’ current payroll, which already exceeds $300 million, particularly after Juan Soto famously rejected a 15-year, $440 million extension from the Washington Nationals in 2022 before being traded by them to the San Diego Padres. Would the owner be willing to break the bank for Soto, especially if it means keeping him away from rivals like the New York Mets?

“We all know he’s generational, right?” Steinbrenner was found remarking on one of YES Network’s Jack Curry podcasts this year. “He’s the complete package.” This admiration for the Bambino’s skills and character could be the key to unlocking a deal, even amidst financial constraints. Because, let’s face it, a generational talent demands a generational contract.

While the Mets and Los Angeles Dodgers lurk as potential suitors, the slugger’s recent comments suggest a preference for staying in New York. “My door’s always open,” he quipped. “Whenever he [Steinbrenner] wants to start talking, they’re always open to hear whatever he has to say”—a statement that feels less like a negotiation tactic and more like a heartfelt invitation.

The Yankees’ front office faces a crucial decision. Will they follow the blueprint laid out by Judge’s dramatic signing, or will traditional negotiating norms prevail? The ripple effects of this decision could extend far beyond the Bronx. As the captain himself expressed gratitude for the opportunity to wear pinstripes—“It’s pretty surreal, that’s for sure.” If Steinbrenner can tap into that same sentiment with Soto, his team could secure another long-term commitment from a familiar franchise-altering talent.

The Aaron Judge saga taught us that anything is possible in the world of baseball. If a midnight phone call can secure a captain and a franchise cornerstone, who’s to say it can’t also land another superstar outfielder? As the legendary Yogi Berra once said, “It ain’t over ’til it’s over.” The verdict on Hal Steinbrenner’s audacious strategy will unfold over time, etched into the annals of Yankee lore. This much is undeniable: the Hot Stove is already burning bright, and this offseason promises to be a scorcher.