BENEATH THE PINSTRIPED No. 99 uniform, behind the home runs and the good-natured smile and the perfect soundbites emitted day after day during Aaron Judge‘s historic season, New York Yankees staffers knew he harbored at least some anger. But they did not know the depth of his resentment, which came spilling out last week as Judge neared a decision about whether to return to the Bronx. That timing was one more plot twist, after weeks and months of uncertainty.
On the eve of the 2022 campaign, the Yankees had offered Judge $213.5 million over seven years, a deal that would’ve made him the second-highest-paid outfielder in the majors, behind Mike Trout. To club executives around baseball, and even to some agents and union staffers, it was a fair offer for a player who will turn 31 in April.
Judge, just seven months from free agency, turned down the proposal. Yankees general manager Brian Cashman then outlined the offer for reporters in the Yankee Stadium press room, citing the reality that the numbers would inevitably emerge through anonymous sources. Later that same day, Judge indicated to reporters he was displeased with Cashman’s revelation but didn’t really elaborate.
Last week, however, as baseball’s winter meetings began in San Diego with everyone wondering where Judge would sign, Time magazine — which named Judge its Athlete of the Year — published an interview with the slugger, in which Judge revisited the spring negotiations. “We kind of said, ‘Hey, let’s keep this between us,'” Judge told the magazine. “I was a little upset that the numbers came out. I understand it’s a negotiation tactic. Put pressure on me. Turn the fans against me, turn the media on me. That part of it I didn’t like.”
At a time when the Yankees were trying to convince Judge to come back, his now-publicly stated offense at the circumstances landed hard in the Yankees’ suite of club officials.
“I had that feeling that we were going to lose him,” said a Yankees official, one of some two dozen industry sources interviewed about Judge’s negotiations with both New York teams and with his other top suitors — the San Francisco Giants and San Diego Padres — and others around MLB.
In the end, Judge elected to return to the Yankees on a nine-year, $360 million deal that all but ensures he’ll finish his career with the team that drafted him. Soon, the contract will become official, and he’ll be reintroduced at a Yankee Stadium news conference.
And looking back, it would be easy to say that the rival executives who consistently predicted that Yankees owner Hal Steinbrenner would never let one of the game’s most prominent superstars get away were right all along. But that’s not how it felt to those involved in the talks.
As it turned out, Judge’s stoic personality served as negotiating leverage. Judge was the poker player who stayed on point, never changed expression and rarely betrayed emotions — and in the end, he won big.
IN THE MIDDLE of the summer, Charlie Kay, the 7-year-old son of Yankees broadcaster Michael Kay, informed his father that if Judge departed then his allegiance to the team would end. Michael Kay followed up: You’d stop rooting for the Yankees even though your dad does play-by-play for the team? Charlie was resolute: Yes.
The broadcaster approached Judge later that day to relate that story, and what he saw flash across Judge’s face was sincere pain. And Judge responded: “Please tell Charlie not to worry.”
Kay might have been the only person in the Yankees’ universe who had a hint of what Judge might want, because Judge’s public handling of the situation was inscrutable. He deftly deflected questions about his impending free agency, reflexively pivoting to talk about the team. He never publicly complained, never personally called attention to himself — and day after day, Judge performed on the field, his perceived value climbing as he approached then surpassed Yankees legend Roger Maris’ single-season American League home run record.
Yankees manager Aaron Boone had predicted in the first weekend of the season that Judge would handle the forthcoming scrutiny of his walk year, but Judge’s ability to compartmentalize his contract situation — his mental strength — went above and beyond what some club officials had ever witnessed from other players. “I don’t think you could’ve had a more perfect response,” one staffer said. “He did everything the right way.”
At the end of a disappointing AL Championship Series, when Judge was booed by Yankees fans during a 1 for 16 performance, a staffer spoke with Judge about how much the team wanted to bring him back. He told the slugger that the franchise intended to do everything it could to retain him. In conversation, however, Judge was noncommittal. After the World Series, he moved off the Yankees’ roster and into free agency.
When Judge turned down the Yankees’ spring proposal, his side had presented no counteroffer, no tangible financial bar at which the team might aim. Just: No. There were no conversations about a long-term deal during the season, no revisitation of negotiations, not even when the Yankees and Judge haggled over his arbitration case at midseason.
Through any of those interactions, with Cashman and others, the slugger had never complained about the GM defining the Yankees’ offer for reporters. Rather, Judge was as genial, uniformly, even as the two sides moved toward their next round of negotiations.
Cashman also encouraged Steinbrenner to get involved in the talks directly. With so much money involved and the offers potentially rocketing upward, a general manager is going to be a conduit, a middleman. Steinbrenner had the power to significantly increase the team’s offer in an instant, if necessary.
There were two meetings in Florida after the playoffs between Steinbrenner and the player, and the Yankees dangled their first enhanced offer: $300 million over eight years, or an average of $37.5 million annually, slightly more than Trout’s deal. Later, that offer would climb to $320 million, or $40 million annually.
But on the eve of Judge’s decision, when the quotes to Time magazine were released, the Yankees were shocked by Judge’s obvious frustration; they felt the issue had been put to bed months before. As Cashman presented the spring offer, club sources say, he told Judge’s agent, Page Odle, that regardless of whether Judge accepted or rejected the offer, he intended to reveal the proposal so that the team’s fans would know the Yankees made an earnest attempt to keep the slugger. Whether Odle has a different recollection is not known; the agent did not respond to three messages.
Nine months later, Yankees officials weren’t sure whether to translate Judge’s pointed words as a first sign of what he might really feel, of what he might really want. They had selected Judge with the fifth pick of the compensatory round of the 2013 draft, the team’s second selection and the 32nd pick overall, and after nearly a decade with the organization, there was sweeping respect for him as a player and a person. But they didn’t really have a sense of whether he wanted to stay or go.
That was the common denominator for all teams in trying to assess the Judge sweepstakes: They really had no sense of what he wanted. Was it money? Was there a draw to his home state of California? It was unclear — but plenty of teams were willing to try to find out.
EARLY IN THE offseason, the Los Angeles Dodgers were linked in reports to the Judge bidding, but they were never involved — and, in fact, didn’t even meet with Judge’s agent at the general managers meetings in early November. Neither did the Chicago Cubs, another big-market team that focused elsewhere.
The New York Mets discussed Judge in their internal evaluations, as they prepared for the offseason, and met with Odle at the GM meetings. But they informed Judge’s representative that their offseason priority would be the pursuit of starting pitching — and if those holes were addressed and Judge was still unsigned, the two sides might pick up those threads. But the expectation within the Mets organization after the GM meetings was that Judge would be off the board by the time the rotation was filled; and generally, that’s how it played out, as Justin Verlander agreed to terms with the Mets a couple of days before Judge signed, and the Mets subsequently signed veterans Jose Quintana and Kodai Senga.
The Giants, on the other hand, were serious about pursuing Judge, who had grown up a fan of the team in Linden, California, about 100 miles from Oracle Park. But even as they prepared to bid, there was a lot of skepticism in the organization about whether Judge would actually leave the Yankees — and whether the Yankees would allow themselves to be outbid. “A long shot,” said one official, on the eve of the offseason. “He’s going back to the Yankees, don’t you think?”
But the Giants had almost no long-term payroll obligations, a need for a masher in the middle of their lineup and, since the retirement of Buster Posey, no one who could serve as the face of the franchise. Despite the doubts about whether they could actually pry Judge away from the Yankees, the Giants forged ahead, projecting two possible scenarios that could result in Judge landing in San Francisco: Maybe the Yankees, who had historically held the line in negotiations with many great players, would remain financially disciplined and hold to their offer in the spring; or perhaps Judge privately wanted to realize a childhood dream of playing with the Giants.
Although Judge’s impending arrival at Oracle Park in the days before Thanksgiving had been reported, the Giants kept the details of his movements away from a lot of club employees. Rich Aurilia, who had been Judge’s favorite player as a kid, was brought in to greet the slugger. Giants officials presented the organization and its rich history, and the club officials who participated listened — largely trying to ascertain whether he was actually considering leaving the Yankees — and came away deeply impressed by Judge and his wife, Samantha Bracksieck, and by the player’s earnest dignity. One official was struck by Judge’s manner of responding to questions: He always pauses before his answers, seemingly to think about his words, to measure them and weigh their impact. For his part, Judge asked questions about the team’s facilities, spring training site and resources.
One source said the Giants’ offer to Judge went to $360 million; another said it was at $320 million. Either way, their interest was serious, creating a legitimate alternative to the Yankees. And the meeting ended with the Giants feeling that Judge would sincerely weigh their offer, not just use it to push the Yankees into a higher offer.
They believed they had a shot as Judge left San Francisco in late November. And with the winter meetings only a few days away, many around baseball believed that Judge would be ready to make a franchise-altering decision in San Diego.
IN THE MIDDLE of the afternoon on Dec. 6, Boone was getting dressed for a scheduled round of media availability, but that was interrupted by a one-word text from someone else in the Yankees organization:
“F—.”
It didn’t take Boone long to ascertain the context for that frustration. The New York Post’s Jon Heyman had tweeted this:
“Arson Judge appears headed to the Giants.”
In the Yankees’ suite, initially there was mostly just uncertainty about what this meant. Cashman, who will soon enter his 25th year as the team’s GM, has experience dealing with the free-agency rumor mill — and as another official noted, that experience manifested in that moment. Cashman knew better than to overreact to a report that might well turn out to be wrong.
Somebody pointed out that the post came from a verified Twitter account, not an imitator. There was some chuckling over the typo “Arson,” the built-in double entendre for any team that didn’t get Judge. But as they awaited confirmation or denial from the player or his agent, a club official pulled up a movie scene on his cell phone — that dire moment in “Apollo 13” when flight director Gene Kranz, played by Ed Harris, tells a panicked staff, “This is going to be our finest hour.”
In fact, corrections were already being rendered. Cashman called Odle, Judge’s agent, who told him that the information in the tweet was incorrect. Farhan Zaidi, San Francisco’s head of baseball ops, contacted Heyman to inform him, in so many words, that if Judge was headed to the Giants, the Giants knew nothing about it.
Someone with one of the teams involved with the Judge bidding noted the exact timing: Seven minutes after Heyman’s tweet ignited social media, the post was deleted. He followed with a retraction shortly after.
But with the bidding teams on edge, and with hundreds of representatives from the industry gathered at the winter meetings, the tweet still had a palpable impact — and Boone was scheduled to speak to reporters within an hour of its emergence.
“I know nothing,” Boone said to open his availability. “I really don’t. It’s been an uncomfortable hour.”
The Yankees’ strategy for the offseason, laid out over weeks in Zoom calls and meetings, was built around retaining Judge. They had discussed Plan B’s, many of which included diving into the rich shortstop market, but there was no projected lineup that didn’t include the player who had broken the AL record for homers. And in those hours, there was real concern that he was going to go someplace else — and maybe even another California team, not the one that everyone was expecting.
At the general managers meetings, agents sensed the Padres were prepared to spend whatever necessary to improve a team that already has expensive stars Manny Machado, Juan Soto and Fernando Tatis Jr. San Diego first pursued shortstop Trea Turner, with chairman Peter Seidler, GM A.J. Preller and others traveling across the country to meet with him; the Padres had drafted and signed Turner out of college before trading him to the Washington Nationals. The Padres offered Turner what would have been a record-setting deal for a shortstop — $342 million — while implying that if Turner needed more to make the deal happen, they were prepared to give it to him.
When Turner chose to take less money from the Philadelphia Phillies, the Padres turned to Judge, inviting him to a meeting in San Diego. On Dec. 5, Judge attended a Tampa Bay Buccaneers home football game then told a friend he was going to fly to San Diego to talk with the Padres. As news leaked — and as Yankees officials stated that they knew nothing about the meetings or Judge’s visit — the Padres tried to move as stealthily as possible; rather than host Judge in the team’s offices, Preller held the gathering in the GM’s private suite at Petco Park on the evening of Dec. 6.The Padres assured Judge that the franchise would sustain a significant payroll and not go through the peak-and-valley spending cycles commonplace for teams of smaller markets. Padres officials were as impressed by Judge as the Giants were, and similarly, they thought Judge was open to the idea of leaving the Yankees.
San Diego floated contractual concepts, with a functional bottom line: The Padres were prepared to commit more dollars than what Steinbrenner had on the table. The talks with San Diego never progressed to the degree that anything formal was presented to the league offices; according to league sources, a report that MLB would have rejected one of the contractual structures the Padres had discussed is not accurate.
While Judge met with the Padres, Boone was attending dinner with others in the Yankees organization. Judge’s looming decision was on everyone’s mind, and the manager asked the others at the table whether he should call Judge one last time. The vote in the group seemed to be unanimous: Yes, call him. At this stage, what did the Yankees have to lose? Boone dialed.
He reiterated how much the Yankees wanted him, and he was “hopeful” after the call, Boone said the next day. Later that night, he would relate to others that Judge had seemed a little down; he hadn’t made a final decision.
By the end of Dec. 6, Judge seemingly had three great, distinct choices. If he wanted to play for the favorite team of his childhood, he could sign with the Giants. If he wanted money, the Padres would provide him with the most guaranteed dollars. And if he preferred legacy, staying with the Yankees, that was available to him.
The baseball world awaited his choice.
GEORGE STEINBRENNER BELIEVED strongly in the marketability of stars, in marquee value — and he spent aggressively, sometimes impetuously, to bring stars to New York. His son Hal has run the Yankees with a more circumspect manner, always carrying one of the highest payrolls in baseball but maintaining discipline. The Yankees allowed Robinson Cano to walk away as a free agent, and Steinbrenner has sometimes approved of Cashman’s advice to dip under the luxury tax threshold.
But a high-ranking executive with another club — someone who is a friend to Steinbrenner — noted earlier this month that the business of baseball has rapidly evolved. There are far more revenue sources than there were in George’s day, and a star of Judge’s transcendence possesses almost incalculable value to the Yankees beyond TV ratings or tickets sold. The Yankees had no choice but to give Judge whatever was needed to complete the signing, the executive said. Given the fans’ collective investment in the team, the booing that Steinbrenner had borne during a ceremony at Yankee Stadium during the year might become habitual.
On Boone’s advice, Judge called Steinbrenner, on vacation in Italy, on the night of Dec. 6. Though Steinbrenner had spoken to the player often throughout the offseason, the Yankees owner knew this might be the last chance he had to make his case.
According to sources, he asked Judge the question that vexed club executives all season and through the first five weeks of free agency: Did he want to be a Yankee?
Yes, Judge indicated in so many words, he wanted to play for the Yankees.
With that assurance in hand, Steinbrenner increased the Yankees’ offer, which had stood at $320 million, to nine years and $360 million. Judge accepted. In Italy, it was lunchtime; 6:30 in the morning on the East Coast. As Cashman waited sleeplessly in San Diego, it was 3:30 a.m. when Steinbrenner called to tell him that Judge had agreed to terms.
Little more than an hour later, news of the agreement broke. A one-word text from a friend woke Boone: “Congrats.” Boone immediately reached out to Cashman and asked, “Is this real?”
Cashman acknowledged that it was. The baseball world — including the executives from the Padres and Giants — woke up to the tweets and texts that Judge was returning to the Yankees.
“Hal Steinbrenner has been the tip of the spear with this one,” Cashman told reporters a few hours later. “Our organization has tried to stay connected in every way possible — Hal Steinbrenner directly with Aaron Judge, as well — to make sure that there was going to be no stone unturned and there was no effort missed in our discussions.”
All that is needed to make the deal official is for Judge to take the full physical examination prescribed when free agents are signed. Agents often encourage players to do this right away, to diminish the risk of some freak accident — like blowing out a knee in a pickup basketball game, as Boone had notably done in January 2004, igniting the Yankees’ pursuit of Alex Rodriguez.
But Aaron Judge — who had walked away from that Yankees offer in the spring and risked hundreds of millions of dollars, only to generate one of the greatest performances ever and pay off the enormous bet on himself — got on a plane with his wife to Hawaii, to celebrate their first anniversary. The medical review can wait. The Yankees can wait a little longer too — now, finally, that they know the star who almost got away will find his way back to New York.