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Will Aaron Judge Leave the Yankees as a Free Agent?

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Over the past six seasons, no player has been more synonymous with the Yankees, one of the biggest brands in all sports, than outfielder Aaron Judge.

In 2017, he won the American League Rookie of the Year Award and was the runner-up for the Most Valuable Player of the Year Award. He quickly became the face of the franchise and one of the biggest stars in Major League Baseball. He has been an All-Star four times, including this season, when he set an A.L. record with 62 home runs and carried the Yankees through their many ups and downs.

So it was only fitting that Judge came up to bat in the ninth inning on Sunday in Game 4 of the best-of-seven A.L. Championship Series with the Yankees trailing the Houston Astros, 6-5, and representing his team’s last hope. But even Judge couldn’t save the day.

Capping a disappointing postseason in which he hit .139, Judge swung at an outside pitch and produced a weak ground ball that Astros closer Ryan Pressly flipped to first baseman Yuli Gurriel for the final out. As the Astros began celebrating their fourth trip to the World Series in six years, Judge turned into the Yankee Stadium home dugout for what might have been his final time.

“Anybody that celebrates on that field, it’s not fun to watch,” he said late Sunday night while standing in a solemn Yankees clubhouse.

Now, the baseball world will watch as Judge’s future is decided. Five days after the World Series ends, Judge, 30, will be allowed to talk to any of M.L.B.’s 30 teams as a free agent for the first time in his career. The future of the Yankees — a franchise that loves to celebrate its winning tradition but hasn’t been to or won a World Series since 2009 — is intertwined with Judge’s.

“He’s a big part of this organization,” Yankees pitcher Nestor Cortes said. “This is the organization that drafted him, and he’s been here for a long time. He carries a lot of weight around here. He’s a superstar.”

“The money he’s brought to this organization, to this franchise, to the game of baseball, I’m sure just the money alone in September of him chasing 62 was enough to easily pay,” Yankees first baseman Anthony Rizzo said. “There’s plenty of money in this game to be spread around. For him, whatever he gets is going to be astronomical, and he deserves it.”

“Hopefully we’ll see him in pinstripes for a long time,” Yankees Manager Aaron Boone said. “I don’t even want to think about the alternative right now. But he means a lot to a lot of us in that room.”

The Yankees face many questions this off-season, starting at the top. Brian Cashman, the longest tenured general manager in M.L.B., has been in his position with the Yankees since 1998. He has a five-year deal that expires this season, and barring an unexpected change of approach by the Yankees’ managing general partner, Hal Steinbrenner, Cashman is expected to return. And despite another early playoff exit, the Yankees signed Boone to a three-year extension before the 2022 season.

But, overall, how much change is needed in order for the Yankees to finally get past the Astros, who have made six straight trips to the A.L.C.S.?

The Yankees have reached the playoffs six straight years but have been stopped in the A.L.C.S. by the Astros three times in that span, including during Houston’s since-tainted 2017 World Series-winning season.

The gap between the two franchises — despite a cheating scandal that rocked the Astros and cost their G.M. and manager their jobs and the free-agent departure of stars such as Carlos Correa, George Springer and Gerrit Cole over the years — was stark during this A.L.C.S. Including their postseason sweep of the Yankees, the Astros went 9-2 against their rival this year and outscored them, 45-31. After Sunday’s victory, Astros players partied with booze and brooms.

“Realistically, with the rest of the league, we’re still probably right up there toward the top, but they beat us in every facet,” said Cole, who signed with the Yankees before the 2020 season.

Added Yankees pitcher Jameson Taillon: “They showed up when it mattered and proved how good of a team they were. The starting pitching all the way through the bullpen, quality arms. They do a little bit of everything well in that lineup. They’ve got the power, they’ve got the lack of chase, they don’t strike out a ton. A really deep, complete team.”

The Yankees looked like one, too, in the first half of the season, when they were on a record-setting pace. But so much went wrong in the second, from health to performance. Still, they finished the regular season with 99 wins, an A.L. East title and the A.L.’s No. 2 seed in the playoffs.

Their bullpen, which was depleted by injuries, faces a lot of turnover this winter, with longtime relievers such as Aroldis Chapman, Zack Britton and Chad Green eligible for free agency. So are Taillon, a reliable starter, and Rizzo, a standout first baseman who said he had not yet decided if he would opt out of the final season of his two-year, $32 million deal with the Yankees.

So how much money — and over how many years — are the Yankees willing to commit to re-sign Judge? The Yankees, who have other holes to fill on the roster, had a $259 million payroll, the third-largest in M.L.B. this season, and have $205 million already committed next year, according to Cot’s Baseball. Could the San Francisco Giants, who have only $141 million on their ledger in 2023 and were the team Judge grew up watching in his native Northern California, come calling?

Before the playoffs began, Cashman called Judge’s gamble “the all-time best bet” and complimented how Judge has handled himself.

“There’s a pot of gold there,” Cashman said of Judge’s prize this winter. “It’s yet to be determined what the gold — how much it weighs — but it’s a pot of gold, no doubt about it. So, good for him. It was already a big pot, and obviously it’ll be bigger.”

After Sunday’s game, Judge wasn’t prepared to talk much about what was next. He said he had plenty of time later to discuss it with his family and agent. He insisted he didn’t spend any time thinking about how it could have been his final Yankees game because it ended so quickly and he was so focused on trying to win.

As he has after past playoff exits, Judge said that it was a failure any time the Yankees were not the last team standing. He said that his much-followed chase of 62 home runs did not take a toll on him going into the postseason, when he hit two home runs in the division series but went 1 for 16 in the A.L.C.S.

Boone said even great players like Judge struggled at times. Although the Yankees’ strikeout-prone offense has sputtered in past Octobers, Boone said the lineup was undermined this time by injuries to high-contact hitters such as DJ LeMahieu (foot) and Andrew Benintendi (hand). Judge said he believed the Yankees had sufficient talent to win a title.

“If I had the answer for what we were lacking, we would have addressed it by now,” he said. “As a player, all I can do is do my best every single day with the guys I’m fighting with. That’s what the front office and management and everybody else, they take care of stuff behind the scenes.”

Judge said he wasn’t sure what to expect in free agency, but he would still love to stay with the Yankees.

“I’ve been clear about that since I first wore the pinstripes,” he said. “But we couldn’t get something done before spring training, and we’ll see what happens.”

Cortes and Rizzo both said Judge, if he returned, should be named the Yankees captain, which the team hasn’t bestowed on a player since Derek Jeter, who retired in 2014. LeMahieu, who is weighing off-season surgery on his injured foot, said “we’d all be disappointed” and “shocked” if Judge were not back but that he understood the business side of the sport. Cole said his advice to Judge was to take his time with the process. Rizzo said Judge should enjoy being wooed by teams.

“He bet on himself on the biggest stage in the biggest market and did it with ease and should be rewarded as the highest paid player in the game,” Rizzo said. The highest paid position player in total contract value — $426.5 million — and average annual salary — $35.5 million — is Los Angeles Angels outfielder Mike Trout, a three-time A.L. M.V.P.

Rizzo continued, “He’s the new gold standard in my opinion, and it’s all about market timing for the most part and what better time than 62 home runs, hitting over .300 and how he’s not a Gold Glove finalist is beyond me.”

No matter what, Judge said he was proud of his time as a Yankee and called it “an incredible honor” to don the pinstripes and play right field at Yankee Stadium.

“I check myself pregame and say a little prayer, and I look around the stadium and kind of pinch myself,” he said. “There’s very few individuals that get a chance to run out on the field and do that and play in front of the fans who support us throughout my whole six years here. It was a special time. I just kick myself for not bringing home that championship.”

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