Will Aaron Judge leave the Yankees as a free agent?


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

In 2017, he won the American League Rookie of the Year Award and was 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 was an All-Star four times, including this season when he hit an AL record with 62 homers and carried the Yankees through their many ups and downs.

So it was only fitting that Judge came up for batting in the ninth inning in Game 4 of Sunday’s best-of-seven AL 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 on an outfield and produced a weak groundball that Astros closer Ryan Pressly turned to first baseman Yuli Gurriel for the finale. As the Astros began celebrating their fourth trip to the World Series in six years, Judge headed to the Yankee Stadium dugout for what might be his final time.

“Anybody celebrating on this field isn’t fun to watch,” he said late Sunday night while standing in a Yankees celebratory clubhouse.

Now the baseball world will watch as Judge’s future is decided. Five days after the World Series ended, the 30-year-old judge was allowed to speak with one of MLB’s 30 teams for the first time in his career as a free agent. The future of the Yankees — a franchise that loves to celebrate its winning tradition but hasn’t competed in or won a World Series since 2009 — is intertwined with that of Judge.

“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 a long time. He carries a lot of weight here. He’s a superstar.”

“The money that he brought to this organization, this franchise, the baseball game, I’m sure the money alone in September when he was pursuing 62 was enough to easily pay for it,” said Anthony Rizzo, first baseman of the Yanks. “There is a lot of money in this game that can be distributed. For him, whatever he gets will be astronomical and he deserves it.”

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

The Yankees face many questions this offseason, starting at the helm. Brian Cashman, the longest-serving general manager in MLB, has been in his position with the Yankees since 1998. He has a five-year contract that expires this season and barring an unexpected change in approach from the Yankees’ managing general partner Hal Steinbrenner, Cashman is expected to return. And despite another early exit from the playoffs, the Yankees extended Boone by three years ahead of the 2022 season.

But overall, how much change will it take for the Yankees to finally get past the Astros, who have made six straight trips to the ALCS?

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

The rift between the two franchises — despite a cheating scandal that rocked the Astros and cost their GM and manager their jobs, and free agent departures over the years of stars like Carlos Correa, George Springer and Gerrit Cole — was during this ALCS big Including their postseason win over the Yankees, the Astros went 9-2 this year against their rival and surpassed them 45-31. Astros players celebrated with booze and brooms after Sunday’s win.

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

Yankees pitcher Jameson Taillon added, “They showed up when it mattered and proved how good they are as a team. The initial pitching to the bullpen, quality weapons. They do a little bit of everything well in this lineup. They have the power, they have the lack of pursuit, they don’t turn down much. A really deep, complete team.”

The Yankees also looked the part in the first half of the season when they had a record-breaking pace. But in the second so much went wrong, from health to performance. Despite this, they finished the regular season with 99 wins, an AL East title and the AL’s No. 2 spot in the playoffs.

Their bullpen, exhausted by injuries, faces a ton of turnover this winter, with long-time helpers like Aroldis Chapman, Zack Britton and Chad Green all available for free play. So is Taillon, a dependable starter, and Rizzo, a standout first baseman who said he hasn’t yet decided whether to step out of the final season of his two-year, $32 million contract with the Yankees.

But of course, the Yankees’ tallest free agent — and the tallest in the entire sport — is Judge, and not just because of his 6-foot-7 frame.

During spring training, Judge turned down a contract extension that would have guaranteed him $213.5 million over seven years. He also declined to negotiate during the season. That bet paid off: After multiple injuries in previous seasons, Judge played in 157 of the Yankees’ 162 regular-season games, rewrote the record books, played strong defense, and was a team captain. Meanwhile, he’s been instrumental in growing the viewership of the YES Network, part-owned by the Yankees.

So how much money — and over how many years — are the Yankees willing to commit to Judge’s re-signing? The Yankees, who have other gaps to fill on the roster, had a $259 million payroll, the third-biggest this season in MLB, according to Cot’s Baseball, and have already committed $205 million next year. Could the San Francisco Giants, who have just $141 million in their tally in 2023 and grew up team judges in his native Northern California, calling?

Before the playoffs began, Cashman called Judge’s Gamble “the best bet ever” and praised how Judge handled himself.

“There’s a pot of gold there,” Cashman said of the judge’s award this winter. “It has yet to be determined what the gold is – how much it weighs – but it is undoubtedly a pot of gold. So good for him. It was already a big pot and obviously it’s getting bigger.”

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

As he has done after past playoff exits, Judge said that whenever the Yankees weren’t the last team standing, it was a failure. He said his much-publicized 62-homer chase didn’t weigh him down ahead of the postseason, when he hit two homers in the Division Series but won 1-to-16 in the ALCS

Boone said even big players like Judge struggled at times. Though the Yankees’ strikeout-prone offense faltered last October, Boone said the lineup this time around was eroded by injuries to high-contact hitters like DJ LeMahieu (foot) and Andrew Benintendi (hand). The judge said he believed the Yankees had enough talent to win a title.

“If I knew the answer to what we were missing, we would have addressed it by now,” he said. “As a player, I can only do my best every day with the guys I fight with. That’s what the front office and management and everyone else do, they take care of the behind-the-scenes things.”

The judge said he wasn’t sure what to expect in a free hand, but he’d still like to stay with the Yankees.

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

Cortes and Rizzo both said that if Judge returns, he should be named Yankees captain, something the team hasn’t bestowed on a player since Derek Jeter, who retired in 2014. LeMahieu, who is considering off-season surgery on his injured foot, said “we would all be disappointed” and “shocked” if Judge wasn’t back, but that he understood the business side of the sport. Cole said his advice to the judge is to take your time with the trial. Rizzo said Judge should enjoy being courted by teams.

“He bet on himself on the biggest stage of 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 positional player in terms of total contract value — $426.5 million — and average annual salary — $35.5 million — is Los Angeles Angels outfielder Mike Trout, a three-time ALMVP

Rizzo continued, “He’s the new gold standard in my opinion and it’s mostly about market timing and what better way than 62 homers to hit over .300 and that he’s not a Gold Glove finalist is beyond me.”

Anyway, Judge said he was proud of his time as a Yankee, calling it “an incredible honor” to don the pinstripes and play on the right field at Yankee Stadium.

“I check myself before the game and I say a little prayer and I look around the stadium and I kind of pinch myself,” he said. “There are very few people who get the chance to run onto the field and do that and play in front of the fans that have supported us throughout my six years here. It was a special time. I’m just kicking myself for not bringing that championship home.