In the first winter after superstar Albert Pujols shocked the baseball world by leaving the St. Louis Cardinals to sign a monster contract with the Los Angeles Angels, agents recall New York Yankees general manager Brian Cashman praising the discipline of the Cardinals’ front office, predicting — correctly — that the decision would pay off for St. Louis in the long run.
That perspective could be important now, because Cashman and his boss, Yankees owner Hal Steinbrenner, find themselves in a similar position as the Cardinals back then. The Yankees’ best and most popular player, Aaron Judge, has reached free agency, and the pressure on the Yankees to pay whatever it takes to retain Judge is enormous, just as St. Louis fans clamored for the Cardinals to pay Pujols.
For perhaps the first time in the Yankees’ storied history, the player possesses more leverage than the team. For all of their financial might, built on their enduring popularity with Yankees fans who’ve been frustrated by the team’s postseason struggles in recent years, the Yankees might need the player more than the player needs them.
The Yankees offered Judge $213.5 million over seven years in the spring, a deal that would’ve made Judge the second-highest paid outfielder in majors, behind Mike Trout — and in keeping with his habit in negotiations, Judge said no. There was no counteroffer, no further bartering. Just: No.
Judge carried that enormous risk into the season, was booed in Yankee Stadium early in the year — and then erupted, posting arguably the best season of any player since baseball began testing for steroids. He clubbed 62 homers, an American League record, and in the second half, he almost single-handedly saved the Yankees from a humiliating collapse. After the All-Star break, Judge batted .349, with a .502 on-base percentage and .785 slugging percentage, while the rest of the Yankees’ position players combined for numbers that resembled those of the Pittsburgh Pirates.
Cashman acknowledged near season’s end that Judge’s bet on himself was going to pay off, and the Yankees’ offer to Judge this offseason is higher than what was put on the table in the spring. But it’s possible that another franchise could dangle a deal that goes far beyond what the Yankees are willing to pay — and some agents don’t believe Cashman will significantly alter his recommendation to his boss.
Cashman is “emotionless in these situations,” said one agent. “They made their evaluation … about the market value [of Judge], and they’re not going to deviate much. Now, ownership could get involved, and then emotion could be brought into it.”
There are some within the Yankees organization who think Steinbrenner is willing to chase Judge in a way Cashman is not. Hal is constantly compared to his father, George Steinbrenner, whose impetuous and sometimes reckless aggressiveness drove the Yankees to championships in the 1970s, to the basement of the standings in the ’80s and, after being banned from baseball for a time, to a dynasty in the ’90s. Hal Steinbrenner was booed at Yankee Stadium last summer — as his father was, at times — and as one industry acquaintance said, “He hears that, and it’s gotta hurt.”
Steinbrenner has become personally invested in the pursuit of Judge, speaking to the outfielder repeatedly since the end of the postseason.
But historically, the Yankees’ handling of stars has been remarkably disciplined, with the front office operating with implied confidence that the franchise would thrive beyond the departures of even the biggest names. Babe Ruth was in evident decline in 1934 and released, at age 39; Ruth signed with the Braves and played part of the 1935 season. At the end of the 1951 season, the Yankees made clear their preference for the ascending Mickey Mantle, and Joe DiMaggio announced his retirement at age 37. Reggie Jackson earned the title of Mr. October with his explosive performance in the 1977 World Series, but the Yankees all but encouraged the exit of the future Hall of Famer after the 1981 season; Jackson would go on to play six more seasons with other teams. Derek Jeter’s camp sought a raise after the 2010 season for the Yankees captain, and instead Cashman — believing that Jeter didn’t possess anything close to the market value that he pursued — encouraged the shortstop to test the market; Jeter wound up taking a pay cut of about 35% at the end of difficult negotiations that impacted the relationship between the player and the team.
Robinson Cano was the game’s best second baseman in 2013, and when the Seattle Mariners offered $240 million over 10 years — far beyond where the Yankees wanted to go — Steinbrenner followed Cashman’s recommendation and did not match the Seattle offer.
Whether Steinbrenner would take the same tack for Judge remains to be seen. And for now, the Yankees must wait to see if Judge’s past rejection of their offers might actually be because he prefers to play someplace else. Judge met with the Giants for two days last week, and for the Yankees, one evaluator said, it must’ve been like seeing an estranged girlfriend on a date with somebody else: excruciating.
The Yankees drafted Judge nearly a decade ago, with staffers getting to know him as he evolved through the minor leagues, as he reached the majors. They saw his explosive emergence in the big leagues in 2017, his development as a leader, his frustration over his injuries — and his growing understanding that he could still be an effective player without a daily habit of swing repetitions. They’ve seen him deftly handle adversity, and have grown to admire him as a teammate. And yet through their contract negotiations, the Yankees aren’t entirely sure about what Judge wants into his future.
And because his preferences appear so opaque, the Yankees are considering the rest of the field, as well. Agents who have been in contact with the Yankees this offseason predict that if it becomes apparent Judge is going to sign with the Giants or some other team, Cashman and Steinbrenner will pivot quickly, just as the Braves did when their negotiations with Freddie Freeman broke down; within 48 hours of Atlanta’s last conversation with Freeman’s representation, it traded with Oakland for first baseman Matt Olson and signed the slugger to an eight-year contract. According to industry sources, the Yankees have spoken internally about alternatives, in the event Judge departs. “[Cashman] wouldn’t be doing his job if they weren’t prepared for that possibility,” one agent said.
The best of the rising prospects in the Yankees’ organization are shortstops, Anthony Volpe and Oswald Peraza, but if Judge leaves, the Yankees would more seriously explore the group of veteran shortstops that is the best of the current free agent class — Trea Turner, Xander Bogaerts, Carlos Correa and Dansby Swanson. Bogaerts and Turner could be the best fits for New York, because of the flexibility each would immediately provide if Volpe or Peraza graduate into full-time shortstops at the big-league level.
Bogaerts, 30, could play shortstop for the Yankees in 2023, and as Volpe and/or Peraza ascend, he could move to third or second in subsequent seasons. Bogaerts would add more contact and balance to the Yankees’ lineup — he has batted .304 over the past four seasons, with 215 extra-base hits — and he likely will come at a price lower than Turner or Correa. And any concern about Bogaerts’ transition to the intense market of New York would be mitigated, given his vast experience playing in Boston.
Turner, 29, is an extraordinary athlete who has already demonstrated positional flexibility in the big leagues, playing center field and second base; there is little doubt among evaluators that as he ages, he could easily move to another position. And he is a dynamic offensive player: He had 304 total bases for the Los Angeles Dodgers last season, with 194 hits (64 extra-base hits), 101 runs scored and 100 RBIs. He is an elite base-stealer, with 230 steals in 272 attempts in his career, the sort of skill that could be even more coveted as MLB limits pick-off throws next season.
The Yankees could also pursue free agent outfielder Andrew Benintendi and a starting pitcher, while looking to fortify a bullpen that was decimated by injuries at the end of last season. Regardless of whether Judge is in Yankees pinstripes next season, the organization will continue to push for its first championship since 2009; there is no talk of a major reset, no talk of rebuilding. Gerrit Cole, who owns the most expensive contract on the team, is 32 and a frontline starting pitcher, with Nestor Cortes, Luis Severino and good bullpen pieces behind him.
The strong organization preference is to retain Judge, but some experienced agents expect Cashman will embrace the challenge of building the team without its core superstar. If the Giants or some other team is inspired by Judge’s record-setting season, ability and stardom and lays down a whopper offer, Cashman and Steinbrenner will face a tough decision. Whichever way they land, the choice will say a lot about the Yankees and their direction.