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.