With the Yankees' season ending in the hands of the Houston Astros yet again, all eyes will focus on Aaron Judge's looming decision in free agency. After rejecting a $213 million offer before the season, Judge significantly raised his value by hitting an A.L. record 62 home runs, while knocking in 131 runs. As for the Yankees, they looked like World Series favorites going into the all-star break, but after another postseason disappointment, re-signing Judge may not be so certain. Regardless of where he signs, and for how much, Judge is already a winner of free agency.
There is still a strong possibility of him returning to the Yankees. Although he's only been on the team for six years, Judge has easily been the best player to wear pinstripes after Derek Jeter. He is a homegrown player who has represented the organization as well as anybody could for the last six years. Since Judge's rookie year, the Yankees have never missed the playoffs. Re-signing Judge would make him a Yankee for life which is a very good honor for any ballplayer. With Judge on the roster, the Yankees will certainly be playoff contenders every year. Whether he wins a World Series or not, 99 will certainly be retired someday by the organization.
However, it's worth wondering if Judge would really want to continue playing for an organization that has constantly came up short time and time again. From the team's second half slump to their playoff collapse, Judge has every right to question whether it's worth staying with a franchise that seems to be more known for their disappointment rather than their success as of late.
In this postseason, Judge might've slumped at the worst time, but he wasn't the one who couldn't convert a potential double play in an elimination game. He didn't choose to take Gerrit Cole out of the game when he was still at 95 pitches. He also wasn't the one who assembled a roster that consisted of guys who are viewed as "stopgap" players. As for the fans, Judge has every right to question whether he wants to play for a fanbase that shockingly booed him during the playoffs.
Going elsewhere would be a fresh start, and maybe even a homecoming for Judge if he signs with the hometown San Fransisco Giants who are rumored to have interest. Whereas the Yankees always seem to be stubborn in their approach towards winning, Judge may have a better chance of winning if he signs with a team that's willing to adapt year in and year out.
I think another year without a championship definitely complicates Judge's status as a Yankee. If there's anything their front office is good at, it's resigning players in free agency. However, the Yankees have thrown Judge under the bus at times, and that could haunt them this offseason. Fans should at least prepare for possibility of seeing number 99 in new threads.