About the Off-Season: If.

About the Off-Season: If

By Tim Kabel

December 31, 2025

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There is a famous poem, ' If ' by Rudyard Kipling which I truly enjoy reading. If you have never read it, I recommend that you do so. There is one line in the poem that I would like to quote for today's article.

“If you can dream - and not make dreams your master.”

I would like to apply that thought to the 2026 New York Yankees. However, before we do that, we need to acknowledge that there are a lot of Ifs associated with the Yankees regarding the 2026 season. The first If is probably the most important. 

If the Yankees are not going to make any more additions to the team, then this will be the hand we are dealt as fans. We will have to accept the roster for what it is and address all those attached concerns. Having established that as our premise, let's break the team down assuming the goal is for the Yankees to win the World Series. After each item is considered, I will offer my assessment of its probability of being achieved on a scale of 1 to 10, with one being not at all likely and 10 being the most likely thing in the world.

If the Yankees are going to win the World Series in 2026- Austin Wells will have to improve his offensive production drastically and remain healthy all season. 5/10

If the Yankees are going to win the World Series in 2026- Ben Rice will need to continue his development and prove that he is capable of being a full-time Major League first baseman and a major offensive threat. 8/10

If the Yankees are going to win the World Series in 2026- Jazz Chisholm, Jr. will need to remain injury free and at the very least, replicate his 2025 numbers in his walk year. 8.5/10

If the Yankees are going to win the World Series in 2026- Anthony Volpe needs to be fully recovered from his surgery and to improve drastically on both his offensive and defensive numbers from 2025. He needs to take a major step forward after leading the league in errors and putting up inconsistent and extremely streaky offensive numbers in 2025. 2.5/10

If the Yankees are going to win the World Series in 2026- Ryan McMahon must provide much more than exceptional defense. He has to prove that he is not an offensive liability and produce offensively on a consistent level. 3/10

If the Yankees are going to win the World Series in 2026- Jasson Dominguez must be given a full and legitimate opportunity to play regularly and to realize his potential. Then, he must prove that he deserves to be the everyday leftfielder. 4/10 for the first part; 8/10 for the second part.

If the Yankees are going to win the World Series in 2026-   Trent Grisham has to show that the numbers he put up in the 2025 regular season were not an aberration and that he has finally realized his potential. 3/10

If the Yankees are going to win the World Series in 2026- Spencer Jones must be given a legitimate chance to win the starting centerfield job in Spring Training. If he does not and Trent Grisham struggles during the season, Jones must be allowed the opportunity to seize the position. 3/10

If the Yankees are going to win the World Series in 2026- Aaron Judge has to perform at his usual MVP level. 10/10

If the Yankees are going to win the World Series in 2026- Giancarlo Stanton has to remain injury free, play a full season, and produce at a similar level to that which he did in 2025. 2/10

If the Yankees are going to win the World Series in 2026- The starting rotation needs to be relatively injury free and be a major strength for this team. Gerrit Cole and Carlos Rodon need to make timely returns from the IL and to pitch effectively. Luis Gil needs to avoid injury and improve his control. Cam Schlittler and Will Warren need to continue to mature and develop and to become reliable and consistent members of the rotation. Max Fried needs to replicate his 2025 season. 6/10

If the Yankees are going to win the World Series in 2026- The bullpen needs to be much more effective and consistent than it was in 2025. It needs to be more of a strength and less of a liability than it was last season. 4/10

If the Yankees are going to win the World Series in 2026- Aaron Boone needs to become a consistent and effective Major League manager in his ninth season in that role. He needs to develop and trust his young players to help them reach their full potential. He needs to avoid yet another Boone-Swoon.  1/10

If the Yankees are going to win the World Series in 2026- Hal Steinbrenner and Brian Cashman need to show a commitment to improving the team in any way possible with a focus on building a championship team as opposed to adhering to self-imposed budgetary constraints. 1/10

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I realize I have painted a rather bleak picture here. I truly want the Yankees to win the World Series in 2026. But wanting something doesn't always mean that it will happen. If the Yankees are unwilling to bring in better players and want to proceed with the status quo, then that is the reality we must face. As I stated at the outset of this article, I was adhering to the following premise.

“If you can dream - and not make dreams your master.”

Unfortunately, reality can be a rigid and unyielding taskmaster. For the Yankees to win the World Series in 2026, a whole lot of those Ifs listed above need to happen. That's asking a lot. Of course, anything is possible, but possible and likely are not the same thing. 

If only they were.