If I Were Hal Steinbrenner: The Offseason To-Do List The Yankees Cannot Duck

In my view, the picture is pretty clear. The Yankees went 94-68 in 2025, finished second in the AL East by tiebreaker, beat Boston in the Wild Card Series, and then lost the ALDS 3-1 to Toronto.

They were not some smoke and mirrors club. This team led the majors with 849 runs scored and 274 home runs, and finished with a plus 164 run differential. Aaron Judge put up another MVP season in the middle of it all.

At the same time, they are now fifteen years removed from their last parade and coming off another October where a division rival sent them home. Hal Steinbrenner has already said publicly that they are looking at “every area of need,” talking specifically about another outfielder and a better bullpen.

So if I traded places with Hal for one offseason, what would I actually do? Here is my to-do list, in order.

1. The Big Picture: Decide What The Yankees Want To Be

If I were Hal, the first thing I would do is get brutally clear on the vision.

In my view, the Yankees have been stuck in the middle on philosophy. They want to act like a big market bully in free agency, but they also talk about wanting a lower payroll after running around 319 million dollars in 2025. They say the standard is championships, but the moves have not always matched that urgency.

My version of the job would start with a simple statement that everyone in the building hears:

The Yankees exist to win the World Series in the next three to five years while Aaron Judge and Max Fried are still at their peak.
We will still care about the long term, but we are not going to pretend 2031 matters as much as 2026 right now.
If there is a move that clearly makes the 2026 and 2027 Yankees better, we are open to doing it, even if it stings later.

That sounds obvious, but you can see in the way some recent offseasons have gone that the team has tried to walk a line between “all in” and “responsible.” I think this core is too good, and this division is too tough, to keep playing that half step.

2. Fixing The Front Office And Philosophy

Once the big picture is set, my first concrete item would be on the leadership side.

Keep The Structure, Add Real New Voices

If I were Hal, I would not blow up the entire front office. Brian Cashman and his group helped put together a 94 win, league leading offense around Judge, and they landed Max Fried when they needed a co ace. That matters.

However, I would add two things:

A high level outside voice with real authority on run prevention – someone who lives and breathes defense, pitching development, and how to build an October style staff.
A small, empowered group whose job is to challenge the assumptions of the existing analytics department, not just nod along.

Too often the Yankees have looked like a team that knows how to win 94 games on paper, but not always how to win Game 4 when the bullpen is tired and the opponent refuses to chase. I think that is philosophy as much as personnel.

Boone And The Field Staff

On the field, I would bring Aaron Boone back, but I would make the expectations very clear.

In my view, Boone’s biggest strengths are communication and keeping the room from turning on itself in bad stretches. This team has had some brutal slumps and never completely cratered in the standings, and that is not nothing in New York.

Where I want more is in October feel. If I were Hal, I would:

Add a veteran bench coach with a track record of aggressive in game strategy.
Push for more matchup creativity in the postseason, even if it means breaking regular season roles.

I would not fire Boone just to send a message. I would, however, make sure he has the staff around him to manage a modern postseason series the way the very best dugouts do.

3. Rebuilding The Roster: Offense

Now we get to the part everyone loves: players.

The funny thing about the 2025 Yankees is that the offense really did what it was supposed to do overall. They finished first in runs and home runs, and Judge put up another absurd line in the middle of it. Jazz Chisholm Jr. hit a career high 31 homers in his first full year in pinstripes, and Cody Bellinger gave the lineup balance and versatility.

If I were Hal, my priorities on the position player side would look like this.

3A. Keep The Power, Add More Ways To Score

I would tell the front office very clearly:
We are not running from our identity as a power team. We are adding to it.

The moves would be:

Re sign or replace Bellinger with a player who brings three things: left handed thump, above average defense in a premium spot, and the ability to hit good pitching.
Add at least one everyday bat whose main value is on base skills and bat control, not just slug. Someone who shortens up with two strikes, puts the ball in play, and grinds at bats even when the ball is not flying.
Improve the bottom third of the lineup so that it is not a black hole against right handed pitching.

When a team leads the league in homers, opponents will game plan to take the long ball away in October. I think the Yankees need two more players who are comfortable winning 3 2 on singles and doubles, not just towering shots into the night.

3B. Clean Up The Defense

On defense, the Yankees have gotten more athletic, but I still would not call run prevention a strength.

If I were Hal, I would make it clear that any marginal offensive upgrade is not worth a big defensive downgrade anymore. That means:

Prioritizing plus gloves in center field and at least one infield spot even if their OPS starts with a 7 instead of an 8.
Working with players like Jasson Dominguez to either get their reads and routes up to standard or move them to positions where they can succeed.
Making sure the catching tandem can handle both the running game and the game planning demands of a modern staff.

The 2025 ALDS reminded all of us how thin the margins are when you are trying to hold down a lineup like Toronto. One extra out or one extra base can flip an entire series.

4. Rebuilding The Roster: Pitching

If I could only fix one area this winter as Hal, it would be the pitching staff.

4A. Rotation – From “Good” To “Overwhelming”

The top of the rotation is in good shape. Fried looked like a true ace, Rodón missed bats the way the Yankees hoped when they signed him, and Cole should return at some point in 2026 if his rehab stays on schedule.

The problem is everything that happens when one of those arms is not on the mound.

If I were Hal, I would push for:

One more playoff caliber starter – not just a back end innings eater, but someone who can realistically start Game 2 or 3 in a postseason series.
A stronger fifth and sixth starter group, so that injuries and off days do not turn into automatic four hour bullpen marathons.

This does not all have to be done through giant free agent contracts, but I would not be shy about going to the top shelf if the right arm is out there. The Blue Jays just showed the entire division what an aggressive rotation build looks like. The Yankees cannot answer that with only depth signings.

4B. Bullpen – Build A Trust Tree, Not Just A Top Three

The bullpen is where I think the Yankees have been faking it the most in October.

Every year it feels like the same story. There are two or three relievers Boone truly trusts, then a steep drop off. In a five game series against a powerful lineup, that is not enough.

If I were Hal, my instructions would be simple:

Give the manager seven relievers he is comfortable using in a tie game in the sixth inning, not three.
Prioritize strikeout stuff and durability. The playoffs are not the place for “pitch to contact and hope.”
Add at least one multi inning weapon who can bridge from a short start to the back end without exposing the middle.

Some of that can come from within, some of it will have to come from outside. What matters is that the bullpen reflects the intensity of October, not just the grind of June.

5. Trusting The Kids: Prospects And The Youth Movement

One of the trickiest parts of this job would be balancing the present with the future. The Yankees have already seen what happens when they fall in love with the idea of prospects instead of the reality.

If I were Hal, I would separate the young core into two buckets.

Players who are part of the next great Yankees team:
- Anthony Volpe, who still has a chance to be an above average shortstop if the offense catches up to the glove.
- Cam Schlittler, who already showed in the Wild Card Series that he is not afraid of the stage.
- A small group of high ceiling arms and position players that player development really believes in.
Players who are more valuable as trade chips:
- Prospects blocked by multiple established players at their position.
- Players whose perceived value around the league is higher than what the Yankees see internally.

The rule I would live by is simple. If a prospect can realistically be an impact contributor on a World Series team in the next three years, I am reluctant to move him. If not, he is on the table in the right deal.

What I would not do is hug every young player until the roster calcifies. That is how you end up watching other teams hoist a trophy while your highest upside talent is still “developing” in Triple A at age 25.

6. Raising The Standard Again

The last part of my to-do list is not about a specific signing or promotion. It is about how this organization talks about itself.

If I were Hal, I would retire a few phrases for a while:

“We ran into a hot team.”
“The playoffs are a crapshoot.”
“We had a great regular season.”

There is truth in all of those lines, but they also become crutches. At some point, a franchise like the Yankees has to put the focus back on its own standard.

Internally, I would push for:

Harder conversations after October exits, not just “we were close” speeches.
Clearer public expectations, especially around players being in shape, playing clean defense, and executing situationally.
A little more edge from the top. That does not mean becoming a caricature of George, but it does mean making it clear that another 94 win, early exit season is not acceptable as the new normal.

The talent is here. The money is here. The question is whether the urgency will match the opportunity.

The Bottom Line: My Hal Steinbrenner Checklist

If I had Hal’s job for a winter, my list would look like this:

Commit fully to the Judge and Fried window and accept that now is the time to be aggressive.
Add real outside voices to the front office and coaching staff, especially around pitching and run prevention.
Keep the core of this offense together, but add more contact and another high end defender so the lineup has more ways to score.
Push the pitching staff from “good enough to get there” to “scary once we arrive,” with one more top starter and a deeper, more dynamic bullpen.
Be honest about which prospects are future stars in pinstripes and which are better used to bring in the missing pieces.
Reset the organizational tone so that 94 wins and an ALDS loss is viewed as a failure, not a sign that the process is working.

If the Yankees do not seriously address these issues, I think we are headed for more of the same. More October cameos. More stories about how much they spent without a parade at the end of it.