Two years ago, Monroe-Woodbury was trying to return to the top of Class AA.
Now everyone else is trying to knock the Crusaders down.
Monroe-Woodbury enters the 2026 season as the two-time defending Section IX Class AA champion. The Crusaders defeated Middletown in the championship game in both 2024 and 2025, finishing last season with a 10–2 overall record.
The program has already completed the comeback.
Now it is chasing history.
From Challenger to Champion
Before its current run, Monroe-Woodbury had not won a sectional championship since 2016.
Newburgh controlled Class AA from 2016 through 2022, winning five consecutive sectional championships during seasons in which a title game was played. Middletown then broke through in 2023.
The classification’s balance shifted again in 2024.
Monroe-Woodbury defeated Middletown 34–10 in the Class AA championship game, capturing its first sectional title in eight years. The victory restored one of Section IX’s most recognizable programs to the top of its classification.
But winning once and staying there are two different challenges.
The Crusaders entered 2025 with every contender preparing to take the championship back. They responded by going undefeated in league play and returning to the final.
Once again, Middletown stood across from them.
This time, the battle was much closer.
Monroe-Woodbury earned a 28–21 victory and secured its second consecutive Class AA championship. Quarterback Ethan Maldonado threw three touchdown passes, helping the Crusaders survive their greatest sectional test of the season.
A return had officially become a run.
The Pressure of a Three-Peat
Winning consecutive championships changes the expectations surrounding a program.
Monroe-Woodbury will not enter 2026 as a team hoping to contend. Anything short of another championship will feel like the end of an opportunity.
That is the pressure attached to chasing three.
The Crusaders are attempting to become the first Class AA program since Newburgh’s dominant run to win at least three consecutive Section IX championships.
They will also receive every opponent’s best effort.
For Newburgh, Middletown and the rest of Class AA, beating Monroe-Woodbury would mean more than winning another regular-season game. It would provide evidence that the classification is ready to change hands.
Monroe-Woodbury must prepare for an entire season in which it represents the standard.
Ethan Maldonado’s Final Run
The three-peat attempt will place significant responsibility on Ethan Maldonado.
Maldonado enters his senior season as one of Section IX’s most accomplished active quarterbacks. He has led the Crusaders through consecutive championship seasons and delivered three touchdown passes in the 2025 title game.
He has already proven that he can win Class AA.
The remaining challenge is finishing the run.
A third consecutive championship would give Maldonado a unique place in Monroe-Woodbury’s history. It would also strengthen the Crusaders’ argument as Section IX’s defining Class AA program of this period.
However, another sectional championship will not be the only goal.
Monroe-Woodbury finished 10–2 last season but fell one point short against Mamaroneck in the state quarterfinal. That result left the Crusaders just short of extending their season and competing for something beyond Section IX.
The next step is clear: defend the classification and advance deeper into the state tournament.
The Challengers Are Waiting
Monroe-Woodbury may be the champion, but Class AA will not simply concede another title.
Middletown has reached the championship game in three consecutive seasons. The Middies defeated Newburgh in last year’s semifinal before pushing Monroe-Woodbury throughout the final.
Newburgh remains one of Section IX’s most talented programs. The Goldbacks finished 6–4 in 2025 and reached the sectional semifinals, but their standard is measured by championships—not playoff appearances.
Valley Central reached the postseason for the first time in a decade last season and now begins a new era under head coach Kyle Schneider.
Pine Bush and Kingston enter the year needing to close the gap, but both have an opportunity to reshape the playoff race.
Every contender has a different reason to believe 2026 can be its year.
All of them must go through Monroe-Woodbury.
More Than One Quarterback
Maldonado will receive much of the attention, but a third championship cannot be won by one player.
The Crusaders must replace graduated contributors, rebuild parts of their supporting cast and continue developing the depth that carried them through the previous two seasons.
Protection will matter. The running game will matter. Defense and special teams will matter.
Championship programs survive graduation because their systems continue producing players prepared to step into larger roles. Monroe-Woodbury’s greatest test may be whether its overall program remains strong enough to support its experienced quarterback.
The Crusaders are no longer proving that they can return to the top.
They are proving that they can remain there while the roster around their established leaders changes.
Can Anyone Stop the Standard?
Monroe-Woodbury’s position entering 2026 is simple.
The Crusaders have the championships. Everyone else has the opportunity to take them away.
Middletown has come close. Newburgh possesses the talent. Valley Central is attempting to rise. The rest of the classification wants to change the conversation.
But until someone defeats Monroe-Woodbury when the championship is at stake, Class AA still belongs to the Crusaders.
One title marked their return.
Two established their control.
A third would define the run.
