The Crusaders enter 2026 as back-to-back Section IX Class AA champions. Key contributors are gone, new players will have to emerge, but the expectation inside Monroe-Woodbury has not changed.
Monroe-Woodbury is not entering the 2026 football season talking like a program preparing to rebuild.
The Crusaders are talking about defending.
That distinction matters.
Monroe-Woodbury is coming off a 10-2 season, an undefeated run through Section IX Class AA play and a second consecutive Section IX Class AA championship. The Crusaders beat Valley Central 42-13 in the sectional semifinal before surviving Middletown 28-21 for the title.
For some programs, back-to-back sectional championships would represent the destination.
Inside Monroe-Woodbury, the players discussing 2026 sounded more interested in making sure the run continues.
Returning seniors Braylon Shillingford, Elijah Sosa, Tyler St. Jean and quarterback Ethan Maldonado made that clear during their conversation with KOT845 Media.
“We look to do the same thing every single year,” Shillingford said. “Get to those playoffs every year. Win the championship.”
For Monroe-Woodbury, the success of the last two seasons has reinforced an expectation that goes beyond one graduating class.
Winning Section IX is not being presented as something the Crusaders hope to do if everything goes right.
It is what they believe Monroe-Woodbury football is supposed to do.
“I feel like that’s our standard,” Maldonado said. “Always making the state playoffs, winning the Section championship and just fighting for the state championship.”
Back-to-Back Titles, But Still Something Left
The Crusaders have plenty to be proud of from 2025.
They went 6-0 in league play.
They entered the postseason at 9-1.
They handled Valley Central in the semifinal.
Then came Middletown.
The Middies had already pulled off one of the postseason’s biggest results, beating Newburgh Free Academy 21-16 to earn their spot in the Class AA championship game. It set up a Monroe-Woodbury versus Middletown sectional final for the second consecutive season.
And this one was anything but easy.
Monroe-Woodbury had beaten Middletown 49-13 during the regular season, but the championship rematch became a completely different game. The Middies erased a two-touchdown deficit and tied the game at 21 in the fourth quarter before Monroe-Woodbury found the answer late.
Maldonado connected with Shillingford for the go-ahead touchdown with less than two minutes remaining, and the Crusaders held on for a 28-21 victory. Maldonado finished the championship game with 226 passing yards and three touchdown passes, while Shillingford caught five passes for 89 yards.
Another Section IX championship belonged to Monroe-Woodbury.
But the season still did not feel finished.
One week later, the Crusaders met Section I champion Mamaroneck in the state quarterfinal at Arlington High School.
Monroe-Woodbury’s season ended by the smallest possible margin.
Mamaroneck won 25-24.
“We were so close,” Maldonado said. “But, you know, football happens. I feel like it was a little short run, but we’ll be right back.”
That ending gives the 2026 Crusaders something different to carry with them.
They know what winning a section feels like.
They also know how quickly a state championship opportunity can disappear.
For a team that has now won consecutive Section IX titles, that next step becomes impossible to ignore.
St. Jean pointed to injuries and the physical toll of the end of the season as part of what made the finish difficult.
But when the conversation shifted back toward expectations, his answer was simple.
“Winning championships is the standard,” St. Jean said. “That’s what we like. That’s what we do. Just win.”
The Production Coming Back Matters
Monroe-Woodbury will lose important pieces from last year’s championship team.
But this is not a roster starting completely over.
Maldonado returns after establishing himself as one of the major offensive pieces of the Crusaders’ 2025 run. He threw for 1,316 yards and 21 touchdowns while adding 11 rushing touchdowns.
Shillingford also returns after leading Monroe-Woodbury with 683 receiving yards and six receiving touchdowns last season.
Those numbers matter.
So does the experience behind them.
Maldonado and Shillingford were not watching Monroe-Woodbury’s championship run from the sideline. They were producing in its biggest games.
St. Jean gained important varsity experience on the line, including seven recorded quarterback hurries last season. Sosa gives the Crusaders another senior presence up front as Monroe-Woodbury works to replace graduated players around its returning core.
Still, repeating will require more than the players everybody already knows.
That is where the conversation inside the program appears to be shifting.
Replacing Players Without Replacing the Standard
The question for Monroe-Woodbury is not whether talent graduated.
It did.
The question is whether the next group is ready to accept what comes with replacing it.
Shillingford believes some of the younger Crusaders already understand the opportunity in front of them.
“We already have guys that are hungry for a Section title to their name,” Shillingford said. “They’re pushing harder than most of us that are returning.”
That may be one of the most important statements to come out of Monroe-Woodbury’s preseason.
Championship programs eventually reach a point where winning cannot belong only to the players who have already done it.
The standard has to transfer.
Sosa described that process through what he called a “big brother, little brother” relationship inside the program.
Older players teach younger ones.
Players who have already experienced varsity football help prepare the ones who have not.
Eventually, those younger players become responsible for carrying it forward themselves.
For a Monroe-Woodbury team attempting to win a third consecutive sectional championship, that cycle becomes critical.
The graduated seniors cannot help the Crusaders win in 2026.
Someone else has to take their snaps.
Someone else has to make their tackles.
Someone else has to become the player Monroe-Woodbury trusts when a championship game is tied late in the fourth quarter.
St. Jean said the coaching staff continuously puts that responsibility in front of the team.
“Coach always tells us, ‘Who’s going to be the one to step up?’” St. Jean said. “That’s what we really emphasize in Monroe.”
Maldonado sees some of those answers beginning to emerge.
“We lost a lot of people last year, but we’re definitely developing and bringing up new kids that definitely could fill those spots for us,” Maldonado said. “They’re doing what they’re doing at practice.”
That is the challenge.
Monroe-Woodbury does not need the 2026 team to become an exact copy of the 2025 team.
It needs the next group to become championship capable in its own way.
Middletown and NFA Still Carry Extra Weight
Monroe-Woodbury’s championship goals extend well beyond one regular-season opponent, but there was no hesitation when the players were asked about the games that carry a little something extra.
Newburgh was one.
“We’re always looking forward to our Newburgh rivalry,” Shillingford said. “I feel like that’s our biggest game, but we always look forward to the championship no matter what.”
The history between the two programs makes that understandable.
Monroe-Woodbury beat NFA 49-15 last October as part of its unbeaten Class AA run, but rivalry games rarely need much additional explanation.
Then there is Middletown.
At this point, that matchup has championship history attached to it.
The Crusaders and Middies have met in each of the last two Section IX Class AA championship games, with Monroe-Woodbury winning both.
Sosa pointed to Middletown and Newburgh as the two games he personally looks forward to most.
Maldonado did the same while making sure to establish the order in which Monroe-Woodbury believes those games have to be approached.
“Obviously we take it one game at a time,” Maldonado said. “Focus on the next game. But our biggest opponents are definitely Middletown and NFA.”
Both games will come on the road in 2026.
Monroe-Woodbury is scheduled to visit NFA on October 2 and Middletown on October 23 as part of a Class AA league schedule that also includes Kingston, Valley Central and Pine Bush.
Those games will help determine positioning.
They will create rivalry-week attention.
They may eventually shape the sectional playoff bracket.
But Monroe-Woodbury’s players have made it clear that beating Middletown or NFA by itself would not define a successful season.
Their target sits beyond any one Friday night.
The Next Step
That is what makes Monroe-Woodbury’s 2026 season worth watching.
This is no longer simply a team trying to prove it can win Section IX.
The Crusaders have already done that.
Twice in a row.
The more interesting question now is what comes next.
Last year’s 25-24 loss to Mamaroneck showed exactly how thin the margin becomes once Section IX’s champion reaches the state tournament. Monroe-Woodbury was one point from advancing.
The returning Crusaders remember that.
They also remember celebrating another sectional championship.
Now both experiences become part of the responsibility placed on the 2026 team.
Maldonado has to lead another offense.
Shillingford has to continue producing while taking on an even larger leadership role.
Sosa and St. Jean have to help set the tone up front.
And around them, Monroe-Woodbury needs another wave of players to become ready before November arrives.
That is how standards survive graduation.
Not because the same players return forever.
Because the next group accepts what is expected.
Monroe-Woodbury has new faces to develop.
New leaders to find.
And another difficult Class AA road ahead.
The expectation, though, sounds exactly the same.
Win Section IX. Get back into the state tournament. And see how far this version of Monroe-Woodbury can take it.
New faces.
New leaders.
Same standard.
KOT845 Media will continue its 2026 Section IX football coverage throughout the preseason and regular season at KOT845.com and @kot845.media.
