Because it is the region where the defending ‘AAA’ and State Champion is, I thought it would be appropriate to start in Westchester County. Westchester draws most of their students from Fairfield County in CT, the Bronx, and Rockland and Putnam counties, which has a total population of 2.75 million people.

The CHSFL schools in Westchester are:

• Kennedy Catholic College Preparatory School
• Archbishop Stepinac High School
• Iona Preparatory School

Kennedy Catholic

Kennedy is in Somers, NY, quite a far bit north. They joined the CHSFL for the 2013 season, jumping from Section 1. Their best season so far has been the 2019 season, where they won a ‘AA-2’ championship crown. In 2018, the Gaels from Somers went undefeated in the ‘A’ division, before losing to Cardinal Spellman in the championship game. Being one of the three members of the CHSFL in Westchester, Kennedy has to compete with the likes of Iona Prep and Stepinac for athletes in football, a tall task for a small co-ed school, with only around 600 students from grades 9-12. 

Post Covid, here is their record:

• 2021: 5-5, loss in the ‘AA-2’ Semifinals to St. John the Baptist
• 2022: 3-7, loss in the ‘AA-2’ Semifinals to Xavier High School
• 2023: 3-8, loss in the ‘AA-2’ Semifinals to Mount Saint Michael
• 2024: 2-7, loss in the ‘AA-2’ Semifinals to Holy Cross
• 13-27 overall from 2021-2024

Four tough seasons in a row for Kennedy, but with the expansion of the ‘AA-2’ (the additions of St. Dominic’s and Nazareth), I think the Gaels can win more games this year. The main issue is I don’t see them returning much of anything on their roster. Their best players are gone. 

Their 2025 League Schedule is below:

Saturday, September 13, 2025	Holy Cross
Saturday, September 20, 2025	@ St. Dominic’s
Saturday, September 27, 2025	@ Nazareth
Saturday, October 4, 2025	Christ the King
Saturday, October 11, 2025	BYE
Saturday, October 18, 2025	@ St. Francis Prep
Saturday, October 25, 2025	Xaverian
Saturday, November 1, 2025	Cardinal Spellman

Kennedy was able to beat Cardinal Spellman last season, and they play two full time newcomers in St. Dominic’s and Nazareth. I can see them winning 3 games this year, if they manage to beat Christ the King, but I just don’t know. A lot of their best players have left, and it is hard to gauge what remains, as it is a smaller program. 

Archbishop Stepinac

In White Plains, the recent four time ‘AAA’ Championship winning program had a tough year, and has not been to a championship game since winning it in 2018. The Crusaders just had one of their toughest years yet, winning only one game. With the retirement of their coach, Mike O’Donnell (who won 238 games in 37 years at Stepinac, including four ‘AAA’ Championships, and three ‘AA-1’ Championships), this will represent the 2nd time the program has had to reset in the last five years. Once after Covid, and now, with new Coach AJ Magee. Coach Magee takes over a program that is loaded, and one that has a recent tradition of winning at the highest level. Due to them having three levels, the football program is healthy, and with an enrollment of 785 boys, the Crusaders should be able to compete for years to come. 

Post Covid, here is their record:

• 2021: 7-4, loss in ‘AAA’ semifinals to Monsignor Farrell
• 2022: 8-3, loss in ‘AAA’ semifinals to Iona Prep
• 2023: 8-3, loss in ‘AAA’ semifinals to Cardinal Hayes
• 2024: 1-10, loss in ‘AAA’ first round to St. Anthony’s
• 24-20 from 2021-2024

While they lost their Senior QB, Mason Hoover, RB Troy Baker, and their Senior WR, Zaire Spellman, the rest of the Crusaders’ contributors were Juniors. The lower levels of Stepinac’s program, their JV and Freshman seasons went well, their JV turning in an 8-2 campaign, and their freshman turning in a 5-3 campaign. This bodes well for Coach Magee, who will have a good foundation to work from when it comes to the football program. 

Their 2025 League Schedule is below:

Saturday, September 20, 2025	Chaminade
Saturday, September 27, 2025	@ St. Joseph by the Sea
Saturday, October 4, 2025	@ Cardinal Hayes
Saturday, October 11, 2025	@ Xavier
Saturday, October 18, 2025	Kellenberg Memorial
Saturday, October 25, 2025	St. Anthony’s
Saturday, November 1, 2025	@ Iona Prep

With three ‘AA-1’ teams on their 2025 schedule, the Crusaders have a chance to win 3, possibly 4 league games. Their game against Chaminade was close last year, so they may be able to storm back and get revenge. The Crusaders should beat Xavier, Kellenberg, and St. Joseph by the Sea. I would keep an eye on Stepinac this season. They may surprise people. Don’t get last year twisted, this is still a strong program, and last year may have been more of an aberration than an actual trend downwards. 

Iona Prep

The defending ‘AAA’ Champion, the school in New Rochelle has been the class of New York State and the CHSFL for the past four years, going to the championship all four years. This is definitely the best period of Iona Prep football in their long and storied program. With Crew Davis, Julian Guzman, and other studs coming back, Iona Prep is poised for another ‘AAA’ and State Championship run. Their dominance continues. The program is sustainable, as the school is very healthy enrollment wise. Iona Prep’s enrollment is about 1,100 boys from PK-12 grade, with just over 900 in the high school. 

Post Covid, here is their record: 

• 2021: 11-1, W in the CHSAA State Championship vs St. Francis
• 2022: 9-3, L in the ‘AAA’ Championship to St. Anthony’s
• 2023: 8-4, L in the ‘AAA’ Championship to Cardinal Hayes
• 2024: 11-2; W in the CHSAA State Championship vs Canisius
• 39-10 from 2021-2024

Similarly to Stepinac, the future looks bright for the Gaels. Their JV and Freshman team went a combined 16-1 in 2024. With their best players going to their senior year, Iona looks to reload several times in the next few years. They return 2,541 rushing yards, and 35 touchdowns, and Julian Guzman returns with 2,300 passing yards, and 20 touchdowns. Their best player, Crew Davis had 2078 total yards from scrimmage, 1350 rushing yards, and 728 receiving yards on 179 touches, scoring 23 touchdowns. 

Their 2025 League Schedule is below: 

Saturday, September 20, 2025	St. Joseph by the Sea
Saturday, September 27, 2025	Cardinal Hayes
Saturday, October 4, 2025	@ St. Anthony’s
Saturday, October 11, 2025	@ Chaminade
Saturday, October 18, 2025	Monsignor Farrell
Saturday, October 25, 2025	@ Kellenberg Memorial
Saturday, November 1, 2025	Archbishop Stepinac

As they come back as ‘AAA’ Champions, I see a minimum of 5 league wins, with possibly another undefeated league season coming. The Gaels just seem to be hitting their peak, while Cardinal Hayes, Stepinac, Farrell, and St. Anthony’s all have questions moving forward. 

Westchester still seems to maintain its dominance, with two of the best programs in the CHSFL. The 2010s and 2020s has been the time where the balance of power shifted from Long Island, to Westchester and the Bronx. 

Next up, the Bronx.