When Jonathan “JP” Iasillo joined Peekskill’s soccer program 20 years ago, he set out on a mission to transform Peekskill soccer into a powerhouse. Thanks to his unwavering dedication, today the Peekskill boys soccer team is one of the strongest teams in the local area.

In 2014, Iasillo became the head coach of the Peekskill Varsity Boys Soccer team, after stints as the modified and junior varsity coach. During his decade in charge, Iasillo has led the team to an impressive 94 victories.

This past season, Iasillo enjoyed his best campaign to date with a record of 14 wins, three losses, and two draws. The varsity soccer boys made history this year, becoming the first Peekskill boys soccer team in over 40 years to reach the semi-finals of sectionals. Unfortunately, the Red Devils were knocked out of sectionals in the semi-finals by a strong Fox Lane team, who beat Peekskill 3-1.

“We thought we had a good game plan going in but that’s how the game goes sometimes,” said Iasillo when recalling the loss. Regardless of the heartbreak that evening, Iasillo continues to be positive about the future. The coach said he would like to continue to coach the Peekskill boys varsity team for as long as possible.

JP’s early years 

Jonathan Paul Iasillo, 47, grew up in White Plains. But to his family, he was known as “JP.” “Growing up there were a lot of John’s in my family, so I had the nickname of JP, as opposed to big John or little John, who was my uncle and my cousin,” explained Iasillo. To this day, Iasillo is still referred to as “JP” by many of his colleagues and students.

Fitness has always been an important part of Iasillo’s life. “As a kid, I enjoyed sports and staying active, whether that was playing sports in the neighborhood or organized teams.” While Iasillo played a handful of sports, he always gravitated towards soccer.

From elementary through high school, Iasillo played on a White Plains youth travel soccer team, starting off as a forward, the main offensive position in soccer. But when he got to middle school, Iasillo realized the glory of defense by fluke. Filling in for his team’s injured goalkeeper, Iasillo put on gloves and stepped in the goal. From that moment, Iasillo cemented himself as a permanent goalkeeper for the rest of his amateur soccer career.

In addition to travel soccer, Iasillo played three years of varsity soccer for White Plains High School. After graduating from high school in 1995, he attended Slippery Rock University in Pennsylvania, playing four years of college soccer at the Division II level for the men’s soccer team. He graduated in 1999 with his bachelor’s in Physical Education.

After returning home, Iasillo began searching for a job. He found a job listing for a physical education position in the Peekskill City School District. Although unfamiliar with the area, Iasillo applied and was hired as a substitute for Uriah Hill in the spring of 2000. A few months later, Iasillo was hired as a full-time teacher starting in the fall of 2000.

During Iasillo’s early years within the district, he taught morning classes at Uriah Hill and afternoon classes at the Peekskill Middle School and Hillcrest. In 2009, Iasillo settled permanently, along with the students, into the newly built middle school. 

Recalling this monumental move, Iasillo said, “It was pretty crazy to see – just unbelievable.”

“A new gymnasium much larger in size, a new pool, it was exciting times for everybody,” he added. 

Over the years, the Peekskill Middle School has seen an influx of new students. “In terms of numbers, the city has really grown, so there’s a lot more kids in the middle school now.” Iasillo says he’s happy to see the population of the school has become more diverse from when he first joined. 

A coach is born 

Before becoming a coach within the Peekskill City School District, Iasillo had little to no experience running a soccer program.

In high school, Iasillo coached a recreation team for community service hours and after college, he trained young athletes in summer soccer camps. Although unproven, Peekskill took a chance on Iasillo in the early to mid 2000’s, putting him in charge of reviving a struggling modified program.

The modified level is one of the most important stages in a young athlete’s journey: young athletes perfect their game, while learning the skill and discipline required to strive at the high school level. While Iasillo had the determination and love for the sport needed to coach developing players, he encountered a problem early into his coaching career. He had no players.

Nearly 20 years ago, soccer was one of the least played sports in the city. Iasillo recalled finding it very difficult to get enough players to join his team when he was the modified coach. “Not many kids were playing soccer when I first started. I had to recruit some of the kids that weren’t doing any fall sports.”

At the time, basketball and football were everyone’s favorite sports, explained Iasillo. Both programs had a history of success and tons of fans. But rather than let the lack of interest in soccer derail his aspirations, Iasillo used it as fuel and slowly began to climb the ranks within Peekskill soccer.

Now, partly because of Iasillo’s success record, soccer has become the most popular sport amongst kids in Peekskill. To accommodate the growing number of interested students, the district recently formed a second modified and junior varsity boys soccer team.

Coaching the Junior Varsity and Varsity teams

After two years of working at the modified level, Iasillo became the boys junior varsity soccer coach around 2009. Iasillo says making the jump from modified to junior varsity was great, but he instantly noticed the difference in quality. “Everything was different. The number of games played, the commitment required, the kids showed more passion and more of a competitive nature, and even the speed of the game was quicker.” Iasillo enjoyed a fruitful four-year stint as junior varsity head coach, enduring many ups and downs in the process. In 2014, Iasillo replaced Anthony DiCuio as head coach of the boys varsity soccer program.

In his first year, Iasillo led Peekskill to the first round of sectionals by pulling off an upset victory over Keio (Purchase, NY) in an outerbracket game. Iasillo says this accomplishment meant a lot to him because it got people talking about Peekskill.“That win was when we knew we were taking a step in the right direction,” he said.

Immediately after taking over, Iasillo began to change the team’s culture, introducing new practice routines and prioritizing team communication and bonding. “When I took over, we began to hand out practice shorts. The boys had to be in contact with each other and decide what color shirt they were going to wear.”

“It made them talk off the field,” he added. Iasillo says this and a few other changes helped the boys feel more comfortable with one another, becoming a tight knit group.

Iasillo also noticed his players lacked guidance and tips on how to succeed at the collegiate level. So he started bringing alumni players to speak to his teams during the season. He has continued this tradition every season and says his players appreciate hearing from people who were once in their shoes.

The following year, in 2015, Iasillo was named “Coach of the Year” by his peers from the Section 1 Boys Soccer Coaches Association. That season his team finished with a record of 10 wins and seven losses.

While making it to the first round of sectionals in his first year was an impressive feat, Iasillo and his boys struggled for several years after to make it past the outerbracket and first round games. In 2022, Peekskill was knocked out in the first round of sectionals by Pearl River on penalties. The following year, Peekskill was eliminated in the first round of sectionals by Fox Lane in a 3-2 loss in overtime.

For a while it seemed like the first round of sectionals was Peekskill’s glass ceiling, but that at all changed this year. The 2024 season will be remembered in Peekskill history as one of the best campaigns a boys soccer team has had. Throughout the season, Iasillo’s team consistently put on impressive performances, easily dismantling almost any opponent that stepped in their way. The team finished the regular season in second place in Class AA.

During their postseason run, Iasillo’s boys were finally able to make it past the first round of sectionals by beating Gorton, 3-0. In the quarter-finals, they strolled past Riverside in a 5-1 victory. Peekskill’s historic campaign came to an end in the semifinals, when they were eliminated by Fox Lane.

Iasillo says he is extremely proud of what the boys were able to accomplish this year and can’t wait to see what future teams will produce going forward. “These guys set a standard, so now the next guys coming up know what we’re aiming for.”

Peekskill’s 2024 squad also has the unique distinction of having the best record in Iasillo’s 10 years leading the soccer program. They finished their season with a record of 14 wins, three losses, and two draws. Prior to that, Iasillo’s 2021 squad held the best record with 11 wins and six losses. 

According to Iasillo, one of the biggest factors contributing to their success this year was the team’s participation in a summer league.

Pre-season for varsity sports can be very demanding because of the short window (sometimes only a week or two) teams have to condition and practice before the commencement of their season. Because of this, it has become common for many local varsity soccer teams to participate in summer leagues, to keep players sharp. However, the Peekskill team had never taken part in these leagues until this year. All returning varsity players and interested players were invited to participate in the summer league, which took place in early July with eight other schools.

“The summer league helped a lot because we got to develop chemistry and work on conditioning. It’s very hard to get fit in six days, so them playing for a good four weeks together kept them extremely fit,” said Iasillo.

After seeing first hand the benefits of the summer league, Iasillo says he would like to continue to offer this every season if there is enough interest.

Another important factor for the success of the Peekskill boys varsity program is assistant coach Jaime Guevara. Guevara, who grew up in Peekskill and played for the boys varsity soccer team, has been helping Iasillo run the program since 2017. “Jaime’s great. I consider him family,” said Iasillo.

Iasillo praises how Guevara is able to help integrate players into the team with his bilingual abilities.  “We have a lot of players who come and English isn’t their primary language and he’s able to help with that bridge to help them succeed and join the team.”

Coach Anthony DiCuio, who has worked with Iasillo for over 20 years, noted the care and dedication Iasillo demonstrates every year.

“He is meticulous in his preparation for each season, each practice, and each game. He fosters positive relationships with his players and helps teach them the maturity needed to become young men.”

“He saw the program and soccer families through some rough times over the past few years and I cannot think of anyone who could have handled it better. His commitment to the program and the community will continue to yield positive results for as long as he’s at the helm.”

Looking back over the years

Iasillo has had the privilege of coaching hundreds of young talented athletes over the years. One player that has stood the test of time for Iasillo is Oswald Annang. Annang was Iasillo’s first player to receive an All State recognition in 2016. Annang also received All Section recognition in 2015, 2016 and was named League Most Valuable Player in 2015 and 2016. Annang holds the record for most goals in a season with 29. Annang currently plays for the Baltimore Blast, an American professional indoor soccer team based in Baltimore, Maryland. 

This year, Iasillo has been impressed with several players on his roster, but none more than Umaru Conteh. The senior forward received All-League, All-Section, League MVP, and All-State recognitions at the end of the season. Conteh came close to reaching Annang’s record this year, finishing the season with 25 goals. 

Throughout his time as head coach, Iasillo has addressed challenges with the same care he puts into coaching, always putting the students first. Until this year, students in grades 9 through 12 all tried out together for a spot on either junior varsity or varsity during tryouts held in the summer. For the last few summers, Iasillo began to see a rise in interested students, consistently reaching close to 80 kids.

“It was hard to get an individual’s evaluation,” said Iasillo of the last few tryouts.

To mitigate this issue, this year Iasillo and his colleagues split up tryouts into two separate sessions. First-years and sophomores tried out together in the early afternoon and juniors and seniors tried out together in the evening. Iasillo, who was present for both sessions, says this new approach allowed coaches to better evaluate every single player.

Due to the extensive amount of talent on display during tryouts, Iasillo kept 23 players this year, instead of his usual 20-22 players. Iasillo hopes to continue his new tryout routine as soccer continues to grow in popularity in Peekskill.

Another challenge for Iasillo was the field his team played on. Prior to the construction of the new turf field at Torpy Field in 2021, Peekskill was one of the very few schools in the area that still played on a grass pitch. When Peekskill played away on turf fields, the team had to change their tactics and take into account the speed at which the ball travels on turf. But when they played at home on grass, they had to adapt their style to accommodate the poor conditions of their field. This became very difficult for his players, Iasillo noted.

“We had to play through tough conditions. Between the bumps, the holes, and when it rained – the huge puddles.” When his team was finally allowed to use the turf field at Torpy, Iasillo says he instantly saw a difference in how his boys played. 

“Ever since we got that built, it’s been great.” He adds that his team no longer have to worry about their performances being affected by inconvenient weather because the turf doesn’t deteriorate like grass. 

Iasillo’s most difficult challenge was helping his students navigate through their grief after the deaths of two soccer players. In 2020 and 2021, the Peekskill Athletic program and community tragically lost two former Peekskill varsity soccer stars in Joaquin Salazar and Liony Santos. “I think that was one of the hardest things as a coach to go through and see your players go through,” recalled Iasillo. 

“Both were great young men that loved the game. They came from two great families. They had everything, the speed, strength and desire to play at the collegiate level. They passed away way too early.”

In May 2021, the Peekskill boys soccer team played a memorial game for Salazar. At this event, Iasillo presented Salazar’s family with flowers and his jersey, before giving emotional remarks.

Shortly after the passing of Santos in July 2021, the Peekskill City School District opened the middle school for students and families to meet with counselors. Family, friends, and coaches including Iasillo, all spoke on Santos at this event. Iasillo consoled various students during this period of mourning. 

In memory of both players, angel wings were added on the sleeves of the new uniforms the Peekskill boys wore throughout the season. Iasillo says another way the district could look into remembering both players is by adding a plaque or tree by the flag at Torpy Field. 

“They’re always going to be with us.”

Life as a Physical Education teacher

Physical Education teacher by day, head soccer coach by night, if you ask Iasillo he’ll tell you he’s living the dream.

“I love athletic sports and exercise so to combine those two –  they’re the perfect jobs for me.”

As a PE teacher, Iasillo says he loves that his class is a positive space for students to let loose during the school day. “For most of the school day, unless they’re going from class to class, they’re sitting. PE is one of those classes, where they get to socialize. They have tons of energy and they want to be moving.”

In addition, Iasillo says he enjoys interacting with students and helping students develop a love for fitness and themselves. 

“Sometimes a child may not know how good they are at something and they just need that little confidence to give it a try and next thing you know, they’re excelling at it. It’s always great to see kids develop the physical skills and strength, but more so confidence and self esteem.”

Just like any other class, a lot goes into planning courses for physical education. Iasillo states that courses taught at the middle school are based on a curriculum developed by him and his colleagues. Units center around swimming, hand-eye coordination, foot-eye coordination, climbing, and more. 

“Hand-eye coordination is volleyball and football. Foot eye coordination is soccer. The pool is used for swimming classes. During the winter season, students do climbing that involves risk taking and problem solving,” Iasillo explained. 

A lot of the units and course material offered also have a focus on organized sports, so if a child has an interest and is excelling during class, coaches are able to recommend the school’s modified program. 

Iasillo believes that although PE classes have changed over the years, there are still a lot of misconceptions about the course. 

“I think some people associate gym class activities with things like dodgeball and really competitive contact sports, but we offer more than that.At the middle school, we focus on fitness, team sports, cooperative games, team building activities.”

Having kids exercise for forty minutes is great, but for a kid to enjoy a healthy life, they need more. That’s why Iasillo says that he and his colleagues are always suggesting fun programs students can participate in.

“As PE teachers, we’re always trying to put the word out about where to play, whether that’s rec basketball or local soccer agencies that are looking to do a few training sessions.”

Iasillo is proud to see the expansion of youth sport opportunities within the city over the past few years. Whether it’s varsity, junior varsity, modified, recreational programs, or the new Peekskill 46 program for students in grade four to six, there’s something for everyone, says Iasillo. 

Over the 20 years that Iasillo has served the district, he has cherished many moments with students. One of his favorite memories involves a student who improved his swimming skills thanks to the courses offered at the middle school.

“When he came back his eighth grade year, he told me ‘I was so happy this summer. I got to go to the water park and go on all the rides’. I remember that made me feel so good because there are moments when you’re teaching and you hope you’re instilling the information but you don’t know.”

While interest in physical education hasn’t decreased over the years, Iasillo says new distractions have begun to affect the enjoyment of PE and the desire to participate. “For kids nowadays, there’s a lot for them to do, like electronics, video games, social media.”

“When I first started teaching, cell phones weren’t much of an issue. Electronics and screen time – kids love that, which is fine but everything in moderation. For our class, we try to give them that break, where they can get 40 minutes of movement to help them physically, mentally and emotionally.”

Iasillo says for the most part, students are good about participating in class. However, sometimes a student refuses to engage in course material at all. In those scenarios, Iasillo says he and his colleagues take the appropriate measures to make sure the student is doing okay. 

“If the child has a difficult time participating, we reach out to home and the guidance department and maybe check on the child to see if something is bothering them.”

Although Iasillo has been with the Peekskill City School District for the past 24 years, he does not see himself slowing down anytime soon.

Outside of work

Iasillo is married and is the proud father of three young children. When asked about what it’s like being a father, Iasillo responded “There’s nothing like being a father. I can have many titles, but for me, only three people call me dad.”

All of Iasillo’s children have continued in his footsteps and play soccer. “They didn’t really have much of a choice,” he laughed. 

When he’s not working, Iasillo says he enjoys playing soccer in the backyard with his kids, bike riding, landscaping, walks, listening to music, long drives, and spending time with his family. Iasillo also likes watching soccer.

“If I’m able to get the TV when my kids aren’t hogging it, I watch Napoli and Manchester United whenever possible.” 

During the school year, Iasillo performs several duties like being a physical education teacher, soccer coach, and an intramural supervisor. Iasillo says he couldn’t do what he does without his wife.

“It’s tough between work and coaching. I give my wife a lot of credit, she does all the duties, getting them where they need to be.”

What’s next?

In Iasillo’s eyes, success isn’t measured in titles. For Iasillo, success is measured in consistently showing improvement. If you asked anyone 10 years ago if they thought Peekskill could challenge for the Section 1 Class AA championship, they’d laugh at you. But now, Peekskill is a team that can cause serious damage and is expected to keep going forward. 

After this year’s remarkable season, Iasillo has set a new goal for himself before he steps away as head coach. “Winning the league would be great. It’s been a very long time.”

His method to achieve this is simple, he says. “I just want the players to play their best ball. If we focus on that, the results will come.”

If Iasillo is able to repeat the success he had this year, he will not have a problem hitting a milestone of 100 wins next season. “Hopefully, I’ll be approaching that next season, but we’ll see. Like I tell the players, one game at a time.”

However, when the 2025 season rolls around, Iasillo will need to rebuild his squad because he will lose 19 seniors from this year’s team. Iasillo seems unfazed by this challenge and says he’s already planning for next season. “Next year should be fun,” he said.

Iasillo revealed that he would like to head the Peekskill Varsity Boys Soccer team for many more years. “I could coach another 10 years or even more.” 

“Coach Iasillo has been a consummate professional. Besides being a terrific soccer coach, he goes above and beyond for our students. Coach isn’t just the varsity boys soccer coach. He is a leader, mentor, and teacher to many. We are fortunate to have him as a part of our team and district,” said Athletic Director Austin Goldberg when reached by the Herald.

24 years working as a physical education teacher in the district, 10 years as head coach of the boys soccer team, and years of heading many athletic programs within the middle school, it’s fair to say that Iasillo will go down in history for his many contributions to Peekskill Athletics.