Photos by Jeff Serpa:

Football:

Although it was written 22 years before he was even born, one would have to believe that Eagles’ guitarist Joe Walsh had people like Dylan O’Leary in mind when he wrote and sang lead vocals on the hit song ‘life’s been good to me so far.’

In a recent conversation in which I listed many things that seem to be falling into place in his life, O’Leary humbly acknowledged to this reporter that, “yes, I’m a very lucky man.”

This year in particular has been a special one for the O’Leary family.

His father Tim O’Leary, the well-respected baseball coach at Covina High School led his alma mater and the program to its first playoff win in 20 years, and they followed that with a trip to the CIF-SS championship round for the first time since 1988.

In another first, the Colts also competed in the CIF State So Cal Regional playoffs during their historic postseason run.

Weeks later, Tim O’Leary, along with Glendora’s Jerry Lewallen were named the 210 Prep Sports Baseball Coaches of the Year.

Not that Dylan wanted to upstage his father, but he became the youngest current head football coach in the San Gabriel Valley, when, in March, he agreed to take over the reins at his alma mater.

O’Leary was a three-sport star (baseball, basketball and football) athlete at San Dimas and he graduated in 2019.

Speaking of things going well, O’Leary is now a math teacher at SDHS, and was able to hire an experienced coaching staff that he values, respects and trusts.

In some cases, they double his time on this planet.

The list of men this 25-year-old leader will lean on include Justin Kosik (defensive coordinator/strength & performance), Dillon Corona (offensive coordinator), William Nickell (assistant defensive coordinator/defensive backs), Covina legend Kevin Glaspy (special teams coordinator/running backs), Daniel Robles (quarterbacks), Jordan Taylor (wide receivers), Alex Fuentes (offensive line), Austin Rivea (defensive line), Mike Caceres (linebackers) and Greg Saris (corners).

O’Leary said the lower-level coaches are just as important to the program, and he’s happy to have Danon Palmer, Isaac Loboto, and Elijah Parris in place to help develop their younger players and preparing them for the varsity level.

Tim and Christi O’Leary did an incredible job raising this young man and his siblings.

His priorities and values match well with his long-term ambitions.

O’Leary earned his bachelors and masters degrees at UCLA and the University of La Verne, respectively.

As mentioned, O’Leary is significantly younger than his peers in the SGV, but that doesn’t bother him one bit.

Part of that maturity in not caring what others may think or say about him or the SDHS hire comes from the old adage of only concerning oneself with what we can control and letting the excess noise disappear into thin air.

Dylan spent the last 25 years sitting across the dinner table from his father and their conversations from A-to-Z about sports has been an educational process for this young man.

His first coaching experience came at age 14, where he helped his grandfather, Jack O’Leary with his 10-U baseball team.

O’Leary also spent time at San Dimas during the COVID-19 pandemic under his predecessor and his former coach, Mark Holman.

Over the last four years, Dylan served loyally at South Hills and he has to utmost appreciation for the opportunities provided to him by someone this writer considers one of the area’s best young coaches, Jacob Calderon.

While Dylan O’Leary won’t even be 26 until December, this dude is as old-school as they come.

His genuine belief system prioritizes classwork and becoming a solid and respectable young man over wins and losses.

In many ways, he’s inspired by Mark Carson and the way Rio Hondo Prep conducts its business.

That little school in Arcadia has won three consecutive CIF-SS championships in Division 9, 7 and 5, respectively.

More importantly, the Kares represent their school, program and families with the utmost class and dignity.

And they never disrespect an opponent or the game of football.

Dylan is so serious about being a class program that he asked this writer to please stop by a game or two at SDHS and give him feedback as to how the San Dimas sideline is conducting itself.

Unlike some leaders in high places, the buck stops with Coach O’Leary.

If the program fails at anything, he’ll take the blame.

When they succeed, he’ll deflect the credit to his players and the staff.

He’s already proven his pledge to be as helpful to the media as possible in the hopes of getting his players the recognition they will earn.

Although they’ve been successful overall, the Saints are 0-for-13 of late in rivalry games.

Steve Bogan and Bonita went 7-0 head-to-head with Holman, and Marcel Perez and Northview won each of their last six games against SDHS.

In fact, the last time the Saints beat the Bearcats, O’Leary tossed a TD pass in the 19-8 victory back in 2017.

The Smudge Pot rivalry game will continue in 2026, but unfortunately the late-season Valle Vista League showdown between San Dimas and NHS is a thing of the past.

The Vikings open play in the Sierra League this year.

O’Leary intends to feature a more balanced offense than SDHS opponents are used to seeing.

The value of being able to run and pass the ball is obvious to one’s success, but a program’s ability to keep elite athletes (quarterbacks, tight ends and wide receivers) at home because they’re actually being featured can not be overstated.

“We’ll get the ball to our best athletes in space and utilize their skills,” O’Leary said. “We want to be as balanced as possible and give as many players the opportunity to shine in our system. I’m in the business of creating good people, as opposed to just winning football games. I’d rather go 0-10 and have nothing but good people who work hard and do all the right things rather than going 10-0 and have a sideline full of selfish, classless or lazy players and coaches. We want to provide life lessons and an example for our young men and help prepare them to be quality husbands and fathers.”

O’Leary wanted to emphasize how much he desires making San Dimas home football games a community event.

Coach O’Leary invites all Saints students past and present to attend Thursday’s season opener against their visitors from Glendora.

O’Leary is deeply grateful to the SDHS administration for giving him the opportunity of a lifetime at the school he loves.

If San Dimas is to have a successful season, you’ll likely see these names and others playing critical roles: Jacob Gallegos (WR/RB/DB), Liam Loyola (RB/LB), Devin Gonzales (OL/DL), Michael Baeza (WR/TE/LB/DL), Adam D’Amato (RB/DB), Raymond Armenta (RB/DB/LB), Aiden Castro (WR/DB), Landon Castaneda (WR/DB) and quarterback Kris Saris.

Jacob Gallegos had a monster junior season in 2025.

He carried the ball 213 times for 1,668 yards.

That included 16 rushing TDs.

He also led the Saints in receptions (13), receiving yards (351) and TD catches (4).

Liam Loya tallied 407 yards on 57 carries and three scores.

I asked two of their studs, Michael Baeza and Jacob Gallegos to answer the following: 1) What’s the excitement level like at SDHS and if they’re capable of competing for a VVL title. 2) How has the new staff been accepted and what do they appreciate about the way Coach O’Leary and his staff conduct business:

Said Michael Baeza: 1) “We definitely have a lot of excitement for this season, and we have a lot of athletes on our team that are gonna make a difference for this year. Everyone is playing real confident. We all balled out in our 7-on-7 events, and it’s getting better everyday as we put the pads on. We have a solid group of guys, and if we play with confidence and trust in our coaching staff, we can definitely compete for a VVL title.

2) Everyone is happy with the new staff. They have us work hard and they believe in us. We have good and positive energy with our coaches and teammates and we are all really excited for this season. What I like about our coaches is they bring a lot of good energy to the team and they motivate us to play the best to our ability. They are as excited for the season to start as we are.”

Said Jacob Gallegos: 1) “The excitement level is extremely high, both for the coaches and players. We have a lot of talented guys coming back, and everyone has been working hard and competing every day in practice. We definitely believe we have the talent to compete for the VVL title, but we know we have to earn it every week. Our goal is to keep getting better, stay together as a team, and see how far we can take it.”

2) Coach O’Leary has been amazing and a great leader all around. Everybody seems bought in, and there’s a lot of positive energy around the program. What I like most is how much the coaches communicate with us and how competitive they make practice. They expect a lot from us, but they also make you want to play hard for them.”

Another person this site is excited to work with is SDHS athletic director, Diane Chiappone.

She sent thoughts on the hiring of the 25-year-old O’Leary.

“We were thrilled to hire alumni Dylan O’Leary as the next head football coach at San Dimas High School. Throughout the interview process, Dylan demonstrated a clear vision for building a program founded on character, accountability, and competitive excellence. Although young, his poise and maturity set him apart in the interviews.

His passion for mentoring student-athletes and his commitment to fostering success both on and off the field made him the outstanding choice to lead our football program. I believe Coach O’Leary will be an integral piece in my goal to building a stronger athletics program. We are confident that Coach O’Leary will have a lasting, positive impact on our students, our team, and the San Dimas community, and we look forward to the future of Saints Football under his leadership.”

Lastly, I asked many of O’Leary’s staff to answer the following:

1) What makes you comfortable that a 25-year-old man is ready to be the youngest head football coach in the SGV? 2) What impressed you about Dylan? 3) What made you want to be part of his staff? 4) Has Dylan made you feel like your input will be valued?

Said Kevin Glaspy: 1) “Age and experience are important, but Dylan has the “it” factor as a young coach. He’s blessed with a great personality. You immediately know he’s a genuinely caring person, he is a very quick learner, and he is hungry to continue to grow and learn. 2)He has a great presence at practice. His energy is contagious and he really loves San Dimas football. He’s one of the best young leaders I’ve ever worked with. His level of maturity and professionalism is way beyond his years, and that alone is impressive.

3)I’ve known Dylan his entire life and he’s essentially like a nephew to me and for the past few years we’ve been on opposite sidelines. When this opportunity came to join forces and try something different I had a good feeling we would work well together. I felt Dylan could get a staff together that could have the same vision as himself moving forward at San Dimas. One of Dylan’s best traits is that he is a good listener, but he’s also in charge. His job isn’t to make us happy but to facilitate all of his resources to make the best decisions for the team. All of us coaches know that and we trust each other and Dylan as our head coach.”

Said Justin Kosik: 1) “Coach O’Leary is not your regular 25-year-old. He truly is an old soul. His organization, planning, communication, and energy he brings are all exceptional. And he doesn’t lead with an iron fist. He’s approachable. He’s a player’s coach. And best of all, he leads with integrity. 2) Coach O’Leary’s energy level, knowledge of the game, and his eagerness to learn everything he can about coaching young men to be the best versions of themselves is incredible to witness.
3) When Coach O’Leary first presented me with this opportunity, I loved the idea of being the Defensive Coordinator and Strength and Performance Coach again. I was excited for the vision he has for the boys and the program, as well as his eagerness to learn and lead.

Plus it brought me back to San Dimas which will always be special for me since my wife graduated from there and worked there for a very long time. 4) Most definitely. With my tenure as a coach, I have pretty extensive coaching and athletic admin knowledge that he has already capitalized on. Coach O’Leary welcomes input from all of his coaches, and I love the fact that he communicates consistently and effectively with us. I know that if I have a suggestion, he will always listen to my ideas and then ultimately do what he feels is best for the team, and I will back him 100%.”

Said Dillon Corona: 1) “His energy, work ethic, and willingness to surround himself with good people give me confidence that he’s ready for this opportunity. 2) What impresses me most is his passion and commitment to doing things the right way. He cares about his players and coaches, holds himself to a high standard, and is always looking for ways to improve. He’s not afraid to listen, learn, and make adjustments when necessary. 3) I wanted to be part of this program because I believe in Dylan’s vision. He wants to build a culture based on accountability, hard work, and relationships. 4) Absolutely. From the beginning, Dylan has made it clear that he wants collaboration and open communication between not only between Him and I but amongst the whole staff.”

Said William Nickell: 1) “Dylan isn’t an average 25 year old. He is mature beyond his years and has rich coaching experience. With the help of veteran staff members, O’Leary has more than proven so far that he is up for the job with his organization, hard work, and creating a culture that promotes competitive natures and positivity
2) Dylan hasn’t blinked once since he has been hired. He has surpassed every road block he’s hit without hesitating or complaining. He also does a great job with holding himself and his staff accountable. 3) As a young coach, I wanted to learn what it takes to take the next step at a young age. Dylan also values the thoughts of his staff which was very compelling for me. 4) Dylan has absolutely made me feel like my input will be highly valued. Before making decisions he frequently reaches out to the staff to offer their thoughts and put them into consideration.”

To view a photo gallery of a 7-on-7 game by Jeff Serpa, click on the Facebook link here: Facebook

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2026 San Dimas Schedule:
8/20: Glendora at SDHS
8/27: SDHS at Chaffey
9/3: SDHS at Colony
9/11: SDHS vs Bonita
9/18: SDHS at Western
9/25: Bye Week
10/2: SDHS at Alta Loma
10/9: SDHS at Diamond Ranch
10/15: Chino at SDHS
10/23: Claremont at SDHS
10/30: Los Osos at SDHS

Valle Vista League Standings in 2025:
Alta Loma (8-3, 4-1)
Northview (8-3, 4-1)
West Covina (7-4, 4-1)
San Dimas (7-6, 2-3)
Baldwin Park (8-6, 1-4)
Diamond Ranch (3-7, 0-5)