For the Love of the Game: Castilleja Launches Its Inaugural Flag Football Team
It’s dark out. There’s a chill in the early morning air, and the lights are still on around the Circle. But a group of 30 students in red and white jerseys are already warming up.
These are Castilleja’s pioneer flag football players, with no trace of sleepiness on their faces. They’re here nearly every Monday morning, ever since the school launched flag football as an official sport this fall.
The purple sky fades into blue, dappled with pink cotton candy clouds.
“I want you to do a five yard out!” instructs Matt Callahan, English teacher during the school day and football coach before and after. The players in red jerseys line up on the grass.
“How are you supposed to line up? Like this,” another coach, Steve Rochlin, tells his defense in white. (In addition to volunteering as a flag football coach, Rochlin coaches Castilleja’s lacrosse team and Paly’s tackle football team). He bends his knee to demonstrate the proper stance.
“We’re in man coverage,” Coach Rochlin instructs. “I want you guys to hold their jerseys, so you get used to running the pattern with them, so you understand how close you have to be.”
Meanwhile, Coach Callahan regroups the offense. “Okay, let’s do it!” he says. The players take their positions on the field. A whistle, and the play begins, fierce and fast.
Yet there’s something unique about this team. Whenever someone catches the ball, the entire team erupts in a cheer. They clap for one another and smile.
Girls’ flag football has been gaining momentum ever since CIF (California Interscholastic Federation)’s Federated Council, the governing body for high school athletics in the state, approved it in 2023 as a sanctioned sport after years of deliberations, joining states like New York, Nevada, Florida, Alabama, Georgia, Alaska, Arizona, and Illinois. Unlike tackle football, flag football does not permit tackling, diving, or blocking. In order to “tackle” the opponent, a player must pull off a fabric flag from the opposing player’s belt.
As soon as Castilleja offered flag football this year, 30 Upper School students signed up, constituting an impressive 13% of the student body. In addition to coaches Callahan and Rochlin, the team also gets support from two more committed coaches: parent volunteer coach James Hall and math teacher Steven Lai.
“It speaks to the community that sports bring together,” says Coach Callahan. “I get to connect with students in a way that's not about English. I get to see them be virtuosic in a completely new kind of way.”
Mr. Callahan played football when he was in high school and college; he also played rugby and coached football recreationally while teaching abroad in France. At some point, he stopped playing. “I shut that part of my brain down,” says Coach Callahan. That is, until Castilleja’s whispers of the inaugural team began last year. He agreed to coach, and the love of the game was quickly reignited, he says. “Now I’m thinking about football all the time!”
“They’re really smart and there’s a lot of laughter,” says Coach Callahan “The growth is exponential from week to week and even from practice to practice. I see a lot of positive influence that the kids have on each other. The team atmosphere is so nurturing. And it is competitive and it is fast. Football is all about trusting every person on the team, and these girls really get that.”
The other day, before a game, a running back looked at her team and said, “I love you guys!” remembers Coach Callahan. “That, to me, is the heart of team sports.”
Sophie P. ’25 and her classmate Camryn N. ’25 worked with school leadership to help start the team. Last year, the two sent a survey to classmates to see if they could reach critical mass. They did.
“I knew I really wanted to play and be a part of the beginning of the program,” says Sophie, who plays mainly safety on defense.
Her teammate, Lila C. ’25, has been playing softball for 10 years. “I thought it would be fun to transfer that skill to a new sport. My dad is a really big football fan, so I’ve grown up watching it every weekend,” says Lila, who plays defense and who’s an avid 49ers fan. “It’s nice to see the sunrise every Monday,” she adds. “It does make you feel a lot more productive.”
Meanwhile, Sabella V. ’28 got interested in flag football after trying it as an 8th grader for a three-week mini-season last spring. That mini-season proved so influential that 13 students ended up joining this new official team as freshmen, with five of them experienced enough to be everyday starting players. “We’re all kind trying to find our place within flag football and we’re all trying to help each other improve,” says Sabella, who plays defense, linebacker, and corner.
Cali S. ’26, one of the four team captains, feels a special affinity for flag football, unlike with other fall sports she’s played before. “They weren’t really my type of sports,” she explains. However, she’s always enjoyed catching and throwing the ball in P.E. “I thought it was really exciting that we would get to play that against other teams, that it was a serious Casti sport.”
Whenever Cali wakes up at six in the morning for practice, she and another teammate text each other “Good morning,” and they’re ready to go.
Recently, the team organized a juice tasting party, a scavenger hunt, and an overnight bonding retreat in Santa Cruz, coinciding with a tournament. “We’re the ones who have to be making these traditions,” Cali says. “I’m a person who cheers a lot. I’m always firing everybody up. Especially as a captain, if your energy is up, then everyone else can feed off of that.”
The sun is finally out and the practice is over. Players gather in a circle and share gratitude. Someone is grateful to a teammate for playing offense. Another is thankful for everyone’s good spirits.
“I’m proud of you guys. Great practice!” says Coach Callahan. And with a cheer, “One, two, three, Gators!” the players clap in unison and disperse to their morning classes.
As the season draws to an end, Coach Callahan is eager to keep the team going next year, he says. “I don’t see a way out of it!"
