- April 28, 2026
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Elisa Massaro, a senior and battalion commander for the Lakewood Ranch High School Junior Reserve Officers' Training Corps, is now a member of the Florida Army National Guard.
She joined JROTC to gain discipline and life skills to prepare for her enlistment.
Massaro said she has gained much more than discipline and life skills from JROTC. She noted a few other things, such as strong friendships and support. When her mother, Alessandra Massaro, died in April of last year, she said her JROTC instructors, William Cassidy and Richard Roller, were there for her.
They took the time to check in frequently. She said they provided a safe space for her.
“They taught me resilience when faced with adversity,” Massaro said. “They've taught me to look at the bigger picture and not to get too set back by challenges.”
Cassidy said his father died when he was in middle school, so he has a special place in his heart for students who go through the same kind of loss.
“I know it's hard, but she never missed a beat,” Cassidy said.
Master Sgt. Cassidy has been teaching JROTC for 22 years and has been at Lakewood Ranch High School since 2012. He served 20 years in the Army and retired from service in 1999.
Lt. Col. Richard Roller served 20 years in the Army and finished his career as a military strategist and strategy graduate level instructor. He is the senior JROTC instructor at Lakewood Ranch High School. He began in 2013, left in 2021 and came back in 2024.
Cassidy said being involved in JROTC isn’t just about sending kids to the military, it is about preparing them for the future no matter what path they choose. They teach students to be leaders.
“The mission is to develop citizenship,” Roller said. “Citizenship is the biggest piece, but also understanding critical thinking and creative thinking. Understanding that merit matters and working toward something that's challenging is worth it.”
Both educators are set to retire. Roller will leave at the end of the school year and Cassidy will stay until December to assist in the transfer of leadership of the organization.
Massaro said there is often a misconception that JROTC is strict and you only do things like physical fitness and marching. She said it’s not a bootcamp, but a place to grow into a second family.
“I hope that (with the new leadership), we still keep that structure and that level of discipline, I hope they still provide support to their students,” Massaro said. “I hope (the new program leaders) still want to help students grow as individuals, aside from just getting an A in the class and putting their uniform together properly,” Massaro said.
Roller said every leader brings new insight and energy to the organization. When he returned last year, he was seen as the “new guy” and he appreciated the students’ ability to make the adjustment to learn from a teacher with a different leadership style than his predecessor.
“They're able to adapt to change, understand what the leaders are trying to do, and they're willing to follow it,” Roller said of the students. “At the same time, they are providing their insight into their priorities, because it is their program. We're here to steer them in the right direction, but it's their job to come up with what matters and plan it accordingly.”
Ingrid Pope, a senior, is the public relations officer for JROTC. She said she learned to be louder and more confident, and more prepared for the world.
“They pushed me to aim for bigger things,” she said.
Pope won a three-year national ROTC scholarship for nursing and plans to use it at the University of South Florida.
Jack Crosbie, also a senior, served as the Bravo Company Commander. He will attend the United States Air Force Academy and serve a minimum of five years. He credits Roller and Cassidy for his ability to manage his time, speak with confidence, and take the lead.
“I can look at a problem with two different solutions and weigh the options and see where I want to go,” Crosbie said. “(Roller and Cassidy) have so much experience in leadership fields in their career, and a lot of that will play a big part in what I'm going to do later on.”
Roller said teachers have an important influence on kids, and sometimes it takes years to notice exactly what impact they have had. He said past students have told him that their time together has kept them alive.
