Jason Olson Obituary: Ocoee High School Teacher Remembered for Making History Fun and Inspiring Students
Jason Olson Obituary, OCOEE, Fla. — Jason Olson, a beloved teacher at Ocoee High School, is being remembered by former students and colleagues following his passing. Those who knew Olson have shared tributes describing him as a caring educator, a supportive friend and someone who made a lasting impression on the people around him.
Former students have remembered Olson not only for his role in the classroom but also for the personal connection he built with those he taught. One former student recalled Olson as one of her favorite teachers at Ocoee, saying he was more than a teacher because he genuinely cared about his students and made history enjoyable.
Among the memories being shared is Olson’s tradition of celebrating students’ birthdays. According to a former student, he would play a birthday song for students in class, creating moments of laughter and happiness that remained memorable even after graduation. The former student said Olson would occasionally send the same birthday song on Facebook after she had graduated, and she would return the gesture on his birthday.
Another tribute described Olson as someone whose presence could make people feel special and seen. Cathy Cannon, who said she worked alongside Olson at Ocoee for more than a decade, remembered him as being like a brother and spoke of his deep laughter, uplifting smile and genuine personality.
Cannon also remembered Olson as an amazing teacher and an exceptional friend, describing him as one of the purest souls she had known. She recalled one of Olson’s expressions, calling him “the bee’s knees and the cat’s pajamas,” a phrase that reflected the personality and humor those close to him associated with him.
Former students have also taken to social media to express their grief. One former Ocoee High School student recalled Olson as the best and coolest teacher she had in high school, remembering how he shared rock music with students on their birthdays and continued the tradition on social media after they graduated.
The tributes paint a picture of an educator whose influence extended beyond the classroom. Through humor, music, birthday traditions and genuine care for his students, Olson created memories that former students continue to carry with them.
Details regarding Olson’s age, cause of death, family members, funeral arrangements and memorial services were not provided in the information available for this report. As former students and colleagues continue to mourn his passing, the memories being shared reflect the lasting impact he had on the Ocoee High School community. May his memory be honored by the many students, colleagues and friends whose lives he touched.

