For more than 35 years, Nickolas Grasso inspired transformation in Florida high school athletics, guiding generations with visionary leadership and a steadfast dedication to the success and well-being of student-athletes. Esteemed as an administrator, coach, and mentor, Grasso has served in distinguished capacities at the local, district, and state levels, significantly advancing the mission of interscholastic athletics in Florida. His distinguished career includes serving as President of the Florida High School Athletic Association’s Board of Directors, President of the Pinellas County Athletic Conference, and President of the High School Principals’ Association. Beyond these statewide contributions, he has left a lasting impact as a head coach, collegiate coach, Pinellas County Schools Athletics Director, and Principal of Clearwater High School. Through each role, Grasso has championed educational athletics, fostering excellence, integrity, and opportunity for countless students across Florida.

Grasso began his career in coaching, serving as the baseball head coach and junior varsity football coach at St. Petersburg Catholic High School from 1982 to 1984, and later in the same roles at Boca Ciega High School from 1984 to 1987. Transitioning into school leadership, he served as assistant principal at Dixie Hollins High School from 1992 to 1995 before being named Principal of Clearwater High School, a position he held for 11 years (1995–2006). Under his leadership, Clearwater captured three state team championships (Girls Volleyball in 1997 and 2000, and Boys Soccer in 2001) along with five state runner-up finishes and hosted the inaugural Girls Flag Football State Championship.

From 1998 to 2004, Grasso served as President of the Pinellas County Athletic Conference, providing guidance and leadership to school athletic programs across the county. He also served on the FHSAA Board of Directors from 2001 to 2006, including a term as President from 2003 to 2004. In 2006, Grasso was appointed County Athletic Director for Pinellas County Schools, a role he held for 11 years until 2017. During this time, he was an active member of the Florida Interscholastic Athletic Administrators Association and played a key role in leading Pinellas County Schools to three state titles in the Commissioner’s Academic Challenge (2008, 2013, and 2017).

Beyond his administrative leadership, Grasso worked tirelessly to improve the professional and personal lives of coaches and student-athletes. He was instrumental in advocating for increased pay supplements for coaches in Pinellas County. He also implemented at the annual Pinellas County Coach of the Year Awards Banquet, “Coach of the Year” rings, to honor the county’s top coaches and fostering a greater sense of community and support for athletics. At the state level, he developed and implemented a satellite playoff system for five counties, reducing travel costs and making district tournaments more cost-effective during a time of budgetary constraints.

Grasso’s career has been marked by recognition and honors that reflect his outstanding service to education-based athletics. He received the Principal of the Year Award from the PTSA County Council in 1998, was inducted into the St. Petersburg High School Hall of Fame in 2002, earned the Florida Athletic Coaches Association Distinguished Service Award in 2005, was inducted into the Clearwater High School Hall of Fame in 2016, and that same year was honored with the Florida Interscholastic Athletic Administrators Association Meritorious Award. In 2019 Pinellas County Schools established the “Nickolas Grasso Leadership” award which recognizes the Athletic Administrator that best demonstrates integrity, compassion, teamwork, fair-play and dedication to the job.

Through his roles as a coach, administrator, County Athletic Director, and executive leader, as well as his dedicated service on the FHSAA Board of Directors and within the local community, Nickolas Grasso has devoted his distinguished career to advancing and supporting coaches and student-athletes across the state of Florida.