Gary Brady

Cahn Fellow 2019

Principal, Hillsborough High School

Tampa, Florida

Gary Brady started his career in 1995, as an English and Reading teacher at Plant City High School in Hillsborough County, Florida. In 2009, he became an Assistant Principal at Strawberry Crest High School. In 2012, he became Assistant Principal for Curriculum and later, Assistant Principal for IB/Magnet Curriculum at Robinson High School. While at Robinson, the school earned its first "A" grade in school history and did so for the next four years. In addition, while the AP for Magnet/IB Curriculum, the IB Program earned a 100% IB Diploma Rate and was the only high school in the state of Florida to do so. Mr. Brady was appointed principal at Hillsborough High School in 2015. The school is designated as Title I and has over a 75% Free and Reduced Lunch population. After three years, Hillsborough improved by 69 points, to 550, earning a "B" grade from the State of Florida.

In June of 2022, Gary has received a promotion to the new role of Regional Superintendent. Instead of the positions in the district being divided by area, they are now divided by level, so Brady’s role involves checking on and visiting high schools and helping out the principals in throughout Hillsborough County.

In August of 2020, Brady was named Journalism Education Association’s 2020 Administrator of the Year.