In 1999 Winn joined Governor Jeb Bush as his Education Policy Coordinator. While in that position, he was responsible for drafting and directing the Governor's education budget recommendations and legislative initiatives for all education sectors. These included the A+ Plan for Education, One Florida programs, K20 education system, and charter district legislation. He was also instrumental in crafting the John McKay Scholarship authorizing legislation. While in this position, he played a major role in developing the concept and implementation of measuring annual student learning gains, school grading formula, and the K20 data warehouse. Winn returned to the Department of Education with Commissioner Jim Horne to assist in the restructuring of the Department of Education and the K-20 education system. There he coordinated the massive restructuring of the Florida School Code, centralized all data and accountability operations, and participated in creating a high performing senior staff team. During his tenure as Commissioner, student achievement in reading and mathematics reached an all-time high. The achievement gap closed considerably and students with disabilities and limited English proficiency more than doubled their reading improvement. Also, Florida led the nation in the percentage of high school graduates taking at least one Advanced Placement exam. John Winn has built a solid reputation as an authority in statewide implementation of innovative education improvements and on policy issues facing public education at every level. He is respected throughout the Florida education community and nationally. Throughout his career, he has demonstrated commitment and compassion in improving education quality for all students.