Among these DROP participants, a dedicated subset of 183 employees were not satisfied with a standard 5-year pension bonus and opted instead for an expanded 8-year timeline. This 8-year subset alone accounts for $40,636,955 in total cash payouts—creating an additional $13,972,466 in extended windfall payouts above the standard 5-year timeline. Top administrative payouts are led by Chief Strategy Officer Jennifer Cupid-McCoy, who is set to collect a single pension cash bonus of over $1 milllion, $1,011,004 on top of her $200,720 annual salary and $44,872.57 in banked unused vacation, etc. hours. Cupid-McCoy’s estimated annual pension will be $97,561.  See the full list of Lee County School Pension Cash bonuses at: https://tripledippers.org/

“It is a shameful for the Lee County School Board to fire 275 classroom teachers and raid $45.4 million from our capital infrastructure accounts while protecting $250 million in pension bonuses for administrative elites. Taxpayers are forced to pay a mandatory 22.02% FRS surcharge—totaling over $8.8 million every year on these pension bonus employee salaries—while these ‘Triple Dippers’ pay zero percent into the retirement system.”  https://www.youtube.com/watch?v=o17qoClsjUA&start=7  and https://www.wgcu.org/education/2026-05-20/275-teachers-laid-off-lee-county-schools
– Dave Jaye, Chairman, Lee County Taxpayers Association; Lead Researcher, TripleDippers.org

While school districts like Collier and Duval County saved millions by privatizing janitorial services as far back as 2008, and public, private, and religious school systems routinely contract out non-instructional services, Lee County Schools refuses to streamline its non-educational operations. The district currently subsidizes 566 retired personnel drawing full paychecks and monthly pensions simultaneously, including non-instructional positions across Janitorial, Food Services, Transportation, Drivers Education, IT, and Clerical services.

“Collier County, Duval County, and other private and religious schools have successfully privatized janitorial, food services, transportation, and IT to keep dollars inside the classroom. Yet Lee County keeps hundreds of retired bureaucrats on payroll, paying out over $11.7 million in banked unused leave hours and absorbing full benefit surcharges instead of modernizing services.”

— Dave Jaye, Chairman, Lee County Taxpayers Association; Lead Researcher, TripleDippers.org

Alarmingly, these multi-million-dollar administrative payouts coincide with dismal academic outcomes for local students.

“The longer students spend in Lee County, the lower their test scores become. U.S. News & World Report documents https://www.usnews.com/education/k12/florida/districts/lee-103042 that 67% of Lee High School students fail basic math and 57% fail at basic reading, making these students not job-ready. Yet the Lee County School Board brags about an 89.8% graduation rate achieved through social promotion, not basic academic student achievement.”

— Dave Jaye, Chairman, Lee County Taxpayers Association; Lead Researcher, TripleDippers.org

FORT MYERS, FL — Facing a severe $92.4 Million operational deficit that has led to non-renewal notices for 457 teachers, assistant principals, and student support staff, the School District of Lee County continues to protect massive payouts for administrative elites. Fresh analysis of updated April 2026 public records reveals that the Lee County School Board has approved 566 active pension bonuses (DROP) total, carrying a staggering total liability of $250,493,912. Rather than cutting bureaucratic overhead or outsourcing non-instructional operations, the board has approved transferring $45.4 million out of the capital new building and infrastructure fund directly into operational accounts to cover its daily operating budget shortfalls.

This massive fiscal strain comes as traditional public schools in Lee County lost 1,946 non-charter students between the 2024–2025 and 2025–2026 school years—the operational equivalent of closing two full 1,000-student schools. Despite shrinking enrollment, the district continues to over-allocate funds to administrative payouts rather than rightsizing overhead.

Among these DROP participants, a dedicated subset of 183 employees were not satisfied with a standard 5-year pension bonus and opted instead for an expanded 8-year timeline. This 8-year subset alone accounts for $40,636,955 in total cash payouts—creating an additional $13,972,466 in extended windfall payouts above the standard 5-year timeline. Top administrative payouts are led by Chief Strategy Officer Jennifer Cupid-McCoy, who is set to collect a single pension cash bonus of over $1 milllion, $1,011,004 on top of her $200,720 annual salary and $44,872.57 in banked unused vacation, etc. hours. Cupid-McCoy’s estimated annual pension will be $97,561.  See the full list of Lee County School Pension Cash bonuses at: https://tripledippers.org/

Contact: Dave Jaye, Researcher | 586-488-5177 | dave.jaye55@gmail.com