Sarasota’s deputy county administrator steps down following stormwater issues

Key Information

• Resignation: Cunningham resigns from Sarasota County Government effective July 31.
• Background: Served 13 years; held the role of assistant county administrator since 2012.
• Investigation Findings: County neglected flood-control infrastructure and failed to address staffing shortages, contributing to severe flooding during the 2024 storm season.
• New Department: Sarasota County Commission approved a standalone stormwater department in response to public concerns.
• Career: Over 30 years of experience in government; previous roles in multiple Florida counties and Texas.
• Education: Holds a master’s degree in public administration and a bachelor’s degree in public policy analysis.

County officials did not disclose the reason for Cunningham’s resignation but said in an emailed statement that County Administrator Jonathan Lewis had accepted it.

“After 13 years of employment with Sarasota County Government, Cunningham will step down from his role on July 31,” the statement said. “County administration is reviewing the hiring process moving forward.”

Cunningham could not be reached for comment.

His departure, effective at the end of the month, follows mounting public scrutiny sparked by a joint investigation from the Florida Trident and Suncoast Searchlight, which found the county ignored repeated warnings, failed to maintain key flood-control infrastructure, and allowed critical staff vacancies to go unfilled — all contributing to catastrophic flooding during the 2024 storm season.

The investigation also uncovered that longstanding infrastructure like Phillippi Creek had been neglected for decades, essential flood protocols were disregarded or forgotten, and millions in stormwater assessment funds were left unused or diverted — despite clear recommendations from a county-funded consultant report intended to reform the system.

Cunningham, 60, was recently reassigned by Lewis to oversee stormwater operations alongside Public Works Director Spencer Anderson, who reports directly to Cunningham. Together, Cunningham and Anderson were the two top officials overseeing stormwater operations during the period when many of the failures occurred.

The resignation also comes just days after the Sarasota County Commission voted to create a standalone stormwater department that will report directly to the county administrator — part of a broader restructuring effort following public outcry. Ben Quartermaine, a former county stormwater engineering and operations manager, was hired to lead the new department and will start next month.

This isn’t the first time Cunningham considered leaving the county. He was a finalist for the Pasco County administrator job in 2017— an opportunity that arose around the same time Sarasota County announced it would hire then-North Port City Manager Jonathan Lewis to fill its top administrative post.

Cunningham has served as assistant county administrator since 2012 and brings more than 30 years of experience in city and county government.

Before coming to Sarasota, he held senior planning and development roles as executive director of planning and development in Denton, Texas; Polk County, Florida; and several counties in Maryland, as well as Jacksonville, North Carolina, according to his county biography.

A former U.S. Marine, Cunningham served eight years as a combat engineer, including deployments during Operations Desert Storm and Desert Shield, his bio says. He holds a master’s degree in public administration with a focus in urban management from the University of Baltimore and a bachelor’s degree in public policy analysis from Sojourner Douglass College.

The departure marks a significant moment in the county’s evolving stormwater response and follows months of resident frustration and calls for accountability focusing on Lewis and Anderson, but not Cunningham.

This story was produced by Suncoast Searchlight, a nonprofit newsroom of the Community News Collaborative serving Sarasota, Manatee, and DeSoto counties; and Florida Trident, a nonprofit newsroom of the Florida Center for Government Accountability. Learn more at suncoastsearchlight.org and floridatrident.org