Hillsborough County has fired its once-celebrated emergency management director after a lengthy internal investigation found problems with his leadership.
Timothy Dudley Jr., who saw Hillsborough through harrowing back-to-back hurricanes in 2024, was fired Tuesday, the county said. The Tampa Bay Times previously reported that he was placed on paid administrative leave in March.
Until now, the county had shared little information about Dudley’s removal.
Public records released to the Times on Tuesday show that what began as one employee complaint about denied leave time grew into a wide-ranging inquiry after Dudley appeared to interfere with a human resources review.
“Dudley’s actions reveal that he responded to complaints by his staff and the investigation of those complaints by deliberately moving out of the sunshine and into the shade,” Donna Smith, an attorney hired to review the county’s investigative work, wrote in an executive summary.
The investigation spanned nearly 10 months, consisted of interviews with 15 witnesses, and produced two human resources reports and an external review totaling more than 100 pages. The documents chronicle how a once-acclaimed leader created an unstable working environment in which employees say they feared retribution.
Dudley, who had a salary of $152,484.80, did not return multiple phone calls, emails or messages seeking comment for this story.
In a statement to the Times, the county said it would not provide additional details beyond the public documents on the investigation, calling the situation a “personnel matter.”
“The County remains focused on serving the public and maintaining the highest professional standards across all of our departments,” the statement said. Fire Rescue Chief Jason Dougherty has been serving as emergency management director in the interim.
It started with a time-off request
In June 2025, Erik Challenger filed a complaint with the human resources department about a time-off request that was denied during that year’s hurricane season. Although the human resources investigation found Challenger’s request wasn’t mishandled, it uncovered a pattern of behavior from Dudley that investigators say amounted to interference.
The county placed the director on paid administrative leave March 13.
Employees described Dudley as threatening and dismissive, according to the records. Investigators found that between January 2020 and April 2025, at least 21 employees resigned in the emergency management office — among them, emergency management coordinators and section chiefs. At any one time, the department has about 20 employees, according to the records.
“The volume and concentration of departures, particularly among employees hired during Dudley’s tenure as division chief, and within one-two years of employment, is notable,” Smith wrote.
Additionally, she noted, the churn supported witness testimony that former employees felt targeted, micromanaged and unable to work under the department’s leadership.
Dudley denied several claims raised by employees, including that staff feared speaking up.
Regarding employee turnover, he said he inherited a department in “intense organizational transition” that included a pandemic, civil unrest and multiple hurricanes. Dudley took over in 2019.
“Any stress staff experienced stemmed largely from this transition, not from intentional hostility on my part,” Dudley told investigators, according to the report. “I did not create or intend to create a hostile environment.”
One employee acknowledged years of instability within the department dating to Hurricane Irma in 2017. However, the employee said Dudley led with a strict, top-down and militaristic style that rubbed some people the wrong way.
Months before Dudley was removed, the records show, tensions boiled over.
In September, Yulissa Dale-McClain, a program coordinator in emergency management, said during a training that employees were “f—ing ungrateful” and that staff were “mistreating” Dudley. She said she wanted the probe to “hurry up.”
The investigation found that Dudley then failed to properly reprimand Dale-McClain for those comments.
In another instance, an employee felt uneasy after a one-on-one with the director. The employee told human resources that Dudley made remarks about sitting back and watching “how everything’s gonna fail.”
“We are a team, and if one of us fails, we all fail — we’re dealing with people’s lives,” the employee told another staff member, according to the report.
Challenger, who filed the initial complaint about time off, sued Hillsborough’s Board of County Commissioners in federal court over the matter in March. He didn’t have an attorney and filed the complaint himself.
Court records show the county agreed to settle the case last month. Hillsborough County did not respond to questions regarding the settlement.
Both Challenger and Dale-McClain, who are still Hillsborough employees, declined to comment through a county spokesperson.
Dudley’s tenure started strong
Hillsborough County hired Dudley after he spent five years in Pinellas County as a senior emergency management coordinator, according to his personnel file. The file showed glowing reviews early in his tenure.
Last year, Dudley received the Bill Horne Outstanding Public Administrator Award from the American Society for Public Administration.
Under Dudley’s guidance, the county “navigated one of the most challenging hurricane seasons in recent memory,” Hillsborough County Fire Rescue wrote on Facebook after he received the award.
An emergency director is in charge of setting priorities so residents are prepared ahead of a disaster, like a hurricane.
They guide people’s decision-making, David Merrick, the director of the Emergency Management and Homeland Security Program at Florida State University, previously told the Times.
Commissioner Chris Boles told the Times on Wednesday that there will be no interruption to services as the county approaches peak hurricane season this year.
He and the county expressed confidence in Dougherty, who has been serving as the interim emergency management director since the spring. Dougherty was recently named Florida’s Fire Chief of the Year, according to a Hillsborough news release.
Local governments often have their fire rescue chiefs also serve as emergency managers, Merrick previously told the Times. A greater workload, he said, should be “doable.”
“Because in theory, it’s going to be for a relatively short period,” Merrick said.
The county has not responded to questions about plans to fill the job on a permanent basis.
Times staff writer Lizzy Alspach contributed to this report.
We want to hear from you: If you have more information about Hillsborough’s emergency management department we should consider, please contact Michaela Mulligan at mmulligan@tampabay.com or Bethany Barnes at bbarnes@tampabay.com. Information can be shared confidentially. Michaela can also be reached securely via Signal at: MMulligan97. Bethany can also be reached securely via Signal at: Betsbarnes.77
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