Years ago, someone told me something about leadership that has stuck with me:
Wisdom comes from experience. And experience often comes from making bad decisions.
After decades of working with CEOs, I believe that.
About 15 years ago, I worked with the CEO of a successful local company he had taken over from his father. He had grown up around the business. He knew the customers. He knew the employees. He had watched his father lead it.
And he was pretty confident he knew what he was doing.
Maybe a little too confident.
Several people began warning him about an employee he trusted completely. There were red flags. People tried to tell him. I tried to tell him.
He wouldn’t listen.
Then one day, his CFO walked into his office with evidence that could no longer be ignored. Fraud involving that trusted employee had cost the company nearly $1 million.
Suddenly, all those warnings looked very different.
The employee was fired. The CEO had to repair relationships with financial institutions and clean up a terrible mess.
But something else happened.
He learned.
That painful experience made him a wiser leader because he finally understood something every good leader eventually learns:
The people warning you aren’t always your enemies. Sometimes they’re the people trying to save you.
Which brings me to Mayor Donna Deegan and JTA.
More than a year ago, I had an opportunity to sit down with Mayor Deegan.
During our conversation, I told her I believed she had a blind spot regarding JTA and Nat Ford. News organizations were already raising serious questions about the authority.
She smiled and told me she trusted Nat.
I remember telling her something else very specifically:
JTA could become your JEA if you don’t start digging into this.
That is my personal recollection of our conversation.
At the time, nothing seemed to change.
But there were plenty of warning signs available publicly.
Beginning in 2023, Action News Jax investigator Emily Turner spent months examining JTA and reporting on executive compensation and travel, CEO Nat Ford’s time away from the office, declining services and other spending and management questions.
Then came Megan Hayward.
While serving on the JTA board, Hayward publicly questioned discrepancies in ridership figures, sponsorship spending and taxpayer-funded educational benefits for executives. In February 2025, Mayor Deegan filed legislation to replace Hayward before her term was finished.
Hayward believes her questioning of JTA contributed to her removal. The mayor’s office disputes that and has said Deegan selected former Neptune Beach Mayor Elaine Brown because of Brown’s transportation experience and because the change coincided with onboarding other board members.
Fair enough. Both sides should be heard.
But here’s the problem.
The warnings didn’t go away.
Today JTA is dealing with a major financial crisis, layoffs affecting nearly 200 positions and reductions or suspensions of transit services. The Florida Attorney General’s Office has also subpoenaed JTA records involving former CEO Nat Ford, his wife, contracts, tuition reimbursement, scholarships and other matters.
A subpoena is not proof that wrongdoing occurred.
But it certainly means there are questions serious enough to investigate.
And now the mayor’s office has said something I simply cannot get past.
Regarding JTA’s financial condition, the administration said the JTA board “was not previously aware of the dire nature of the agency’s financial situation. We became aware as they did.”
Maybe they didn’t know precisely how bad the final numbers were.
But they cannot reasonably say there weren’t warning signs.
Journalists were reporting them.
Board members were questioning them.
City Council members were raising them.
And according to Megan Hayward, she personally took concerns to the mayor. Deegan has acknowledged meeting with Hayward, although the two women disagree about what was discussed and how seriously those concerns were presented.
This is where the leadership lesson comes in.
The worst thing a leader can do when the red flags finally turn into a crisis is spend all their energy explaining why they didn’t know.
Sometimes the strongest words a leader can say are:
“We should have listened.”
Imagine how differently this would feel if Jacksonville heard something like:
We are disappointed by what has happened at JTA. There were people raising concerns earlier, and we should have paid closer attention. We are going to find out what happened, cooperate fully with the investigations, protect taxpayers and make sure the lessons from this are not repeated.
That’s leadership.
Not because it admits guilt for something the mayor may not have personally done.
But because leadership means accepting responsibility for what happens on your watch, learning from it and changing course when the facts tell you to.
And Jacksonville desperately needs that right now.
People are exhausted by government controversies involving huge amounts of taxpayer money.
They want answers. They want accountability. They want to know where their money went.
And if money was improperly spent, they want every legal avenue explored to recover it.
Most importantly, they want leaders who can say:
I missed something. I learned something. And I will do better.
That’s not weakness.
In my experience working with CEOs, that’s usually the moment a leader begins getting wiser.
And finally, a word to the people who kept asking uncomfortable questions.
Emily Turner kept digging. Megan Hayward kept asking questions from inside the JTA boardroom. And here at Eye on Jacksonville, Lindsey Roberts spent considerable time researching and writing about JTA, following the money, the decisions and the warning signs that deserved public attention.
They weren’t creating the problem by asking questions. They were trying to expose a problem before it became an even bigger one.
Investigative journalists, citizen journalists and board members willing to challenge management aren’t nuisances to good government. They are part of the guardrails that can keep an organization from driving straight over the cliff.
So to Lindsey, Emily, Megan and the others who spoke up when it would have been much easier to stay quiet:
You did your job. You asked the questions. You raised the red flags. And you deserved to be listened to.
Sometimes leadership isn’t being the person with all the answers.
Sometimes it’s being wise enough to listen to the people sounding the alarm.
