Cassandra Jackson was at ease as she sat in a cherry wood-trimmed accent chair inside the living room of her grand Golden Eagle home, ready to talk. Her legal career with the city of Tallahassee will soon sunset. A new chapter awaits.
Yet, she never sought out to be the top legal counsel for the city of Tallahassee, let alone the first woman or first Black person to hold the position in the city’s 200-year history. All she ever wanted to be was “a great lawyer.”
The appointment was an honor, although she admits feeling the weight of being the first. It conjured stories of pain and prejudice. Like the time her father, a mechanic by trade, attempted to earn extra money at an apartment complex in Jacksonville through his lawn care business. He worked a one-day tryout from sunup to sundown. Despite being told he did a good job, he was rejected.
Another story involved her mother, who responded to a help wanted ad at a dry cleaners. She showed up for the interview and was told she “was too dark” to be seen out front interacting with customers. In a hurt voice, Jackson said this was the early 1960s. Jim Crow South.
Decades later, even with lived lessons from her own family’s history, Jackson said becoming the city attorney wasn’t just an accomplishment for her.
“I get this honor, and I’m just thinking ‘I am standing on the shoulders of my ancestors, and I’m showing what we can do,” Jackson said. “We can be professional if you just get the opportunity to do it.'”
In February 2018, Jackson was appointed as city attorney and she officially retires on June 1. In a rare interview with the Tallahassee Democrat, Jackson shares what drove her to practice law, particularly with the city of Tallahassee for nearly 21 years, and what ultimately made her leave.
Until now, Jackson has not openly talked about her reaction to text messages between a top city official and a developer’s attorney that disparaged her expertise on development matters or the dark cloud days of cooperating with the FBI during its years-long undercover probe into public corruption at City Hall.
Nor has she gone into great detail about the Florida Supreme Court’s landmark ruling that said Marsy’s Law can’t be used to categorically withhold the identity of police officers who use deadly force. Jackson’s legal team prevailed after arguing that “a few officers” led by the police union were transforming Marsy’s Law “into a cloak of anonymity for police conduct to the detriment of the public these officers serve.”
As she looks back on her stellar career, Jackson is proud of the work she’s done and what she brought to the legal table.
“I want to go out on a high note,” Jackson said. “I’m not saying I’ll never be a lawyer for a city again. I won’t be doing it in 2024 (as she plans to travel much of the year) … I loved helping people. I think that’s why I went into public service.”
Cassandra Jackson: ‘I wasn’t seeking, I was always found’
She grew up in Jacksonville and remembers when in elementary school the idea of practicing law began to shape who she wanted to be in life.
Jackson’s great-grand mother lived with her family. After school, young Jackson would find the matriarch watching the famed “Perry Mason,” show featuring a brilliant criminal defense attorney.
“He’s helping people,” Jackson recalled. “He’s getting stuff done. He figures out where’s the right way to go.”
It stuck. In 1984, Jackson received her bachelor’s degree in political science from Stetson University in Deland and her law degree two years later from her alma mater.
Most of her legal career has been spent in the public sector. She passed the Florida Bar in 1987 and, the same year, cut her teeth as an assistant city attorney for the city of St. Petersburg for three years.
As Jackson, 62, talked about her passion for the law, politics and people, a stack of inspirational and biographic books were at her side. Books like “The Most Important Thing I Know” featuring life lessons from Colin Powell, Stephen Covey and Maya Angelou and Michelle Obama’s “The Light We Carry” offer a glimpse into how she wanted to show up in the world and for her family.
The mother of three grown children will celebrate her 39th wedding anniversary this year with her husband, Jesse Jackson, a former school superintendent in Central Florida who also served as superintendent for the Florida State University School.
As her career progressed, Jackson focused on labor and employment law. In 1990, the Jacksons moved to Tallahassee when her son was 6 months old and she worked as a part-time hearing officer for the Public Employees Relations Commission, which specialized in labor union disputes.
From 1991 to 1996, she served as an assistant county attorney for the Leon County Board of County Commissioners. Jackson left the county when she gave birth to her second child and went to private practice for a short stint. By 1998, she was appointed by the late Gov. Lawton Chiles to serve as a commissioner at the Public Employees Relations Commission.
She spent much of the latter part of her career with the city of Tallahassee, with the exception of a year as the city of Lakeland’s assistant city attorney. In Tallahassee, she served as human resources manager, assistant city attorney, senior assistant city attorney and deputy city attorney before being named as the city’s top counsel.
“I wasn’t the person trying to get to know someone so that I could somehow get moved up. I just always did my best,” Jackson said. “And, I have to say, I was always found. I wasn’t seeking, I was always found.”
Marsy’s Law, a landmark moment for Jackson and Florida
For Jackson, the city of Tallahassee’s moment before the Florida Supreme Court was a career highlight.
The 2020 case involved two Tallahassee Police Department officers whose identities were shielded after a spate of police shootings that fueled local protests in the days after the death of George Floyd at the hands of a Minneapolis police officer.
In 2023, the Court ruled Marsy’s Law couldn’t be used to protect the identities of police officers who used deadly force — a decision that would impact police accountability across Florida and potentially influence others states.
The conservative high court, in a 6-0 decision, opined Marsy’s Law, an amendment to the state constitution approved by voters in 2018 that granted a number of rights to crime victims, doesn’t guarantee anonymity for police officers — or any victim of crime.
TPD, managed by the chief of police, and the city manager’s office were at odds about the disclosure of the officers’ names. Jackson led the charge in ensuring there wasn’t “a secret police force” in such cases — a move also supported by the Tallahassee Democrat and other media outlets.
“It is very rare that the press and government are on the same side,” Jackson said. “It was a milestone, right? We were seeing things the same way.
As I said, I majored in political science. I’m about the process. I believe the press has a role. The press needs to help us get information to the public and so, I was just like ‘This is fantastic.’ Quality lawyers on both sides, all sides. It was a great experience.”
FBI investigation at City Hall was uncharted territory for Jackson
When federal grand jury subpoenas dropped at City Hall in June 2017, it was like a bomb went off. Jackson, who was appointed a year later, was the city attorney through most of the federal probe as prosecutors interviewed city employees and potential witnesses.
The feds were investigating disgraced former mayor and commissioner Scott Maddox, his former longtime chief of staff and romantic partner Paige Carter-Smith and noted businessman J.T. Burnette in a bribery scheme that ultimately stained the city’s reputation.
It was Jackson’s first time interacting with the FBI. She said when she came on board, the relationship between the FBI and the city improved and the agency viewed itself and the city to be “on the same side.”
“That was very good for us, because that means we’re not the target. The office, the city, its executives,” said Jackson, adding the FBI at times called her directly for records. “I just said, ‘Hey, whatever you need, we are here to provide it.'”
She describes that period involving the FBI investigation as “a tremendous growth opportunity.”
“I got a chance to work in an area of criminal law … I don’t do criminal law,” Jackson said. “I wasn’t familiar with it, so I had to kind of bone up on it a little bit.
I think they just wanted to know that the city was good, and we’re not about doing wrong. And, I told them that … They just thanked me all the time for my cooperation … It was a great experience, not one I want to repeat.”
Jackson opens up about text messages, disappointment in city leaders’ silence
As city attorney, Jackson’s office dealt with an array of legal matters. Her background was rooted in labor and employment law, but she was proficient in other areas that included land use law.
Yet, some saw a series of text messages from Assistant City Manager Wayne Tedder’s city-issued phone to Gary Hunter, an attorney for Green Pointe Developers, as a direct attack on Jackson’s legal acumen.
Jackson said she was stunned to read the text exchange. Hunter’s Jacksonville-based client plans to build the largest master planned community in northeast Tallahassee in recent years at what’s being called “The Heel.”
A Planned Unit Development Agreement said the 900-acre development, located on Welaunee Plantation land, calls for the buildout of a new road that will cut across a portion of the Miccosukee Greenway, which alarmed cyclists and other greenway users.
In a text exchange, Tedder commiserates with the developer’s attorney and tells him it’s “pretty dang obvious the city attorney believes staff has given away the farm.”
“Unfortunately she lacks the credentials, knowledge and experience with the issues to make a positive contribution to this level of work,” Tedder writes in the text.
When asked if Tedder’s text exchange played a role in her decision to leave the city, Jackson said, “Oh, yes.”
She had no knowledge about the exchange until a public records request was made for them, adding the city attorney’s office reviews all record requests.
“My mouth fell open,” said Jackson, when she first read the comments. “Wayne Tedder was one of the most supportive people of me when I started as the city attorney.”
She said Tedder’s texts played a role but so did the lack of public response from the city manager’s office and the City Commission. She was disappointed to see little acknowledgment of the texts by the full commission, including the Power 3 of Mayor John Dailey and Commissioners Curtis Richardson and Dianne Williams-Cox.
City Manager Reese Goad said nothing publicly about the texts. Nor did most of the City Commission, outside of praising Jackson for her service and contributions. City Commissioner Jeremy Matlow, who first revealed the text messages, posted them on social media and blasted Tedder for what appear to be a far-too cozy relationship with a developer’s attorney. He maintained that a “toxic” and divisive culture at City Hall drove Jackson out.
When asked what she thought the response should have been, Jackson said, “I can’t say, but I do think there should have been one” from the city brass, along with accountability.
In an interview with the Democrat, Tedder said the text exchange was never about Jackson’s legal ability but rather about “a concurrency issue that was very, very technical.”
“We only have one individual in the entire organization who understands this stuff and does that part of the negotiation for us because it’s complicated,” said Tedder, referring to Keith Burnsed, assistant director of city’s Growth Management Department. “In fact … he’s recognized across the state as the leading concurrency specialist in the entire state of Florida.
That text was about concurrency. Never, ever ever was it about her abilities as an attorney. Never.”
Tedder said the “private conversation,” which is a public record under Florida’s Sunshine law, was never meant to become public and it become “politicized.”
“It’s sad to see her go because, like I said, we’ve had a great working relationship over the years,” Tedder said. “I only wish her the best. I don’t know what she has in mind in the future. But, this work is hard, and when it got as political as it did, for a lot of reasons, not related to she nor I, it’s hard work. This job is very hard when it gets in the political arena.”
Jackson said she never talked to Tedder again after she read the texts. She said he called her and left a message. She never responded.
Soon after the texts were made public, Jackson resigned effective Nov. 24 — more than a month ahead of when she planned to announce her retirement on Jan. 1, 2024. There was no resignation letter, only a contract amendment in which Jackson retained her full pay and benefits as she became a legal advisor to her retirement date.
Former peers say Jackson was well researched, committed and looked out for people
Former City Attorney Lew Shelley’s retirement from the city opened the door for Jackson to be named as his successor. He was pleased by the appointment and thought she was more than capable of taking the legal reigns.
Like many, he learned about the text controversy by reading the Democrat.
“I was very surprised that anybody in the city manager’s office would be talking about Cassandra not knowing anything about land use or development because that was just clearly not the case,” said Shelley, adding Jackson worked with the city management members on a number of developments in his five years as city attorney.
He leaned on her quite a bit in other areas as well — even matters in which he had expertise, like the contract negotiations process with the police union and with the firefighters.
“During that period of time that she was city attorney, I think she’s served the city, its elected officials and its managers greatly,” Shelley said, “Despite the obvious conflict between the five members of the commission.”
He’s referring to the often 3-2 voting dynamic at the City Commission that pits Dailey, Richardson and Williams-Cox against Matlow and Commissioner Jack Porter. At times, commissioners are seen bickering, bristling and talking over one another on the dais. Matlow, meanwhile, turns his grievances with his colleagues into often scathing social media posts.
Jackson herself noted the climate at City Hall “doesn’t seem to be getting better.” Yet, through it all, she maintained her commitment to serve the office and was seen as a “rock star” among other lawyers.
Rebecca O’Hare, deputy general counsel for the Florida League of Cities, said she admired Jackson. She wears many hats that include serving as an officer for the Florida Municipal Attorneys Association; Jackson served on its executive committee and helped craft educational seminar topics.
The statewide roles allowed her to see Jackson interact with professionals beyond the capital city and offer guidance on complicated issues. In addition, if O’Hare ever reached out to Jackson on a prickly issue, she knew she’d get a well researched response.
“She’s just been a great resource in that regard,” O’Hare said. “Nobody gets paid for doing any of this, and she did this, in addition to serving as the full-time city attorney for the city of Tallahassee, which is a total round-the-clock job.”
Hetal Desai, an administrative law judge for the Florida Division of Administrative Hearings, worked in the city attorney’s office in Tallahassee from 2005 to 2013. Desai got to know Jackson well and said she was the kind of person who didn’t just “off the cuff tell you something.”
“She would research it,” Desai said. “If she gives you an answer, you know that she’s looked into it.”
As for Jackson’s management style, Desai said, “she hires good people, and she trusts them. But, she also has an open door policy so you can always go and just talk about stuff with her.”
They’d go for walks at work. One memory of Jackson made Desai laugh, adding “this is how classy she was.” When Desai was pregnant with her first child, Jackson was already a working mother.
“I really didn’t know how to be a professional and be pregnant at the same time,” Desai said. “So one day, she came into my office and she gave me a box and said it was a gift for me. It was a maternity dress and she said, ‘Hetal, it’s time.'”
That was Jackson’s gentle way of saying Desai couldn’t keep wearing the typical lawyer suits she’d been accustomed to, adding “she was just very classy about how she would give me advice.”
Whether it was life experiences or her heart, Jackson understood people. She often approached her work the same way.
Back in her living room, Jackson shares stories of her childhood, her competitive streak and her pursuit of excellence as a high school valedictorian and college graduate with honors. She laughs a lot, showing her softer side. But, she was no-nonsense about how she wants people to view her legal legacy and her time at the city of Tallahassee.
As Jackson retires, she wants people to know she’ll be just fine.
“Sometimes I run into people and they go, ‘You left,” Jackson said. “I was like, ‘You know, it was just time to go.’
I really believe I gave my all, probably more — and I’m just going to say, I think more than any appointed official. I put in the time. I put in the stress. I put in the prayer to be the best I could be for the city.”
Contact Economic Development Reporter TaMaryn Waters at tlwaters@tallahassee.com and follow @TaMarynWaters on X.
This article originally appeared on Tallahassee Democrat: City Attorney Cassandra Jackson talks about retirement, texts, FBI
