Floridian of the Year
The Advocate: Yolanda Cash Jackson
Attorney and lobbyist Yolanda Cash Jackson has built a career forging paths of opportunity for others.
The first time Yolanda Cash Jackson saw the sculpture of Mary McLeod Bethune was in 2021 in Pietrasanta, a small town along the Tuscan coast where master sculptor Nilda Comas had carved the three-ton figure out of marble from the same quarry Michelangelo used to create David and other masterpieces. Bethune is known as the “First Lady of the Struggle” for her efforts to pave the way for Blacks in education and civil rights; the towering stone figure depicts Bethune in academic regalia adorned with a simple pearl necklace and holding a single black rose.
Jackson — a South Florida attorney and lobbyist who grew up in Liberty City and followed an uphill journey to become one of the state’s leading legal and legislative advocates — made the trip to Italy with a group of fundraisers who had commissioned the statue, including several of her fellow Delta Sigma Theta sorority sisters. Moved at the sight, the women began recounting how Bethune’s legacy of lifting others had endured and changed so many lives, including their own. Bethune had called the students at her school, which became Bethune- Cookman University in Daytona Beach, her “black roses.” More than 60 years after her death, generations of roses followed and were in full bloom.
A year later in July, Jackson was in the U.S. Capitol for the dedication of the statue. Jackson played a pivotal role in securing Bethune as one of two figures representing Florida (refrigeration and air conditioning inventor Dr. John Gorrie is the other) in one of the nation’s most hallowed spaces. As the chamber filled with dignitaries and the voices of a choir reverberated in the cavernous space, seeing the likeness of Bethune left Jackson in awe again. “This is the place where we almost lost our democracy,” Jackson says, recalling the Jan. 6 insurrection. “Here we have this Black woman with a dollar and 50 cents (the sum paid for the land where Bethune started her school), a dream and a bunch of Black kids she called black roses coming up in here. It was an amazing, amazing display of democracy.”
Florida is the first state to have an African- American person represent it in the national collection. But it’s an achievement that likely would not have happened but for Jackson’s ability to build consensus. The push to place Bethune in the hall began in 2016 amid a backlash against Confederate symbols following the slayings of nine worshippers at a historic Black church in Charleston, S.C. Then Florida Gov. Rick Scott signed a bill removing the statue of Confederate Gen. Edmund Kirby Smith, but elevating another historic figure would be delicate work. Jackson, a lobbyist for Bethune-Cookman University, championed a bill by Sen. Perry Thurston and Rep. Patrick Henry. It passed unanimously in 2018.
Jackson is quick to say credit is owed to many, including Daisy Grimes, a Bethune- Cookman alumna and retiree who gathered petition signatures; students who rallied for the change; lawmakers and two governors who gave their approval; and Nancy Lohman, the Ormond Beach businesswoman and philanthropist who led the fundraising.
But the project speaks to Jackson’s achievements in forging paths of opportunity for others, say colleagues and friends, representing historically Black colleges and universities; chairing the Miami-Dade Beacon Council, a public-private economic development partnership; and funding a law school scholarship at the University of Florida.
“Lobbying is about relationships, and nobody makes better relationships than Yolanda because of her personality and her gift of preparedness,” says John Thrasher, the former Florida House Speaker, state senator and retired president of Florida State University. “She knows how to work the process. She knows how to win, and she knows how to modify it when maybe she’s not going to win, and that’s what makes a good lobbyist. Somebody who’ll come in and tell you the truth, tell you both sides of it, but be a strong advocate for what she believes in. She does that so successfully.”
From Liberty City to the Law
Jackson grew up in a close-knit family with Bahamian roots. Thanksgiving dinners included a typical spread of turkey, collard greens, conch dressing and guava duff. “That whole Bahamian influence growing up certainly is the foundation for a lot of my beliefs and passions,” Jackson says.
Education was paramount in the Cash household — Jackson’s mother was a guidance counselor and her father was a school principal and later a pastor. Community involvement was a given. “My parents were active in the church, in civic stuff. They volunteered,” says Jackson, who participated in the Girl Scouts. “We grew up in service. Service is the price you pay for the space you occupy. That was our philosophy.”
Jackson excelled in school, serving as editor of her high school newspaper and graduating from Miami’s Edison High School with honors. While both of her parents had attended historically Black colleges, Jackson headed to Gainesville to study journalism at the University of Florida.
She ended up majoring in public relations, minoring in marketing and landing a job after graduating in 1980 at Sears, then the largest retail store in the country. “It was prestigious, and they had benefits. It was a great job,” Jackson says.
But the honeymoon didn’t last. “I got passed over for a promotion” to a managerial position, she says, which went instead to a white man without a college degree. It was “devastating,” she says, and the experience motivated her to apply to law school. “Never again would I ever be dependent on letting someone else determine my outcome. As a lawyer, you don’t like the law, you change it, and if there’s an injustice, you change it. You fight,” she says.
At age 29, she was the oldest student in her law class at the University of Florida, but she was “laser-focused” on her school work. Her husband, Fernando Jackson, a former football player at UF and on the U.S. Football League’s Jacksonville Bulls, took on two jobs, including driving a truck, to help put her through school as he finished his own undergraduate degree. Jackson continued to work at Sears for a time, selling washers and dryers on commission, but later took a job working in the law office of Kathleen Fox, a family law attorney in Gainesville.
After graduating in 1989, she landed a clerkship in the Miami office of Shutts & Bowen, a law firm that has worked with Florida businesses since the days of Henry Flagler.
She was making more than her parents ever had in their careers — “they paid me $1,000 a week,” she says. She was the firm’s first Black woman lawyer. “It was surreal to leave Liberty City every morning and go downtown to a place where they’d never had a Black woman (working as a lawyer) before,” she recalls. The clerkship turned into a job offer, and she spent the next 3½ years at Shutts & Bowen followed by a brief stint at a firm started by some former colleagues.
A lobbyist is born
In late 1994, Jackson’s father died. Then her husband, Fernando, died unexpectedly 12 days later. The tragedies might have broken her had it not been for her abiding faith. “I always know at the end of the day, he is going to make a way out,” she says.
She ended up moving to another law firm but found little joy in the litigation work she was doing. A colleague noticed and encouraged Jackson, who was then 41, to follow her heart and find her passion. “It gave me courage,” she recalls. “My husband had passed; my dad had passed. I’m not a big risk taker. I’m not the one jumping out of a plane, but at that moment I did. I wanted to start a lobbying practice.”
The firm she was working for at the time, she says, wasn’t much interested in lobbying so Jackson threw herself into campaign politics, working first as a researcher on legal challenges to the state’s 1992 redistricting efforts, which gave rise to minority-access districts. She held fundraisers for Carrie Meek, a Miami Democrat who in 1992 became the first Black woman elected to Congress from Florida, and the two developed a friendship that lasted until Meek’s death in 2021. Jackson went on to co-chair NAACP voter registration drives with Meek’s son, Kendrick, and ran his 1998 campaign for the state Senate.
Jackson’s break into lobbying happened a year later. “I was the one who hired her, with Alan Becker,” says Bernie Friedman, who runs Becker & Poliakoff’s lobbying practice. Her aversion to litigation made sense to Friedman. “We knew that she had tremendous potential in lobbying because she was such a people person. She had real vision and sort of an agenda of what she wanted to do and who she wanted to help,” Friedman recalls. “We just had to teach her how to make money.”
Jackson landed her first client in January 1999 ahead of the regular legislative session in Tallahassee. A lobbyist for Golden Rule Insurance asked her if she knew how they could get a meeting with then state-Rep. Betty Holzendorf, who was vice chair of the banking and insurance committee. Jackson told the Golden Rule lobbyist that she could arrange for the lobbyist to meet Holzendorf. Golden Rule hired Jackson for $5,000 a month, and she remained the health care insurer’s Florida lobbyist until it was bought by UnitedHealthcare in 2003.
Today, Friedman says, Jackson is one of the firm’s biggest rainmakers, with a roster of about three dozen clients, ranging from historically Black colleges and universities to municipalities to trade associations and corporations, including AT&T, TECO Energy and Sunshine Health. He attributes her success to the good she does for the community and her connections. “She knows so many people and is so well networked. People gravitate to her, and they trust her,” Friedman says.
One client, Lanetta Bronté-Hall, president and chief health officer of the Foundation for Sickle Cell Disease Research in Hollywood, met Jackson through a patient, and the two quickly bonded. “You could just feel her warmth and tell that she really wanted to help. She had a relative with sickle cell disease and didn’t really understand a lot about what he was going through,” but she wanted to learn, Bronté-Hall says.
As Bronté-Hall taught Jackson about sickle cell disease, Jackson coached her on how the legislative process worked and helped her prepare a “one-pager” they could present to lawmakers to make a case for funding to expand the organization’s clinic sites, where patients can get infusions, participate in clinical research and receive other supportive care. Then they hit the halls of the Capitol. “One thing that she always told me is, ‘Listen, we’re not playing in the kiddie pool.’ So she has helped me get out of the kiddie pool and has been very instrumental in getting me in front of legislators to present the foundation,” Bronté-Hall says.
Jackson also used her connections to get lawmakers into the foundation’s clinics, where they could see firsthand what patients with sickle cell disease go through and how the organization is helping — and that exposure had an impact. State lawmakers included a $3-million appropriation for the organization in their 2022 funding bill that enabled the group to open several treatment locations around the state.
Guiding clients like Bronté-Hall through the legislative process is Jackson’s specialty, and those who’ve worked with her say her vision, determination and grit have made her one of the most effective lobbyists in the state. Her knack for working both sides of the aisle and getting along with just about anyone — “you find commonalities,” Jackson says — has enabled her to build coalitions and alliances on issues that bridge ideological divides. And her inclination to stay the course and “not sweat the setbacks” has also served her well in the legislative arena, where change is not always sweeping and sudden, but often tedious and incremental.
In 2016, the year that Florida voters approved a constitutional amendment expanding the legal use of medical cannabis, Jackson lobbied pro bono to help Black farmers gain entry into the burgeoning industry.
At the time, the requirements for obtaining a license, Jackson says, made it nearly impossible for most Black farmers to participate in the process. Only those nurseries that had been in business for 30 years or longer and produced at least 400,000 plants on an annual basis were allowed to apply, and the application cost was $60,000. Amid her efforts, in 2017 the Legislature set aside one medical marijuana license for a Black farmer with ties to Florida.
Five years later, the fruits of that labor are finally coming into focus. In September, the state Department of Health issued a “written notice of intent” for the approval of a medical-marijuana operating license to Terry Donnell Gwinn, a Black farmer in Suwannee County who has operated the Gwinn Brothers Farm for more than four decades. As Jackson sees it, it’s just another example of the chasm between the haves and have-nots and the slow grind of the process. “The have-nots have been waiting for a while,” she says.
Jackson’s biggest impact, arguably, comes from the work she’s done advocating for state financial support for the state’s three private historically Black colleges and universities: Bethune-Cookman University in Daytona Beach, Florida Memorial University in Miami Gardens and Edward Waters University in Jacksonville.
In 2018, while Mary McLeod Bethune’s statue was being planned, her namesake school in Daytona Beach was teetering on the verge of financial collapse that then-interim President Hubert Grimes described at the time as an “existential threat” to the university. Jackson worked closely in 2020 with members of the Black caucus and Gov. Ron DeSantis to secure $16.96 million (a $13 million increase) in funding that saved Bethune- Cookman, and along with it, Bethune’s legacy. Edward Waters College and Florida Memorial University landed $6.4 million and $7 million, respectively, an increase of $3.5 million each. In the years since, there have been no cuts.
A. Zachary Faison, president of Edward Waters University, says that money has provided critical “gap funding” for students to make up the difference between the cost of attendance and the federal aid that they receive — which is key to retention. It has also enabled his university to launch a master’s of business in administration program, which made the school’s transition from being a college to a university possible.
“It’s been a great year of transition for us as a university,” he says, and it all started with Jackson. “Without that allocation from the state, the $3.5 million led by Yolanda Cash Jackson, all of those programs could not have happened. She truly is a trailblazer, and she has forever positively impacted Edward Waters University.”
Jackson says the state has gotten its return on investment in the institutions. In an era when college enrollment of men is declining, she notes that Black men are the largest demographic group of students enrolled at Edward Waters (42.7%). “What the state invested, they’ve gotten back in keeping these schools open and increasing the enrollment of a very important segment in our state,” she says.
Jackson is hopeful that the same strategies she’s relied on to help Florida’s HBCUs can help the minority communities she represents in South and Central Florida address their infrastructure needs so they can replace aging water pipes and tackle street flooding. Historically, those communities haven’t had the resources or the influence in Tallahassee to address those sort of challenges “and have just been neglected,” Jackson says. “I’m trying to get them to coalesce. Just like we’ve created this coalition with the HBCUs, I believe we can create a coalition of urban communities,” she says.
The principal’s daughter from Liberty City says she’s an educator at heart. “A lot of what I do is teach. Teach people who’ve never advocated for themselves how to advocate,” Jackson says. “Taking that passion and putting some process to it. One of the things I teach my clients is we’ve got to be selling what they’re buying.”
- Quarterbacked a state lobbying effort to replace a Confederate general’s statue representing Florida in the U.S. Capitol with one of civil rights pioneer Mary McLeod Bethune.
- Persuaded state lawmakers to reserve a medical marijuana business license for at least one Black farmer.
- Secured record amounts of state funding three years in a row (2020, 2021 and 2022) for Florida’s three private historically Black colleges and universities.
- Spearheaded the creation of the HBCU Pathway to Law Endowed Scholarship fund at the University of Florida’s Fredric G. Levin College of Law (endowed with gifts totaling more than $1.1 million) that provides scholarships to at least five graduates of historically Black colleges and universities who enroll at UF’s law school each year.
- Co-founded the National Black Professional Lobbyists Association with Alabama lobbyist Gregory Jones and government and external affairs consultant John A. Heath. The group, which convened its inaugural conference in October, aims to grow the ranks of African-American lobbyists and Black-owned government affairs firms across the nation. “We need to have other Black lobbyists in the pipeline,” Jackson says.
- This fall, became chair of the Miami-Dade Beacon Council, the county’s official economic development organization, and serves as an at-large member of Enterprise Florida.
From One Pioneer to Another
Former state Sen. Arthenia Joyner, who was the fifth Black woman lawyer and is the longest practicing Black woman lawyer in Florida history, calls Jackson a “pioneer” in Tallahassee’s lobbying arena. “She would tell you right away that she’s standing on the shoulders of women who blazed a trail either in lobbying, in law, in the Legislature itself, but she stands out because hers has been long-lived — years of hard work, outstanding work in the Legislature — and her reach has just been cultivated over the years. Her knowledge of the system is unparalleled.”