When it comes to defending causes, Hugh Culverhouse Jr. has made it his pastime

Hugh Culverhouse Jr. was a young, feisty, chip-on-his-shoulder prosecutor with the U.S. Attorney's office in Miami in the late 1970s when the FBI came to him with a problem: Brigade 2506, a group of Cuban exiles against Fidel Castro, had put out a hit on his life. 

The FBI told Culverhouse the threats were credible, targeting him and an eyewitness to a car-bombing. They gave him two options: Buy a new car, to throw off the would-be assassins. Or buy a gun. 

“I said ‘I have a 1973 Beetle, and the only option was a 1969 AM radio,’” Culverhouse recalls, and even though he would go on to become a multimillionaire, money back then was tight. A proud native son of Alabama, Culverhouse then told the Feds that “my mom taught me to shoot when I was 6 years old.”   

He chose the gun. 

Culverhouse, fortunately, never had to use the weapon in a gunfight. 

Yet that story is an illustrative moment for his life and career. A part-time Sarasota resident since 1997, with a home in Oyster Bay Estates, and the developer behind one of the largest master-planned communities in the region, Palmer Ranch, Culverhouse, with his words and his wallet, has fought full-time constantly and consistently against what he considers multiple wrongdoings impacting a variety of people and communities across Sarasota, Longboat and Siesta Key. 

And it’s a fat wallet: Culverhouse, 75, has given away nearly his age in money, surpassing $73 million. 

Sometimes these are low-six figure donations to save Sarasota programs facing government shortfalls or government decisions he thinks, at best, are reckless and misguided. Sometimes it’s mid-six-figure campaign contributions to political candidates; mostly, but not always, Republicans, such as Donald Trump and Florida Gov. Ron DeSantis. Other times he’s taken out full-page advertisements in the Wall Street Journal to combat what he thinks is apathy on a national issue. And sometimes it’s as simple as donating wine for charity, or Japanese art, to his local religious organization, Church of the Redeemer in downtown Sarasota. 

“I don’t own a boat, and I don’t own a plane,” he says. “Helping people is my boat and plane.”

Diverse causes

Culverhouse, who also has a home in Coral Gables, outside Miami, isn’t afraid to court controversy, with his donations or the words he uses to sometimes back up his money. “I’ve had a lot of lawsuits, bumps and bruises along the way,” Culverhouse admits with a wink as he sits in his Palmer Ranch office, sipping a bottle of sparkling water. 

The wide variety of causes Culverhouse takes on, at first glance, seem contradictory. 

Photo by Lori Sax

One example: In June, Culverhouse, according to federal elections records, gave $500,000 to the Trump 47 Committee to elect former President Donald Trump. Culverhouse calls the donation a protest against what he considered a politically motivated case in the former president’s hush-money trial and conviction. Less than two months later, Culverhouse, along with his wife, Eliza, donated $107,643 to the local nonprofit Embracing Our Differences, for its annual large-scale art exhibition at Bayfront Park, which promotes inclusion, respect and kindness. The Culverhouse gift covered a highly publicized loss of state and county grants and, while Embracing our Differences is, in theory, a non-partisan organization, it’s safe to say the chances of a MAGA rally breaking out at one of its initiatives are zero.    

While Culverhouse’s “what” can be a paradox, his “why,” based on interviews with him and several in the Sarasota area who know him well, is much simpler: He detests bullies.  

“The media portray him as a hothead and bombastic,” says Rev. Charleston Wilson, the rector of the Church of the Redeemer. “The real Hugh is very truthful, nurturing, wise and winsome, and someone who is desperately trying to bring this community together.” 

Wilson, who in addition to the church shares a deep connection with Culverhouse as both are Alabama natives, confirms the anti-bully narrative. “He is passionate about underdogs,” Wilson says. “If he sees you doing something unfair, he will fight you with every dollar in his wallet.”

Florida state Sen. Joe Gruters — Culverhouse is one of his biggest contributors — says he doesn’t believe Culverhouse seeks out controversy, but his blunt approach can lead him there. “He wants to be part of the solution to big issues,” Gruters says. “There are a lot of people who talk. There are few people who talk and execute like Hugh does.”

Resilience and redemption

Like some other things in Culverhouse’s life, what seems glamorous on the surface has a more disruptive backstory. That starts with his father, Hugh Culverhouse Sr. 

Widely known in the area for owning the Tampa Bay Buccaneers for 20 years, the elder Culverhouse also made millions in banking and real estate. That includes Palmer Ranch, which Hugh Sr. bought from the heirs of the Palmer family in 1974, some 12,000 acres for $12 million. But controversy often followed Hugh Sr., even after he died, in messy inheritance disputes littered with debt. 

Culverhouse says his father “was addicted to debt, likely driven by insecurity and a desire to appear wealthy.” Palmer Ranch, the Buccaneers, an airplane, a boat, an orange grove and a water and sewer plant — it was all purchased, he says, with borrowed money. When he died in 1994, the senior Culverhouse owed over $300 million to multiple banks. So, the junior Culverhouse spent the next four to five years settling his father’s debts by selling off most of his assets — except for Palmer Ranch and the condo where his parents lived.

Culverhouse Jr. received approximately 10% of the Palmer Ranch property on his father’s death and 38% through gifts over the next five years from his mother, Joy Culverhouse. He then bought the remaining 52% of Palmer Ranch from her for approximately $40 million. He took on some debt to buy out his mother’s interest in Palmer Ranch — but he proudly says he’s paid it all off through land sales. 

Culverhouse has criticized his dad publicly for some of the choices his father made, including the debt. And he admits his relationship with his mom was complicated. Even so, he can trace one trait he has today to his mother: resilience. 

One story Culverhouse tells goes back to a fight he got into, at, of all places, a Boy Scout meeting while growing up in Alabama. Culverhouse says he was getting whipped. Crying, he found his mom in the crowd. She told him to get back in and fight. He did. And with a roundhouse windmill punch, Culverhouse knocked down his young rival. 

Culverhouse caps the story of the fight on Alabama dirt 65 years ago with a dig: “I’ve always been against bullies,” he says, “and like most bullies, when you hit them hard, they fall apart. Just like most politicians in Sarasota County.” 

Photo by Lori Sax

Later on, when Culverhouse was a federal prosecutor, his mom, again, motivated him. This was after Culverhouse had lost his first four trials. He called his mom and told her he was going to quit. This after getting out of tax law (too boring, he says) and interviewing with 30 other U.S. Attorney’s offices for a prosecutor job before finally landing the one in Miami. 

A champion college and amateur golfer, Joy Culverhouse wasn’t having it. 

“She said a bunch of curse words and then said, ‘Hugh, if you ever talk about quitting again, I’m coming down to Miami, and I’m going to beat you senseless with a two iron.’” 

Culverhouse didn’t quit. And his mom’s reward: His son funds a scholarship at the University of Alabama aptly named the Two Iron Club. 

Local hero

Another side to Culverhouse’s giving philosophy comes down to what’s essentially his shrewd approach to life, business and decisions.   

That can be traced, in one sense, to Hugh Sr. and the late 1960s when Culverhouse Jr. was thinking about college. His dad offered to pay for school — with a practical caveat: “‘My dad said, ‘You can either go to college and major in accounting, or you can go to Vietnam. But you’re not going to college to major in history.’” 

Ditto for the practical approach to Palmer Ranch. Culverhouse was on the boards of a few homebuilders for several years, but he learned, he says, that developing the land to sell to homebuilders is a much better way to make money. 

“Homebuilders have too much risk,” he says, and are too beholden to banks. (Palmer Ranch is now a thriving master-planned community, with more than 90 subdivisions and a host of commercial, retail and assisted living facilities. Some 20,000 people live on Palmer Ranch, which is south of Clark Road and covers about 60 square miles. The community is also not yet totally built out, with more projects in the pipeline) 

Some of his most recent donations in Sarasota follow that shrewd, or what Culverhouse might call his practical, common-sense, outlook on life. That’s how he connected with Embracing Our Differences, after reading that Sarasota County commissioners cut some of the organization’s funding. Cuts approved by Sarasota County commissioners also led Culverhouse to give $100,000 to Legal Aid of Manasota in September and $109,000 to the United Way Sarasota in May to preserve the 211 helpline. 

Some county commissioners were quoted in local media publications saying the United Way cuts were due to that organization funding groups that perform or support abortions. “When (commissioners) did that, I said, ‘All you are doing is being vindictive,’ and that’s something that I couldn’t sit with. I wasn’t going to sit still and let that happen.”

Last year Culverhouse gave $150,000 to shore up state and local funding for the Comprehensive Treatment Court in Sarasota County. Sarasota County Judge Erika Quartermaine founded the CTC in 2017, designed to deliver services to individuals who commit nonviolent offenses and suffer from severe mental health disorders. 

Culverhouse had heard about the program — and its funding predicament — and reached out to Judge Quartermaine. They met for what turned into a 90-minute lunch at Mediterraneo on Main Street in downtown Sarasota to talk about it. Quartermaine was impressed by how much research Culverhouse had done and was pleasantly surprised with his optimistic outlook. “I think his intention is so pure,” she says. “And, without being trite, I really think he wants to make the world a better place.”