'Our mini Trump': How Republican farmer Alfie Oakes became Collier County's kingmaker

Alfie Oakes knows how to grow.

The Naples farmer-turned-grocer-turned-restaurateur’s flagship Seed to Table is a $30 million produce-centric destination he calls a "culinary universe."

Behind it is the muscle of Oakes Farms, one of the biggest agribusinesses in south Florida, started when its namesake was a 15-year-old selling watermelons from the back of a pickup. He's grown it into a 3,500-employee empire that ranges from supplying military cafeterias to selling linen sundresses.

Oakes, 55, also has grown a reputation as one of the region's most powerful political influencers.

In this deep red region, Seed to Table has become the clubhouse for a rising group of Make America Great Again Republicans. United under a pro-Trump, anti-vax, America First banner, all seven of “Alfie’s Freedom Picks” handily won their seats in Collier County's 2022 elections. He footed the bill for two busloads of Trump supporters headed to Washington, D.C. on Jan. 6, 2021 to what Oakes called "the most peaceful beautiful demonstration from well over one million people that I've ever witnessed."

In Collier, he’s found fertile ground for his anti-establishment views: Oakes recently lent his cred to the successful push to get Collier County to stop fluoridating its water.

Tight black T-shirt setting off his megawatt grin – “Forty years I haven’t had a cavity” – he told commissioners mass administration of the mineral, which the CDC says protects teeth from decay, is part of a globalist movement to medicate the population into submission. “If you don’t think this is intentional to dumb us down, to keep control of the people in this country, then I don’t think you’re paying attention … We don't trust the white coats anymore.”

'Local boy done good'

Though some of Oakes' sentiments may make old-guard establishment Republicans wince, their respect for his passion is plain.

“The big picture for Alfie is ‘local boy done good,’ “ said fellow Republican and former Florida Rep. Matt Caldwell. “When all is said and done, he has been incredibly successful because he’s willing to work hard and do what it takes. It's not as common these days as it used to be.”

Though Oakes hasn't yet run for a government position, he holds elected office: Collier's Republican State Committeeman.

If his political aspirations extend beyond that, he hasn't told the Naples Daily News, which tried multiple times and ways to reach him for this story. That didn't surprise Caldwell, now Lee County's property appraiser. “Fairly or unfairly, traditional media is highly distrusted by a wide swath of political figures these days,” Caldwell said.

Some Alfie-watchers are expecting more from him.

"I think he’s going to become active on a bigger stage,” said Michael Thompson, former state director for the America Project's Florida for America First and now chair of Lee County's Republican Executive Committee. “Alfie’s got a lot of support, a lot of followers, a great understanding of what our country needs, so I fully expect him to do something in the next few years. What? That’s the million-dollar question.”

Others wonder at what appears to a retreat from the public eye: "Alfie seems to have kind have gone underground or off the radar screen in the past year or so,” says Peter Bergerson, Florida Gulf Coast University political science professor emeritus.

Freezes, failures and a father's organic dream

Francis Alfred Oakes III was born in Delaware City, Del., on June 16, 1968, according to his Facebook profile. When he was 5, his family pulled up stakes and moved to Florida, settling into an east Fort Myers duplex after his father Frank Jr.’s produce business had failed.

He grew up working at his father’s small store in east Fort Myers before starting his own enterprises as a teenager. Weekends, while North Fort Myers High School friends were hunting or fishing, Oakes was commuting to Immokalee to buy produce, then sell it at the foot of the Cape Coral Bridge or the corner of Pine Island and Pondella roads in North Fort Myers.

When he was 18, he opened Hancock Farm Market on Hancock Bridge Parkway. He hired a cashier named Deanne, then he married her. They had three children: Dain, Kyle and Hannah.

In 1989, Oakes leased 40 acres to grow zucchini. That Christmas Eve there was a killing freeze, one of the worst of the last century. It wiped him out. After a friend told him tomatoes were cheap in Honduras, he gathered his $20,000 life savings, borrowed $25,000 more and flew down with his friend to check it out.

Five years later, Oakes had a dream that he should plant cucumbers. "I never had had a dream like that, but I decided to do it," he later told the Naples Daily News. He leased 40 acres in Punta Gorda, planted the cukes and wound up getting some of the highest prices anyone had seen in years.

It was 1994. With the profits, father and son created the Oakes Farms store at 2205 Davis Blvd. in Naples. Frank was committed to organics, but the pricey-to-grow veggies were a money loser, and his father gave up, leaving Oakes to cover $300,000 in bad checks and keep the store running, he later told the paper.

"Until 2005, I was working seven days a week," Oakes said at the time. "Sometimes trucks which were delivering produce had to wait for hours until we had enough in our cash registers to pay them."

But father and son continued to make plans. On Feb. 2, 2013, they sat down to a dinner of mashed potatoes and gravy and worked out details for an expansion. The next day, Frank Oakes had a heart attack and died. He was 66.

"What hit me is that about 2,000 people came to his funeral," Oakes later told the Daily News. "Several people told me that they felt closer to him than they did to their own parents. That was life-changing for me."

Caldwell doffs his hat to Oakes' success. “Cut-throat doesn’t begin to describe vegetable sales,“ he said. "He dove in head-first and earned it the old-fashioned way – he was buying at the seconds market in Immokalee and selling it from the back of his truck. Like an old-fashioned American story, he just kept working harder and harder, building it up and looking for opportunities."

In 2016, Oakes said, “My wife asks me, ‘Where does it stop?’ I don’t know. Things keep popping into place. It’s not planned; it’s wherever it guides you.” One thing he was sure about: His father would “be really happy with what we’re doing here. I don’t know if it’s my dad looking down at me, but we keep doing amazing things.”

Viruses and vegetables

Oakes and COVID-19 have had an uneasy relationship, by turns productive and destructive. The same week China announced the outbreak of the virus in the city of Wuhan, Seed to Table opened, points out David Silverberg, Naples political pundit, and former managing editor of The Hill.

In short order, Oakes drew both praise and fire after he told columnist Phil Fernandez the disease was bogus, then took Collier County to court for its mask mandate. (That Oakes’ business depends on farmworkers, among those hardest-hit by the disease, was a point emphasized by the protestors who soon turned up to picket.)

“He was not a public figure prior to COVID," Caldwell notes. "I think like a lot of people, he was affected financially by the COVID policies; he felt strongly on a political level and felt compelled to speak out and that’s only grown in terms of his engagement in political issues.

In June of 2020, Oakes posted on Facebook that COVID-19 and the Black Lives Matter movement were hoaxes. He called George Floyd, a Black man who died in police custody in Minneapolis the previous month, a "disgraceful career criminal."

Some rallied to Oakes' defense, but Lee and Collier school districts, who'd bought his produce, faced fierce backlash. Petitions circulated. Protestors gathered. Lee County cut ties with Oakes Farms. Oakes lawyered up, claiming that severing the three-year, $6 million deal was breach of contract, plus an infringement of his First Amendment right to free speech. Two months later, Oakes ran for and won Collier County's Republican state committeeman office, defeating Naples attorney Doug Rankin, who’d served since 2008.In April of 2021, part time resident, rocker, gun-lover and COVID skeptic Ted Nugent visited Seed to Table. The Motor City Madman played a little, talked some politics and a week later, tested positive for COVID. "I thought I was dying," he told a Facebook live audience.

In March of 2022 Oakes was arrested at the Seminole Hard Rock Hotel & Casino Hollywood. He was trying to cash in his chips, but he refused to provide identification, a Seminole Police Department spokesperson said. "(Oakes) allegedly attempted to approach security staff in an aggressive manner," Seminole Police spokesperson Gary Bitner told the Naples Daily News. "While being handcuffed, he allegedly tensed and pulled away from officers."

Oakes was booked into Broward County Jail, then was released on a $25 bond.

Tell me you're a kingmaker without telling me you're a kingmaker

Later that year, Oakes was in high campaign gear, hosting fundraisers and events for his hand-picked Collier candidates for offices ranging from the school board to county commission to get them before voters.

His investments paid off.

Every Collier candidate he’d backed won. “Clean sweep for Oakes in ‘22 primaries,” his website announced. “Kelly Lichter, Jerry Rutherford, Timothy Moshier reaped the benefits of the endorsement of Alfie Oakes and his loyal supporters who backed America First candidates,” the post underneath the headline began.

"Kingmaker" is the first word Kari Lerner, Lee County Democratic party chair-turned Congressional district 19 candidate settles on when asked about Oakes. “And of course, he did fund two buses to what became an insurrection attempt. As far as Alfie Oakes personally, I have not met him (but) I would be interested in sitting down with him and having a conversation,” she said. “We need to stop the divisiveness … Division is weak and unity is strength.

“Calling our fellow Americans vermin and enemies – that is not the America that has been great,” she said.

Caldwell takes the kingmaker label with a grain of salt. “Having been either lauded or accused of being a kingmaker myself at times, it’s like most things,” he said. “When you step out and put yourself in a position of leadership, you get credit and blame – mostly for things you have nothing to do with.”

What happens when one of Oakes' annointed goes against him? It can get nasty, Silverberg says.

It earned Collier school board chair, Kelly Lichter, one of "Alfie's picks" the "traitor" label after she backed a superintendent Oakes opposed. “She'd just voted for who she thought was the most qualified person,” Silverberg said. "And Alfie sued the school board."

Oakes claimed the school board violated the Sunshine Law by letting a search firm select 10 candidates from 45 applicants privately, without public notice, public comment or minutes."All I want is a fair process," Oakes told the Daily News at the time. The board argued the search firm only had power to fact-find and advise Collier Circuit Judge Joseph Foster denied Oakes' motion and the board approved Leslie Ricciardelli's contract, which left Oakes fuming, Silverberg said.

The episode reminds him of the 45th president, who also hurls vitriol at those who disagree with him. "He's our mini-Trump," he said, a point he made in a 2022 Mother Jones piece, "The MAGA Grocery King of Southwest Florida."

That's just fine with area Republicans, like John Meo, chair of Collier's Republican executive committee: "He and Trump are motivated, driven to accomplish goals and by love of country."

Bergerson sees the resemblance too. Like Trump, he says Oakes "represents a different vein within the Republican party." Though the region has long been a GOP stronghold, "it's tended to be much more staid. (Oakes) has really turned it into a very vocal and in some ways vitriolic strain ... I think he sees the government and the deep state as the problem, so it’s us versus them.”

'Good Republicans and not-so good Republicans'

The polarization has seeped into Collier County from outside, believes longtime County Commissioner Burt Saunders. "I think a lot of that can be attributed to national politics where there are perceived to be good Republicans and not-so good Republicans," he said. "You see that in Washington all the time, but it’s my hope we don’t see that in Collier County."

"I think in the long run, people are a little bit tired of Republicans denigrating other Republicans just because they happen to disagree on a particular issue," he said.

Saunders is quick to say he doesn't know Oakes at all. "He’s brought political issues before the board he’s been very passionate about, but in terms of him personally, I don’t know anything about him."

He does know running afoul of Oakes can have consequences. "I have not, on occasion, voted the way he’d have liked me to have voted and he’s even indicated at a board meeting that if I didn’t vote the way he wanted me to on a particular issue, then I would not be able to count on any support," he said. "Of course, that did not change my vote."

The difference between Oakes' passionate crusading and his own pragmatism is philosophical, Saunders says.

"For me, the Collier County commission has a certain jurisdiction, a certain power, a certain authority, and I like to stick to what our mission is,” Saunders said. “That mission basically is zoning, water service, sewer service, garbage collection, roads, police protection, emergency medical services – there’s a list of things that are really in our jurisdiction and I don’t like getting outside of that. So, there are going to be issues that perhaps Alfie and some other folks are going to promote that I just don’t think should be in front of the county commission. So that’s where we have our disagreement, but there’s nothing personal."

He also knows Oakes may be gunning for him come next election. "I anticipate that and respect his ability and right to engage that way," he said. “When you go into the voting booth, you vote for the Republican you think is best suited for the position you’re voting for, but that doesn’t make the other guy necessarily a bad Republican – you just happen to have different views."

This article originally appeared on Fort Myers News-Press: Alfie Oakes: How a farmer became powerful GOP influencer in SW Florida