Emerging from a crowded CD 19 field, here’s the path Byron Donalds beat on his way to national esteem
Byron Donalds wins one of the most expensive GOP races in the country. Image via Donalds campaign.

Byron DOnalds
Self-funders and long-established pols couldn't stop his rise.

It was less than three hours between when polls closed and media outlets called the primary in Florida’s 19th Congressional District. Naples lawmaker Byron Donalds, a self-described “Trump-supporting, gun-owning, liberty-loving, pro-life, politically incorrect black man,” had won the GOP nomination.

It ended up being a close race, one that came down to a 774-vote lead on Cape Coral lawmaker Dane Eagle out of 103,915 votes cast. Donalds nearly set a record for lowest share of the primary vote to secure the nomination.

The race was over, but not before a chaotic day in which the Donalds camp panicked over a dirty trick widely attributed to the Casey Askar campaign that could have unraveled almost a year of hard work.

Yes, the headline-inducing onslaught of this GOP primary did last less than a year. Back before negative flyers stacked up in district mailboxes, before a dozen different Republican candidates went as far as opening campaign accounts in the race, before anyone in America learned the medical term COVID-19, the race started with Rep. Francis Rooney tacking an almost off-hand announcement at the end of a Fox News interview.

It will actually be a few months before Donalds can unapologetically take a full victory lap. But the race to get this far is already one for the ages.

Onslaught of Interest

It was during a weekend newscast when Rooney, a second-term Congressman and former U.S. Ambassador to the Holy See, let people know he would not seek a third term. National news interest in Rooney had increased when he became one of a handful of Republicans in the House to say they were open to hearing the case for impeaching President Donald Trump. With such a stance generating backlash on the right, Fox News host Leland Vittert asked a question Southwest Florida voters most needed answered: Should the media put Rooney on a list as one of the Republicans not seeking reelection in 2020?

“Yes, you do. I’ve done what I came to do,” he told Vittert on “America’s News HQ.”

And with that, the cell phones of consultants in Southwest Florida started buzzing. Who would run in a region filled with conservative leaders? Virtually every state lawmaker, County Commissioner and major Mayor in coming weeks would go on record in Florida media jumping in or bowing out.

Notably, a local black conservative not named Byron Donalds was the first to file. Antonio Dumornay filed quickly but would eventually decide the primary was going to be too expensive. By the candidate qualifying deadline, he had left the race entirely.

The first candidate with longevity would be Dr. William Figlesthaler, who promised to self-finance a competitive race (and did follow through).

Eagle became the first well-known elected official to enter the race. He would be joined by state Rep. Heather Fitzenhagen and Fort Myers Mayor Randy Henderson. But Donalds pondered the decision longer than his peers — at least as far as opening a campaign account.

The lawmaker started to bring together an inner circle as early as October. Donalds had run for Congress in 2012 but backed out of a crowded field at the time. He called up some of the people who had helped him with that run, along with those who worked on his House campaigns in 2016 and 2018. Donalds’ wife, Erika, a former Collier County School Board member deeply active within the national school choice movement, tapped her network as well.

Shawn Frost, a political consultant who knew the Donalds through the American Federation For Children, jumped to action when he learned of Donalds’ ambition, putting other projects on hold.

”When the Donalds family asks me to do something, I make it happen,” he said.

The Donalds team ultimately decided to forgo the fourth quarter of 2019 and jump into the race formally in January. When he did file, a launch video went viral and he found himself on the couch in the New York studio for “Fox and Friends.”

But Donalds’ star power wasn’t yet enough to scare off a large field of candidates.

Conservative pundit Ford O’Connell dipped his foot in, though he backed out as COVID-19 sent the economy into a tailspin. Disabilities advocate Darren Aquino, anti-abortion activist Christy McLaughlin and Sheriff’s Deputy Daniel Kowal jumped in as well.

And then there was Askar, a fast food magnate who got into the race late and largely adopted O’Connell’s campaign team.

At various times, 12 candidates had active FEC accounts, and 10 qualified for the ballot.

Into The Unknown

As with every race in America, COVID-19 posed challenges for door-to-door campaigning unlike anything in living memory.

Donalds said the pandemic created more obstacles to the campaign than anything else in the race.

“COVID threw a big wrench into it and made it difficult to organize,” he said. “We didn’t have an election office, and usually, that becomes a hub of energy that created connectivity with volunteers. We did it in a digital framework, and that’s one thing that threw me for a loop.”

Figlesthaler, who had introduced himself to voters as a successful businessman and political outsider, donned a white lab coat to announce he was shifting his campaign into public service mode while Eagle used campaign dollars to support town halls.

O’Connell folded up shop amid the sudden financial calamity of the pandemic. Aquino briefly contracted the coronavirus. Candidates including Fitzenhagen, Henderson and Donalds weighed in on local decisions around lockdowns and mask mandates. Eagle began handing out free masks while going door to door, something that awed some competitors and made others scoff.

Askar in one sense thrived in the lockdown. With the best funded of the campaigns, he hit the airwaves with autobiographical ads produced with Axiom Strategies that introduced Askar to voters locked at home with only their laptops and television sets to keep them busy. The effort raised the candidate from anonymity to the top of the polls by early July.

By then, Fitzenhagen abandoned the race, opting instead for a state Senate run, notably teaming up with the same Axiom consultants working with Askar.

The rest of the elected officials in the race began jockeying for attention from outside groups in Washington. Chasen Bullock, the consultant for Henderson, could sense a single force might thumb the scales in a substantial way.

“Club for Growth has done a very good job around the country of making calculated decisions and going all in,” he said.

Terry Miller, campaign manager for Eagle, said his candidate met with Club For Growth and other major players like Americans For Prosperity, which had a strong presence in Tallahassee state politics as well. Miller counted on the fact than an electorate disappointed with a series of short-timer self-funders would seek out a reliable voice this year.

“Ultimately, voters looked at the two candidates with legislative experience and those were the top two,” he said, believing the Donalds-Eagle finish as vindication of an “Experience Matters” motto.

Consultants for other campaigns, though, questioned whether the experienced conservative label fit baby-faced Eagle.

Donalds instead cast himself as a fiery Trump-loving conservative, which proved successful with voters whose minds as much as anything are on the Presidential election this year.

That seemed to attract outside forces as well. Both AFP and Club For Growth’s political arms endorsed Donalds, paving the way for millions in outside spending to make its way to the Fort Myers-Naples market.

“Our goal was always to make this a national campaign,” Frost said, “and we did.”

Oppo Overflow

More than a month ahead of the primary, everyone’s biography had been put before voters, and the outside players had picked their horses in the race. While the early days of the race had seen some attacks on candidates — a DUI for Eagle from 2014, a key to the city Henderson as Mayor gave to controversial Democratic U.S. Rep. Ilhan Omar — these ads turned to the airwaves and reached a mass number of voters.

Honesty America, a Super PAC formed by Matt Pusateri, a close associate of Askar consultant Nick Carr, unleashed attacks on Donalds’ criminal record. While Donalds preemptively included stories of life as a Brooklyn teen who got in trouble with the law, the new ads painted him as untrustworthy thanks to marijuana and bribery arrest dating to his early 20s.

It also labeled Donalds as a Never Trumper. Donalds scoffed at the attack during a press conference with social conservative leader John Stemberger, noting he spoke at multiple Trump rallies in 2016. But the ads pulled up Facebook comments from 2011 of Donalds calling Trump a distraction and speaking better of Carly Fiorina, a former GOP candidate who is now voting for Joe Biden.

It also noted Donalds supported Mitt Romney for President in 2012, a humorous attack because within weeks, ads hit Askar for donating to Romney that year but doing little for Trump.

“What Republican didn’t support Romney,” an Askar response ad would later state while also dismissing the Utah Senator as a “traitor” for supporting impeachment.

Meanwhile, every bit of Askar’s personal backstory came under the microscope. A Navy document began to circulate questioning whether he had served in the Marines; Florida Politics confirmed he did four years before a discharge but left as a private with few awards. Divorce papers called into question both Askar’s presentation as a family man and his handling of a business merger in Michigan. And a complaint was filed saying Askar overstated  he graduated from Harvard Business School when he actually earned a certificate through an Owner/President Management program.

Figlesthaler’s past business relationship with a doctor arrested for child porn fueled its own criticism, eventually getting cut into an Honesty America ad alongside pictures of his fourth wife and assertions the doctor’s campaign was simply a midlife crisis. Figlesthaler’s team dismissed the story as a smear, noting Figlesthaler testified against the physician arrested at his practice.

Club For Growth also swept in with ads both boosting Donalds’ personal story and attacking the other poll-topping candidates: Askar, Eagle and Figlesthaler. It turned into a bitter race raising trepidation among voters. But about that time, it also became clear the nine-person race had effectively become a four-man battle.

The Figlesthaler campaign opted not to spend on negative advertising as the tone of the race slipped further into negative territory. But there was little need. Between Club For Growth, Honesty America and various newly formed Super PACs like Trusted Conservatives and Concerned Conservatives put every misdeed from the top four candidates’ lives on full and constant display. Dashboard camera footage from Eagle’s DUI stop appeared on multiple mailers, as did details about Figlesthaler’s business partner, Donalds’ arrest record and Askar’s various dodges about his own background.

Professional consultants and volunteers at the Donalds camp tried to keep perspective. Eight internal polls conducted over the course of the primary by the Donalds team all showed him in the lead. So did two out of three St. Pete Polls surveys commissioned by Florida Politics, with the third putting him in second place. An internal Eagle poll that showed the Cape Coral politician winning also found Donalds in second place.

Frost said working with forces like ColdSpark’s Mark Harris helped keep the Donalds message on track. The camp secured a critical endorsement by the National Rifle Association, one of three gun rights groups that ultimately backed Donalds; the NRA also took Eagle to task for his role in shaping the Parkland bill that raised the age to buy long guns in Florida.

Donalds, for his part, was braced for many parts of his record to be attacked. But it took him aback when some “outright lies” ended up on television ads. Askar, for example, said in a campaign ad that Donalds supported President Barack Obama in 2018.

“Anybody who has examined my political history knows that’s not the case,” said Donalds, who has told the story of how he upset his own mother by voting for John McCain over the first Black President. “To just make something up out of thin air. The only this that really surprised me, outside of COVID, was that we know campaigns get hard and things get tough sometimes, but I didn’t think it would get this nasty.”

Election Day

Nevertheless, Donalds woke up on Election Day hopeful. Frost felt confident Donalds would win but was nervous at the hundreds of thousands of dollars poured into marketing during the last week by Askar’s campaign. Then a mass text message rattled the race hours before polls closed. Voters through the district felt phones buzz at the news Donalds was dropping out of the race, a complete lie.

Donalds immediately fingered Axiom founder Jeff Roe and the Askar campaign, noting Ben Carson in 2016 had accused the Roe-headed Ted Cruz campaign of spreading a similar false rumor at the 2016 Iowa caucuses. Financial disclosures later showed Honesty America dumped $29,750 in a last minute expenditure with the North Fort Myers marketing firm tied to Pusateri and which offers text messaging services.

Askar’s team denied any involvement in the text messages, accusing either the Eagle campaign of the stunt (Miller called the move unethical and unacceptable) or the Donalds campaign itself. Frost finds the latter especially laughable, suggesting such a high-risk play for sympathy that might put the whole campaign at risk. Such an action made no sense because of a high probability it could backfire. But after news broke of the texts, Club For Growth jumped in and paid for an extra 80,000 texts to be sent out supporting Donalds campaign.

Certainly, the entire episode made for an anxious final day on the trail.

“I didn’t know what was going to happen,” Frost said.

That didn’t stop when polls closed at 7 p.m.

Absentee totals revealed the race might not be between Donalds and Askar but Donalds and Eagle, with the former doing well in his home county of Collier while Eagle dominated his own Lee County turf. Miller, famous for solid ground game in Lee, hoped Eagle might stun the pollsters through old-fashioned door-knocking. And at one point in the night, the Cape Coral pol held the lead district-wide.

But through most of the evening, totals favored Donalds. He ended up winning the district by 0.75 percent of the vote, just enough to avoid a mandatory recount. When his lead exceeded 700 votes, Florida Politics called the race in Donalds’ favor. While Miller sat at Eagle’s home watching results roll in, the two braced for a closer call, but it slipped away. Fourth place Figlesthaler was actually the first to call Donalds and concede, but Eagle’s call came shortly after.

“We didn’t win but we were going to lose like gentlemen,” Miller said.

The next day, Eagle met with Donalds at the Republican headquarters in front of gathered press and issued a public endorsement, a gesture deemed gracious and magnanimous by the Donalds team.

Later that day, Donalds received a call with a 202 area code that he picked up, anticipating a Washington group eager to join the now-GOP nominees team. It turned out to be the President of the United States.

Frost recalls how in all the wooing of Washington forces, the one elusive bit of support that never materialized pre-primary was “the tweet,” backing from Trump. But Donald Trump Jr. tweeted about Donalds victory, and the call discussed plans to put Donalds on the stage with the President during the reelection campaign.

Even Donalds’ former opponents say the Naples Republican holds national star potential. “He should be flown around the country and appear with Trump at every rally,” says a rival consultant.

Of course, there’s still a race on in CD 19. While the district tilts deep red (Rooney won with 62% of the vote in 2018), Donalds faces Democrat Cindy Banyai in November, who had her own surprise victory Tuesday. The two appear for their first debate Friday at Cantina109.

Jacob Ogles

Jacob Ogles has covered politics in Florida since 2000 for regional outlets including SRQ Magazine in Sarasota, The News-Press in Fort Myers and The Daily Commercial in Leesburg. His work has appeared nationally in The Advocate, Wired and other publications. Events like SRQ’s Where The Votes Are workshops made Ogles one of Southwest Florida’s most respected political analysts, and outlets like WWSB ABC 7 and WSRQ Sarasota have featured his insights. He can be reached at [email protected].


  • Hopeful

    August 24, 2020 at 1:16 am

    Great look at this race. Rep. Donalds was one of the smartest people in the state legislature and those years are still fresh enough to hold out hope that having to degrade himself over who is more slavish to Donald Trump to secure the plurality of a base election was simply electioneering – the typical kayfabe sold to the rubes ala DeSantis ‘18. Lots of GOP professionals seem high on their own supply these days though. Time will tell. The DeSantis playbook is working so far.

  • freedom fighter

    August 24, 2020 at 10:51 am

    He is unique, and speaks eloquently; but no representatives of the people and by the people should be viewed as “stars” or put on pedestals.

    Please learn more at KrisAnneHall.com to #EducateAmericaAgain

  • John K. Thomas

    August 25, 2020 at 11:23 am

    Great post by Ogles. Byron is a unique conservative talent. His very compelling message will resonate with Americans and help bring home a Trump victory. Watch his popularity soar during his freshman year in the US House of Representatives.

Comments are closed.


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