PLANTATION, Fla. — Republican U.S. House candidate Casey Askar, a pizza maven and entrepreneur, lives about a 5 mile drive from the district where he is running, one of four that the Florida state GOP redrew to favor their party.
His home is an extravagant mansion where he cannot be seen, isolated behind a massive gatehouse. The residence could serve as something of a metaphor for his campaign for Florida’s 22nd Congressional District, where he also is not especially visible, has spent a lot of his own money and still might lose to his Democratic opponent, Pia Dandiya.
“I haven’t seen him around here at all,” said Republican Florida state Rep. Anne Gerwig. She represents Wellington, one of the largest municipalities in Palm Beach County, one of four counties encompassed by the 22nd District.
The new district map that Republicans crafted got rid of one of the largest Democratic seats in South Florida, the 20th Congressional District. The majority-Black seat was represented by former Rep. Sheila Cherfilus-McCormick and created in 1992 by a federal court as a remedy for racial exclusion. It is one of the four GOP-leaning seats that Republican Florida Gov. Ron DeSantis enacted in May, along with those held by Democratic Reps. Kathy Castor, Jared Moskowitz and Darren Soto.
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On the cusp of the midterm elections, the partisan gerrymandering looks like it may have backfired, with just Soto’s 9th District considered likely to fall to Republicans by the prognosticator Cook Political Report.
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Castor and Moskowitz may overcome the unfavorable maps thanks to souring prospects for the president’s party and the advantages of incumbency. But the 22nd District, a so-called “Frankenstein district,” was supposed to be a GOP-friendly blank slate stretching from the west sides of Palm Beach and Broward counties into Republican-leaning territory in more rural areas and into Hendry County and southern Collier County.
Askar seemed to be a good fit. An Iraqi immigrant whose legal name is Kousay Askar, he paints himself as a product of the American dream: A Medium post he wrote says his family immigrated to the U.S. to escape religious persecution, he enlisted in the U.S. Marines after graduating high school, and ultimately became a businessman and restaurant franchise owner. According to his financial disclosures, his net worth ranges anywhere between $97.5 million and $480.5 million.
The district that Republicans created has more registered Republicans than Democrats, and President Donald Trump would have won it in 2024 by 11 points.
What looks good on the surface, however, doesn’t always translate. When the Cook Political Report moved the race from “lean Republican” to “toss-up” in September, the analysts pointed out Trump would have lost it by three points in 2020. And 2026 is looking a lot more like that year.
Then there’s the problem of Askar’s campaign style. The candidate Republicans picked to fill that blank slate seems to be, well, leaving it blank, ceding the public spaces to Dandiya, a former educator and Apple lobbyist on education issues.
For instance, Gerwig told The Washington Sun that her friends in the area have yard signs for Dandiya “at their homes” in the eastern side of the district. Asked whether she had seen any signs for Askar, she said, “I haven’t seen them around here.”
Dave Shepard, a resident of Marco Island south of Naples, a Republican stronghold on the western side of the district, said he votes for Republicans “most of the time” but that he could not name Askar “off hand.” He told The Sun he had seen plenty of political yard signs for city council races but hadn’t noticed any for Askar. None of the voters interviewed for this story said they had attended or seen an Askar campaign event in their community.
Askar also does not appear to have a headquarters for his campaign, with the only physical address available on public records being a UPS Store P.O. Box in Naples outside of the district, about a 10 minute drive from Askar’s house in Naples’ Port Royal neighborhood.
No one appeared to be home when a Sun reporter went to Askar’s house, and he did not respond to a note left in his mailbox after multiple attempts to reach him by phone and email.
While Askar has been pictured at some local events, some only for registered Republicans, there are no public ones listed on his campaign website. The Florida Republican Party and the four Republican county parties in the district did not have any events with Askar in the last week before the election, and a website listing events in Southeast Florida did not show anything with Askar.
Republican Rep. Mario Díaz-Balart, whose district lost portions to the 22nd District, told the Sun he has run into Askar at different events in Broward County, saying that “he is working.”
One Democratic operative, who was granted anonymity to talk about campaign opposition research strategy, told The Sun that even political trackers paid to trail candidates are having a hard time finding Askar because of his lack of public appearances.
The campaign knows it has a problem, at least judging by what the candidate has said out of sight. In an audio recording obtained by The Sun from a mid-October voter meet and greet in Broward County organized by a local Republican group, Askar said that an internal poll conducted with the National Republican Campaign Committee against Dandiya found him “down about five and a quarter points.”
“Don’t be afraid of this,” Askar told attendees, before introducing the poll. The Sun did not review the poll Askar mentioned.
Republicans have not released any polling on the race, but House Majority PAC, the flagship House Democratic super PAC, found Dandiya leading Askar by two percentage points in a head-to-head matchup in a September poll.
The NRCC did not answer questions about polling, instead ripping Dandiya as a “radical Democrat” who will be rejected by voters.
What Askar is doing is dumping money into TV advertising in the general election: over $2 million, according to campaign records. Dandiya has spent $2.2 million for TV advertising, according to campaign records. The race is the third-most expensive House race in Florida. Outside groups are also spending heavily.
An air war in the sprawling district does make sense, said Michael Worley, a Democratic strategist and CEO of the Florida-based political and public affairs firm MDW Communications, which is working with Dandiya’s campaign. “TV has to be the most effective” way to campaign across the district’s three large and expensive media markets: Fort Myers, West Palm Beach and Miami.
One Florida Republican operative, also granted anonymity to speak about Askar’s presence, said that his campaign also has flooded the strongly Republican Naples area with mailers and text messages, but he has not held any rallies.
Askar’s physical absence and media shyness is costing him more than local recognition.
Michael Napoleone, the Republican mayor of Wellington, broke with his party and endorsed Dandiya. He said part of the reason he did so was because Askar has refused to respond to news outlets’ requests for comments and interviews.
It “is very telling to me sometimes because more and more often, certain people, they just don’t want to respond to valid questions that voters want to know the answer to,” Napoleone said. “That does a disservice to the voters if you’re not willing to sit down and answer what might be hard or uncomfortable questions.”
Worley argued a campaign that relies mainly on television advertising without a ground game, “90% of the time, that does not work.” He pointed to Democrat Jeff Greene’s 2018 governor race, whose campaign prioritized media advertising over on-the-ground efforts. He finished fourth in the Democratic primary.
Like Greene, Askar is also a largely self-funded candidate: He has loaned his campaign over $6.6 million, about $3.5 million just in the general election.
Most of Askar’s TV ads, as well as those from outside groups, have focused on attacking Dandiya. They appear to have helped the Democrat’s name recognition rather than his own. The Sun spoke to 28 voters in Marco Island, most of whom said they did not remember Askar’s name. They still planned to vote Republican. One voter who declined to be named, for example, said, “I know not Pia,” when asked who they’d be supporting in the race.
Dandiya, who also lives outside of the district, has been trying to fill the hole left by Askar, holding many more events and out-raising him significantly through traditional fundraising. In the third quarter, Dandiya hauled in more than $1.3 million compared to $321,000 for Askar.
Dandiya said that she has done over 70 meet and greets with voters “and I am so grateful to have met those folks in the community and to understand their needs.”
“That’s been essential because how are we going to know what to fix and how to fix it if we’re not talking to people and listening to people?” she added. “My opponent has not been very visible in the district. … That seems to be the theme of his campaign, that he wants to not really be a representative; he wants to be a rubber stamp for Trump.”
Dandiya held a rally Monday in Plantation with former Secretary of Transportation Pete Buttigieg, a potential presidential candidate in 2028. He’s one of multiple Democratic surrogates that have traveled to the district, including potential 2028 contender Rahm Emanuel and Reps. Jamie Raskin and Suzan DelBene, the chair of House Democrats’ campaign arm.
Democrats say they are feeling bullish about their chances in the district, even with redistricting.
“This district was drawn specifically in order to give an unfair advantage to Republicans,” Buttigieg said. “Instead of trying to persuade the voters, their strategy is to rearrange the voters so that they can pick their voters instead of the other way around. But I think we’re going to win anyways and when we do it, it will send a very powerful message out to those guys.”
“Think about the shock waves that will radiate through this country when we win in this district,” he added.
Trump held a rally in the neighboring district to boost GOP turnout in the state last Friday.
Askar wasn’t visible there, either.
This story was updated to specify Dandiya’s area of lobbying.
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