The SWFL legal landscape: Askar vs. Donalds to go to a jury; Oakes seeks facetime with DeSantis–UPDATED

Sept. 21, 2021 by David Silverberg

UPDATED Sept. 22, 2021 with new information about campaign contribution offer.

Southwest Florida’s lawyers have been busy on the political front this month.

In the case of Casey Askar versus Rep. Byron Donalds (R-19-Fla.), there having been no resolution of the case, a jury trial is scheduled for 9:00 am, next May 18.

To recap: This is a case of defamation and libel. Casey Askar was a Republican primary candidate for Congress last year, running against Donalds, who ultimately won the race.

On primary election day, Aug. 18, a text message was sent to Republicans, allegedly from Donalds, saying that he had dropped out of the race. Donalds vehemently denied its authenticity and accused Askar of sending the false message.

However, Donalds provided no evidence and Askar denied the charge. On Nov. 16, 2020, Askar sued Donalds for defamation and libel, demanding $30,000 in damages.

Since then, the two parties’ lawyers have been wrangling, fighting over the legitimacy of the case, the timing, whether to sit for in-person depositions and the like. Askar is represented by Michael Lawhon of Naples, Donalds by Alan Perlman of Fort Lauderdale.

The next action is scheduled for this Thursday, Sept. 23, when Judge Elizabeth Krier of the 20th Judicial Circuit is scheduled to hear motions to compel Donalds to answer questions and for Askar to file an additional complaint.

While many lawsuits are settled well before they come to trial—sometimes right on the courthouse steps—this one may be different. Whoever sent the original text message committed a federal crime. Askar’s lawsuit is at least partially defensive, since if he wins before a jury he would conclusively prove his innocence.

Unless the case is resolved before its assigned date, Southwest Florida will be treated to a Collier County jury trial in the Spring, just as Donalds’ 2022 re-election campaign ramps up.

It should provide quite the Springtime spectacle.

Oakes, Boatman and DeSantis

Ever since the 2020 presidential election and Donald Trump’s Big Lie that he won in a landslide and it was stolen from him, Trumpers of varying credibility have been insisting that they have the evidence confirming Trump’s delusions.

The most prominent of these folks outside the immediate Trump orbit has been MyPillow chief executive Mike Lindell. He has famously insisted he has compelling proof of the fraud that robbed Trump of another term.

To date, despite much hoopla, Lindell has made no case, sliding down the credibility scale into the laughable range and becoming a late-night punch line.

But in Southwest Florida Francis Alfred “Alfie” Oakes III has stubbornly promoted Trump’s alleged victory since the very day Trump lost. Of course, in January he sponsored two buses of demonstrators to the “Stop the Steal” rally and participated himself.

Now comes Oakes in the form of a Sept. 16 letter by him and James Boatman, managing shareholder of the Naples law firm Boatman Ricci, to Gov. Ron DeSantis (R).

“I am writing today to strongly encourage you to meet with Alfie Oakes and the forensic data experts he wants to bring with him to discuss the verifiable evidence of election fraud that occurred in Florida during the 2020 Election,” Boatman states in the letter, which was released on Sept. 16. “The data doesn’t lie.”

Remember that this was an election of which DeSantis himself said: “The way Florida did it, I think inspires confidence, I think that’s how elections should be run. We’re one of the few states in the country where you can follow the number of people that are voting in real-time. The rest of these states, it’s kind of like a black hole.”

Clearly, Oakes and Boatman don’t agree. “If we do not draw a line on the battlefield on this issue, the Republic will be unrecoverable, as it is nearly lost already,” warns the letter.

Oakes and Boatman want two hours of face time with the governor. In its later paragraphs, the letter starts pleading: “Just show up with an open-mind. What’s the worst thing that could happen?” Possibly, they write, DeSantis would hear nothing compelling. At best, he’d learn something new “which allows you to take action that could change the course of history for this Country and, in fact, for the World.”

In addition to his opportunity to change history, Oakes sweetened the pot for DeSantis by pledging a $100,000 donation to the governor’s re-election campaign if he would meet, according to Jacob Ogles, reporting in Florida Politics. He made the offer during an appearance on Alex Jones’ notoriously extreme Internet program, InfoWars.


The letter concludes: “We are on the edge of an abyss, if not neck deep in one already”—a badly crafted metaphor given that when you’re neck-deep in an abyss you’re no longer on the edge.

Two hours of face time with a governor is a very long time for a very busy man and the discussion may not stay on topic. DeSantis already did a great boon to Oakes last September when he canceled all COVID mandate-violation fines throughout the state. Now Oakes is facing federal pressure to protect his workforce from a virus whose reality he doesn’t admit in order to keep his considerable federal income; perhaps the discussion would also veer into that.

Also unmentioned in the letter is whether this discussion would have to take place in public under Florida’s Sunshine Law.

There are no publicly available indications at this point that DeSantis or his office has received the letter, acknowledged it or responded.

Liberty lives in light

© 2021 by David Silverberg


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