Winners & Losers

This week’s biggest Winners & Losers

Who’s up and who’s down in the Sunshine State?

Is Gov. Ron DeSantis a political winner or loser because of the “Air DeSantis” migrant flights to Martha’s Vineyard? No surprise: It depends. For example, Los Angeles Times columnist Michael Hiltzik called it an “infantile stunt” and California Democratic Gov. Gavin Newsom said DeSantis’ flights were “a disgrace … almost monstrous.” Fox News’ Tucker Carlson counters by saying, “We're being invaded and now they're talking about prosecuting Ron DeSantis because he sent 50 people to Martha's Vineyard who were immediately deported so they wouldn't get in the way of the Food and Wine Festival?” See how hard this is? Now on to this week’s Winners & Losers.

WINNERS:

Terry Gwinn -

This Suwannee County farmer isn’t just a winner because he scored the first new medical marijuana license from the state in years. Terry Gwinn also is a winner because that license is more golden than a Willy Wonka ticket. As the News Service of Florida’s Dara Kam recently pointed out, existing licenses “have sold for more than $50 million.” Ka-ching! Of course, nothing will happen right away as the losers file challenges. Call this a long-term investment – assuming Gwinn emerges legally unscathed.

Dave Kerner -

Many Democrats were left scratching their heads when Palm Beach County Commissioner Dave Kerner endorsed Gov. Ron DeSantis this week. But the endorsement could help secure his positioning in the political maneuvering for the county’s sheriff vacancy in 2024. The long-time Democrat could expect to secure much of the blue county’s Republican voters after the endorsement, meaning he would only need a portion of Democratic support to win the seat in two years. Whatever works!

James Montgomerie -

He’s awash in hundreds of thousands of dollars thanks to Florida’s governor and a group of Venezuelans. CEO James Montgomerie’s Vertol Systems in Destin now has been paid around $1.5 million to relocate migrants. Note that Montgomerie “has contributed exclusively to GOP causes both individually and through his company in Florida,” The Daily Beast reports. And one flight showed up in Delaware, home to President Joe Biden, with no passengers! As Sinatra sang, “Nice work if you can get it, and you can get it if you try.”

LOSERS:

Michael Shirley -

A playing of “Bad Day” is going to hit differently for this former Republican operative and campaign consultant. A former underling of disgraced Seminole County Tax Collector Joel Greenberg, Michael Shirley has just been charged with paying bribes in exchange for favorable treatment from a Seminole County public office. He got $466,625 from his scheme, but now faces four counts of fraud and a charge of conspiracy to commit fraud. He needs to sing a sad song just to turn it around.

Donald Trump -

We try to avoid putting this particular Florida man in the Winners & Losers just because he’s so larger than life that he usually transcends winnerishness and loserdom. We’ll make an exception this week: New York’s attorney general filed a lawsuit alleging “Trump, three of his children, the Trump Organization and others engaged in ten years of financial fraud.” The special master in the Mar-a-Lago raid told his lawyers “you can’t have your cake and eat it too” about protecting documents from review. And the latest poll shows Ron DeSantis leading the ex-president in a hypothetical Florida primary. “Sad” indeed.

Andrew Warren -

Warren’s war with the governor will keep raging after his bid for automatic reinstatement as Hillsborough County’s elected state attorney was denied. While he could run for the office again in 2024, or even win in court eventually, his saga to seek reemployment likely will take several years to play out. Meantime, a reckoning in the Florida Senate – which ultimately decides executive suspensions – is on hold because outgoing President Wilton Simpson said he didn’t want to address the case until it’s played out in court. And so, Warren will wait.

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