Tickets sell out for local Democratic club event with David Jolly, Josh Weil

The Largo Mid-Pinellas Democratic Club is hosting a general membership dinner featuring former U.S. Rep. David Jolly and former candidate for Florida’s 6th Congressional District, Josh Weil.

The event, at 6 p.m. Monday at the Banquet Masters on 49th Street and Ulmerton in Clearwater, has already sold out.

While Weil offers his own draw — he took on now-U.S. Rep. Randy Fine in a Special Session this year, far outperforming President Donald Trump in the district — it’s likely that Jolly, a rumored Democratic candidate for Governor, is prompting the most intrigue.

More than 200 attendees have been confirmed to a club meeting that has at times struggled to draw a crowd.

“As our membership continues to grow, so does our commitment to bringing relevant, bold, and thought-provoking voices to the forefront,” Largo Mid-Pinellas Democratic Club President Karl Cieslak said. “This event reflects our belief that honest dialogue and community-driven action are the key to a more just and equitable Florida.”

Jolly was a Republican until 2018, when he left the GOP and became an independent. This April, he registered as a Democrat, a completed party swap that follows plenty of speculation that Jolly might run for Governor as a Democrat.

And the writing is clearly on the wall. Jolly has launched a political committee, Florida 2026. He also created a new website whose list of priority issues reads like a campaign platform. And later this week, Jolly is speaking at an event with a minimum $100 contribution to attend, according to an event flyer.

Jolly’s potential bid for Governor has excited some Democrats who view a Republican convert whose ideology fits neatly into the moderate category as the party’s best chance at reclaiming the Governor’s mansion. For this group, Jolly presents an opportunity to tap into conservative voters disenchanted with Trump and his MAGA brand in a state that now heavily favors Republicans.

But the rumors have also frustrated some within the Democratic Party, particularly progressives who worry the state has seen this movie before.

Charlie Crist, who defeated Jolly in 2016 for his congressional seat, was a former Republican Governor when he sought a return to the office in 2022, only to lose as a Democrat by an embarrassing 19 points to Gov. Ron DeSantis. Critics don’t see Jolly as particularly loyal to the party and, as they did with Crist, some have begun to label Jolly an opportunist.

But Jolly has been marching toward the left for several years. Jolly has spent the past decade criticizing extremist policies, and Trump in particular. He’s been a known ally to Democrats, even if he didn’t make his allegiance to the party official until this week. He was a welcomed voice on MSNBC, the broadcast haven for leftists looking to channel their outrage.

In addition to MSNBC, he has also provided largely anti-Trump commentary for Time, USA Today, Roll Call, The Washington Post, The New York Times, CNN, NBC and the Tampa Bay Times.

With Weil in attendance alongside Jolly, it’s likely members will have an opportunity to hear from both about their hopes for the Democratic Party in the Trump era, and at a time when GOP politics dominate Florida.

Weil’s loss to Fine earlier this year was narrow by comparison to Trump’s victory in the district, at just 14 points rather than the 30-point advantage Trump pulled. That’s a possible indication that Trump’s tumultuous second term has soured some conservative voters.

But Jolly will likely also face questions about how he carves a path to victory if other moderate alternatives share the General Election ballot.

State Sen. Jason Pizzo dumped the Democratic Party in an impassioned speech in the waning hours of this year’s Legislative Session, declaring in his remarks that the party was dead. Now, Pizzo says he’ll run for Governor as an independent. Lawyer John Morgan has also publicly mulled a run for Governor, under an as-yet-to-be-announced new political party that would cater to those “stuck in the middle.”

If either of them — or both of them — run, it could end in a situation where candidates are splitting the moderate vote. That would likely hand the keys to the Governor’s mansion to whomever winds up being the GOP nominee, likely U.S. Rep. Byron Donalds.

The club event, in addition to remarks from Jolly and Weil, also includes dinner and opportunities for attendees to get involved in legislative advocacy, upcoming volunteer efforts and local and state organizing.