If Republican nominee Bobby Olszewski wasn’t such a prohibitive favorite, the upcoming special election for Florida House District 44 would be filled with intrigue.

The Democrat’s nominee Paul Chandler, is an affable man, a former teacher and a successful businessman with strong backgrounds in education and the intricacies of health care money, two of the Democrats’ platform highlights, and brings a standard progressive Democratic platform.

Yet Chandler’s qualification to run is being challenged in court, and even his own party’s officials aren’t confident he can win there. He’s staying in the race in defiance of their wishes, and might have to campaign without their help, something he’s already written off as something he said he wasn’t expecting at any rate.

And this is a district that not only hasn’t elected a Democrat in memory, it hasn’t even had an actual Democratic nominee in seven years.

“We are still proceeding forward to fight,” Chandler said on Friday.

The southwest Orange County district includes some old-Florida areas, older suburbs such as Ocoee and Oakland, and high-growth, areas such as Olszewski’s hometown of Winter Garden, Windermere, Dr. Phillips, and Hunters Creek.

It also is home to all three of Central Florida’s theme park giants – Walt Disney World, Universal Orlando, and Sea World Orlando, and much of the tourism corridor along International Drive and State Road 535. If there is a Florida House district that is most important to Florida tourism interests, it is HD 44.

Olszewski has plunged forward in his campaign, happy to know who will be his opponent. After winning a bruising primary, he’s shoring up endorsements from influential business groups that had endorsed his main primary opponent, John Newstreet, including the Central Florida Hotel & Lodging Association. He’s raising money, with a big fundraiser set for next week. He’s assembled a savvy, professional campaign staff.

Olszewski is a well-known figure, a former Winter Garden commissioner with deep community roots and broad support from other elected officials in the area. He also has his powerful political enemies, particularly within the Republican Party, due to the anti-cronyism bent he shares with House Speaker Richard Corcoran. But they’re unlikely to rock his boat against a Democrat.

Olszewski also is known as one of the hardest-working campaigners in Central Florida, someone who proudly [and with some exhaustion] says he lost 40 pounds this year walking door-to-door to meet voters. He is unlikely to change that approach, or take Chandler for granted.

Chandler is not without prospects.

First, the district, like all of Orange County, is changing, picking up more blue voters. Once a bastion of Republican voters, it now gives less than a four-point advantage to the GOP. Republican voters make up 36.1 percent of the base, in the last registration book closing, while Democrats make up 32.4 percent, and independents and others 31.5. The district voted for Hillary Clinton over Donald Trump last fall. The southern part of the district has a significant and growing Hispanic population, and the northern part a significant black population.

Chandler is seeking outside backing in lieu of the party, including from the Pride Fund To End Gun Violence, a national group started in reaction to the Pulse massacre in Orlando last year that pours money and effort into races to support candidates who support both LGBTQ rights and gun restrictions, which Chandler, who is openly gay, does.

He contends he has tapped into his own base of eager volunteers and grassroots activists. And he’s pledged to match Olszewski step-for-step in shoe-leather campaigning.

But first he must overcome key challenges and questions.

Will the lawsuit against him, charging that he voted in Missouri last year and is therefore ineligible to become a Florida House member this year, go forward?

There has been no action by the plaintiff, Charles Hart of Windermere, since Aug. 9, the day after it was filed. Neither Hart nor his attorney Roger Beaubien responded to an Orlando-Rising.com inquiry about whether they intend to continue the action.

The suit was assigned to Judge Charles Dodson of Florida’s 2nd Judicial Circuit in Tallahassee on Aug. 10, but he has scheduled nothing.


About The Author

Scott Powers is an Orlando-based political journalist with 30+ years’ experience, mostly at newspapers such as the Orlando Sentinel and the Columbus Dispatch. He covers local, state and federal politics and space news across much of Central Florida. His career earned numerous journalism awards for stories ranging from the Space Shuttle Columbia disaster to presidential elections to misplaced nuclear waste. He and his wife Connie have three grown children. Besides them, he’s into mystery and suspense books and movies, rock, blues, basketball, baseball, writing unpublished novels, and being amused. Email him at scott@floridapolitics.com.

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