Politics
[Opinion] The Barbs Are Flying in the Florida State House District #44 Special Election
ORANGE COUNTY, Fla. (FNN NEWS) – A special election for the Florida State House District 44 seat is on the immediate horizon to replace recently appointed 5th District of Appeals Judge Eric Eisnaugle. Interestingly, the outgoing Eisnaugle won his original election to the District #44 seat in–you guessed it–a special election, in 2014. Eisnaugle high-handedly beat out Democrat Sean Raja in a district that skews heavily Republican. But this special election has opponents and supporters already swinging for this highly sought-after seat with roughly two months remaining before the primary.
Photo courtesy of 5th District of Appeals Judge Eric Eisnaugle (pictured).
Florida Governor Rick Scott announced the primary for the special election will be on August 15th and the special election for the Florida House District 44 seat will be October 10th. Running for the seat are five candidates that qualified in mid June: one Democrat and four Republicans. The predominantly white District has approximately 112,000 registered voters, with Republicans leading the pack. The easiest description of the district is West Orange County, but it’s basically bordered from Osceola County to Apopka including the heavy voter turnout areas of Dr. Phillips, Bay Hill and Windermere, up to parts of Winter Garden.
Let me briefly break down each candidate.
PAUL CHANDLER: THE SOLE DEMOCRAT TO QUALIFY IN THE RACE
Florida House District 44 Democratic candidate Paul Chandler. Photo courtesy of Yahoo Images.
Democrat Paul Chandler automatically goes to the special election in October because he is the only Democrat that qualified by deadline. Chandler is founder, president and chairman of Ohana Healthcare, a multi-state company he runs from offices near Lake Buena Vista that provides full-service operational services and education programs to small-and medium-size physicians groups and small hospitals. I was unable to locate a campaign Facebook or political webpage to share and his campaign finance reports are grim at best.
Photo courtesy of Orange County Democratic Party Chairman Wes Hodge (pictured).
Wes Hodge, Chairman of the Orange County Democratic Party said of Chandler’s chances, “House District 44, much like the rest of Orange County, is trending Democratic as we move forward. The Orange County Democratic Party is glad our voters will have a clear choice in October, and they will be able to vote for a candidate who is willing to represent their ideas in Tallahassee.”
But not so fast there Kemosabe. The numbers make it very difficult for a Democrat to pull off a victory in District 44. Special elections, at best, bring out roughly 10 percent of registered voters, suggesting we’re most likely looking at a race that could be decided with as few as 10,000 total votes. The 2014 special election brought out roughly 9,500 people, mostly Republican voters. Three years later, and with this race gaining a great deal of attention, a number like 10,000 is a safe bet in a district that traditionally over-performs in voter turnout. Eisnaugle, the Republican, overwhelmingly won in 2014 with roughly 7,000 votes.
Moving onto the Republicans in the order of who will most likely deliver votes (from least to most likely). Chadwick Hardee, Vice Chairman of the Orange County Republican Executive Committee had this to say: “It is good to have great community leaders that are qualified to run. Whoever wins is set up to potentially make a run at House Speaker, and that’s exciting.”
Photo courtesy of Orange County Republican Executive Committee Vice Chair Chadwick Hardee (pictured).
Let’s meet the Republican candidates.
DR. USHA JAIN
Photo courtesy of Dr. Usha Jain (pictured).
Dr. Usha Jain is a medial doctor and former candidate for Orange County Commission. Dr. Jain seems to have her heart in the right place, but lacks the basic fundamentals of a viable campaign. Her messaging and campaign structure are bare and her ability to raise funds, based off of her filed campaign reports, is less than impressive. Dr. Usha Jain, “I am from India and I’m also Hindu with Jain religion which is purley based on nonviolence and karma. Dr. Jain is a vegetarian and believes in nonviolence and karma.”
ONE TO WATCH: BRUNO PORTILIATTI
Photo courtesy of Bruno Portiliatti (pictured).
Portiliatti is CEO (Chief Executive Officer) at Excellence ALF. A quick review of his Facebook page suggests that he’s relatively young and newly married. Portiliatti has a professional appeal and produced a well articulated campaign video. With over 16,000 views at the time this article, certainly people are paying attention to this relative newcomer in Orange County politics. He is probably not a contender in this particular race, but he could simply be testing the waters for reaction and a future run in another race.
Now we come to the players in the race, Bobby Olszewski (Bobby O) and John Newstreet. When “Bobby O” entered the race in April it was no surprise. With rumors swirling about the possibility of Eisnaugle being appointed to the appellate court, the political players started aligning themselves to take a run for the anticipated open seat. Let’s quickly recap both contenders and then briefly dive into the waters starting to become a bit murky in the House #44 race.
JOHN NEWSTREET
Photo courtesy of John Newstreet (pictured).
Who?
When I first heard the name John Newstreet I immediately had to look him up. But my lack of knowledge was quickly shadowed by the deluge of support he garnered almost immediately, raising nearly $80,000 right out of the gate. Newstreet, a military Veteran, comes from a large family that embraced adoption in increasing their family tree. Newstreet recently moved into the district, but has a long history of working behind the scenes in politics, dating back to his days at the University of Central Florida. Additionally, he just received the endorsement of The West Orange Political Alliance.
Photo courtesy of Jacob Engels, founder of Central Florida Post (pictured).
Further discussions during my interview with Jacob Engel, founder of the Central Florida Post, suggest Newstreet has far deeper roots than most realize. He also appears to have some heavy-hitting support in Orange County Commissioner Scott Boyd and rumor has it he’s hired well known political consultant John Dowless to lead his campaign. Not shabby for a newcomer. But as we all know, money is nice, but name recognition has substantial value, so don’t be surprised if we start seeing a heavy push by the Newstreet camp to increase his name and brand recognition in West Orange County. In fact, it must be his priority or he’ll fail to be a contender for the seat. No denying he’s certainly off to a great start. His campaign page can be found here.
BOBBY “O” OLSZEWSKI
Photo courtesy of Bobby Olszewski (pictured).
Olszewski, a new father and well known political stakeholder in West Orange County, is a former Winter Garden Commissioner who resigned to run for Orange County Commissioner in 2016 in a narrow loss to Betsy VanderLey. Olszewski also has a number of well known public figures that have endorsed his candidacy. He is known for a substantial ground game and grassroots approach to campaigning. In recent weeks, however, he has faced harsh criticism for his engagement in what Engels refers to as a “scam to defraud taxpayers.” In its simplest form, it appears Olszewski was involved in the development of a for profit company, via the support of Apopka Mayor Joe Kilsheimer and Florida State Senator Randolph Bracy, that helps felons restore their rights. (More background on this detailed here.) However, I have spoken to Bobby “O” and he adamantly denies any wrongdoing and feels the effort to discredit him is a veiled attempt to help the establishment choice in Newstreet.
NO BROMANCE HERE
Photo courtesy of Orange County Commissioner Scott Boyd (pictured).
Chiming in on this race is outgoing two-term Orange County Commissioner Scott Boyd. The relatively under-the-radar commissioner has been posting some harsh criticism of Olszewski on his Facebook page.
“The only thing this guy stands for is himself. I personally picked up his slack to the tune of nearly $5,000 for a couple of back to school events he failed to provide for. Now he wants $500,000 of our tax dollars to start a bogus private felony rehab program for a community he couldn’t even pull together a few hundred back packs [for].”
When I first read his Facebook post I had to read it again, as I have rarely seen the Commissioner speak in a negative way. However, this is an ongoing feud between Boyd and Olszewski since Olszewski’s bid to replace Boyd in the Orange County District 1 Commission race.
Boyd continued with another post, “Will the former Winter Garden Commissioner and failed Orange County Commission candidate now House District 44 candidate disclose his finance report? In the Orange County Commission election he ran all of the expenses through a personal credit card. Last I checked 1.5 miles in sky miles for every dollar spent would be a nice bonus for the candidate.” Needless to say, there appears to be some bad blood flowing.
So with that challenging optic, can Olszewski win? The answer might very well rest in how he handles the next two months of campaigning as whichever Republican comes out of the primary victoriously will most likely win the State House 44 race and possibly be in line to be the next House Speaker. And folks…that’s power squared.
HOW A SPECIAL ELECTION DIFFERS FROM A TRADITIONAL ONE
It’s important to remember how special elections are different than a traditional election. For example, in a Presidential election cycle, people feel an obligation to make their way to the polls–a patriotic duty, if you will. Even off-year gubernatorial elections draw traditional voters. But a special election is much more personal. Outside of the loyal party base on both sides, since only Democrats or Republicans can vote in a primary (and in this case only Republicans will be voting since there is only one Democrat), votes really are driven by allegiance to a candidate. This is where Olszewski has the upper hand as it’s no secret he has a substantial base of support in West Orange County, having just completed a huge push in 2016 for the County Commission seat. But will the base come out again? Can he hold on to his healthy list of endorsements? Only time will tell.
I’ve failed to find anyone who will deny Bobby “O” is not one of the hardest working politicians in Orange County. He will do the work of knocking on doors and will reintroduce himself to his community bar none. However, you can count on Newstreet, and possibly the other candidates, looking to use Olszewski’s recent perceived missteps on mailers and in social media blasts. One source suggests, “don’t believe a thing he says. He’s a liar.”
Ouch! Well, I only know Olszewski through politics, but he has always been respectful and pleasant. But one thing anyone in politics knows … it’s all about mending fences and building bridges. And this negative imaging, true or not, does require some cleanup work even if Olszewski wins. All in all, it’s Olszewski’s race to lose. He knows how to work the ground game and he knows how to excite his base. But can he put the edgy personality aside long enough to get through the primary? Engels said, “I like Bobby. But he has a big personality that might be a hard pill to swallow for donors and supporters.”
Well, two months is a lifetime in politics and Newstreet, even for No Party Affiliation (NPA) voters and Libertarians I’ve talked with, gets the nod on being the most grounded and articulate in a public forum.
The special election primary is in August followed by the special election October 10th. All candidates are campaigning for a job that pays a whopping $29,697.00 annually–a $30k/year job that, upon election, pretty much requires 24/7 fundraising until the next election; excluding the time that the legislature is in session.
All candidates have met the requirements of being 21 years of age, have lived in Florida for two years and live in the District they intend to serve.
Stay tuned for more follow-up and one-on-one interviews with candidates in this race willing to state their case to the voters.
Here we thought the Orlando City Council District 5 race would be the only dramatic political race to watch. Looks like we now have two reality shows to watch this season. Grab your popcorn everyone…
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Randy Ross is a political reporter for Florida National News | info@floridanationalnews.com
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Politics
Eight Black Major-Party Gubernatorial Nominees Head to November Ballot in Historic 2026 Election
Five Democrats and three Republicans are competing across eight states, a remarkable milestone in a nation that has elected only three Black governors
WASHINGTON (FNN) — Eight Black major-party nominees are running for governor across the United States in the 2026 general election, creating an unprecedented moment in American gubernatorial politics.
The field spans both major parties and eight states: Florida, Georgia, Maryland, Michigan, Minnesota, Nevada, South Carolina and Wisconsin. Five nominees are Democrats and three are Republicans. Seven are seeking to become the first Black governor elected in their respective states, while Maryland Gov. Wes Moore is seeking reelection.
The number is particularly striking because only three Black Americans have ever been elected governor: Douglas Wilder of Virginia, Deval Patrick of Massachusetts and Moore of Maryland. All three are Democrats and men.
That means more than twice as many Black major-party gubernatorial nominees are competing in 2026 alone as the total number of Black Americans ever elected governor.
Eight Black major-party nominees are running for governor across eight states in the November 2026 general election: Keisha Lance Bottoms (D-Georgia), David Crowley (D-Wisconsin), Byron Donalds (R-Florida), Lisa Demuth (R-Minnesota), Aaron Ford (D-Nevada), John James (R-Michigan), Jermaine Johnson (D-South Carolina) and Wes Moore (D-Maryland). Moore is seeking reelection, while the other seven could become the first Black governors elected in their respective states. Source Florida National News (FNN)
Why It Matters: Eight Nominees, Only Three Black Governors Elected
Governors occupy some of the most powerful elected positions in American government, overseeing state agencies and budgets while exercising authority over legislation, appointments and executive policy.
Yet Black representation in governors’ mansions has remained exceptionally rare.
Wilder became the nation’s first elected Black governor when Virginia voters elected him in 1989. Patrick followed in Massachusetts in 2006. Moore became the third with his Maryland victory in 2022. Moore is currently the nation’s only Black governor.
The 2026 field could significantly expand that history — and potentially establish several additional firsts.
Either Keisha Lance Bottoms or Lisa Demuth could become the first Black woman elected governor in U.S. history. Republican nominees Byron Donalds, John James and Demuth also represent the possibility of another gubernatorial milestone.
But the candidates do not represent a single political movement. Their backgrounds, ideologies and policy positions differ substantially.
That distinction is central to understanding the significance of 2026: Black representation at the gubernatorial level is appearing across party and ideological lines.
Meet the Eight Black Major-Party Nominees
Byron Donalds — Florida — Republican
Former U.S. Rep. Byron Donalds won Florida’s Republican gubernatorial nomination Aug. 18 and is seeking to succeed term-limited Gov. Ron DeSantis.
Donalds previously served in the Florida House before his election to Congress representing Southwest Florida. A prominent conservative and ally of President Donald Trump, Donalds faces Democratic nominee and former Republican U.S. Rep. David Jolly in November. Florida election records confirm the Donalds-Jolly general-election matchup.
If elected, Donalds would become Florida’s first Black governor.
Wes Moore — Maryland — Democrat
Wes Moore is the only incumbent governor among the eight nominees.
An Army veteran, Rhodes Scholar, author and former nonprofit executive, Moore was elected in 2022, becoming Maryland’s first Black governor and only the third Black American elected governor of any state.
He is seeking a second term.
Keisha Lance Bottoms — Georgia — Democrat
Former Atlanta Mayor Keisha Lance Bottoms is the Democratic nominee in Georgia.
Bottoms served as Atlanta mayor from 2018 to 2022 and later served in President Joe Biden’s administration. She faces Republican Rick Jackson in November.
A Bottoms victory would make her Georgia’s first Black governor and could make her the nation’s first Black woman elected governor.
John James — Michigan — Republican
John James, a businessman, Army veteran and former member of Congress, is Michigan’s Republican gubernatorial nominee.
James previously mounted two campaigns for the U.S. Senate before winning election to the U.S. House in 2022. He faces Democratic nominee Jocelyn Benson in November.
A James victory would make him Michigan’s first Black governor.
Lisa Demuth — Minnesota — Republican
Minnesota Republican Lisa Demuth entered the 2026 campaign with a history of breaking political barriers in her state.
Demuth, a business owner and state lawmaker, became Minnesota’s first Black House speaker. She defeated a Republican primary field that included MyPillow founder Mike Lindell and now faces Democratic U.S. Sen. Amy Klobuchar in the general election.
If elected, Demuth would become Minnesota’s first Black governor and could become the first Black woman elected governor in U.S. history.
Aaron Ford — Nevada — Democrat
Nevada Attorney General Aaron Ford is the Democratic nominee for governor.
Ford previously served as majority leader of the Nevada Senate and became Nevada’s first Black attorney general. He is challenging incumbent Republican Gov. Joe Lombardo.
A victory would make Ford Nevada’s first Black governor.
David Crowley — Wisconsin — Democrat
David Crowley, the Milwaukee County executive and a former Wisconsin state representative, won the Democratic gubernatorial nomination after a closely contested primary.
Crowley became the first Black person elected Milwaukee County executive in 2020. He faces Republican Tom Tiffany in November.
If elected, Crowley would become Wisconsin’s first Black governor.
Jermaine Johnson — South Carolina — Democrat
South Carolina state Rep. Jermaine Johnson is the Democratic nominee for governor.
Johnson has served in the South Carolina House since 2020 and is seeking the state’s highest executive office.
If elected, Johnson would become South Carolina’s first Black elected governor.
Five Democrats, Three Republicans — And Different Political Visions
The historic nature of the field should not obscure its political diversity.
Democrats: Wes Moore, Keisha Lance Bottoms, Aaron Ford, David Crowley and Jermaine Johnson.
Republicans: Byron Donalds, John James and Lisa Demuth.
The candidates differ on major questions of taxation, abortion, education, voting laws, health care, economic policy and the role of state government.
AP reported that many of the candidates have not made race the centerpiece of their campaigns, instead emphasizing their qualifications, policies and governing priorities.
Their shared place in history therefore should not be interpreted as shared politics.
Florida’s History: Andrew Gillum Came Close in 2018
Florida has faced the possibility of electing its first Black governor before.
In 2018, Tallahassee Mayor Andrew Gillum, a Democrat, faced Republican Ron DeSantis in the general election.
Gillum came remarkably close to making history. DeSantis ultimately prevailed by roughly 32,000 votes out of more than 8 million cast, a margin of less than half a percentage point.
Gillum’s defeat left Florida without a Black governor.
Eight years later, the possibility has returned from the opposite side of the political aisle.
Donalds won the Republican nomination with 811,131 votes, or 47.79%, in the Aug. 18 primary, according to official Florida election results. Jolly captured 60.95% of the Democratic primary vote.
The historical connection between Gillum and Donalds is narrow but significant: they represent different parties, political philosophies and eras, but both became major-party nominees with an opportunity to become Florida’s first Black governor.
2026 Could Produce Several Historic Firsts
The November elections could substantially rewrite the history of Black gubernatorial representation.
Seven nominees could become the first Black governor elected in their states. Bottoms or Demuth could become America’s first Black woman elected governor. Moore could win another term as Maryland’s first Black governor.
The outcomes will ultimately depend on voters evaluating each candidate individually — their records, policies, qualifications and visions for their states.
Historical significance does not determine an election result.
A National Milestone Before November Votes Are Counted
Whatever voters decide, 2026 has already established a milestone.
Eight Black major-party nominees are competing for governor across eight states in the same general-election cycle — more than twice the number of Black Americans who have ever been elected governor.
They are Democrats and Republicans, incumbents and challengers, veterans, lawmakers, executives and attorneys. Their political philosophies differ, sometimes dramatically.
What connects them historically is much narrower — but consequential.
For the first time, American voters in eight states will simultaneously consider Black major-party nominees for governor, putting the possibility of several new chapters in American political history directly in the hands of voters this November.
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