PINELLAS COUNTY, Fla. — As recently as 2016, Hillsborough County was considered by national political reporters to be one of the most significant battleground counties in the entire country when it comes to deciding the presidency.

POLITICO listed Hillsborough among “25 Battleground Counties to Watch” in August of 2016.  Four years earlier the same publication called the county “one of the nation’s top bellwethers.”

But Hillsborough went decisively for Hillary Clinton in 2016, and followed up in 2018 by supporting two tax increases and voting in two new county commissioners to give Democrats control of that board for the first time in 14 years.  

Now it’s Pinellas County’s moment in the national focus. It was one of only four counties in Florida who voted for Barack Obama in 2008 and 2012, and then shifted to Donald Trump in 2016.

“It’s truly a swing county because it swings with the national mood,” says political strategist Barry Edwards, who has worked in Pinellas County politics for 40 years. “Donald Trump got a Republican wave in ’16. It matched the national swing and they voted for Donald Trump. You had a correction in 18 and it corrected back for the Democrats. “ 

In fact, Pinellas County has voted for the winning presidential candidate in every election since 1976 with just one exception – when it went for Al Gore, who infamously lost to George W. Bush by just 537 votes in Florida in 2000.

But it should be noted that over the past decade - with the exception of Trump in 2016 – the county has usually voted for a Democrat in the top race in the state (including gubernatorial candidates Alex Sink, Charlie Crist and Andrew Gillum). 

There’s no question that winning the county is crucial for Donald Trump’s chances of winning Florida and keeping himself viable for an Electoral College victory.

“Both sides realize that if they can win Pinellas County, that will go a long way in terms of deciding who wins the state of Florida,” says Darryl Paulson, an emeritus professor of government at USF-St. Petersburg. “It really is the jewel in the crown. The most competitive county in the most competitive state in the country.”

Republicans feel good about their chances in the county this year.

“The kind of grassroots organic mobilization in Pinellas has just been amazing to watch,” says Pinellas County Republican Party Chairman Todd Jennings. 

Democrats have boasted that they’re fielding candidates in virtually every race on the ballot this cycle. But with all of the constitutional officers in Pinellas being Republicans, Jennings thinks that could backfire in Pinellas County.

“They’ve thrown somebody up against Nick DiCeglie. They’ve thrown up somebody against Chris Sprowls,” he says, referring to two Pinellas House Republicans who are considered favorites to win their battles for reelection this fall against their Democratic opponents (Patricia Plantamura against DiCeglie in the HD 66 race and Kelly Johnson against Sprowls in HD 65, respectively). “Why would they want to force just about every prominent Republican in the county to turn on their machines and get to work to get re-elected? I think that’s really going to help Republican turnout.”

But Pinellas County Democratic Chair Barbara Scott says that Donald Trump will be a drag on the GOP this fall and thinks Pinellas Republicans are “being a little misguided if they don’t think that’s going to affect the down-ballot.”

“They turned their party over to Donald Trump, and I think it’s going to affect all of them, and I think that they’re being delusional if they’re not paying attention to that,” Scott added.

Equality Florida’s Nadine Smith also believes that Pinellas will go blue this fall. The South St. Pete resident – who is the executive director for the state’s leading LGBTQ-rights group in the state - says the fact that St. Petersburg has become such a progressive hub is significant.

“People who live in close proximity are exposed to more differences,” she says. “They see people not just as caricatures but as real people. Those aren’t immigrants, those are my neighbors, you know. Whatever I thought about gay people, that’s my city council members. It shatters a lot of those fears that stem from lack of contact, lack of exposure, and so the more Florida becomes more urban you see that shift happening more and more.” 

Meanwhile in Hillsborough County, Democratic Party Chair Ione Townsend hopes to continue the Democrats winning streak which has taken place since she became chair in January 2016.

She says one of the things that she did upon taking control was realizing that nearly two-thirds of Hillsborough Democrats lived outside of Tampa, so she reorganized the organization to make it less Tampa-centric, and more focused in eastern Hillsborough communities like Brandon, Riverview and Plant City.

Townsend has also separated the county into seven different regions, where volunteers have been physically dropping candidate literature and slate cards to hundreds of thousands of Democrats and left-leaning NPA households this cycle.

Jim Waurishuk, the chairman of the Hillsborough County Republican Party, says he believes “there’s a possibility” that Trump can win the county in November.

Waurishuk cites certain metrics, but admits that a certain degree of his optimism is anecdotal. He says that the party is seeing a considerable amount of Democrats who say they have concerns about security and say they’re going to vote for the president. “We’re hearing that from the Trump campaign. We’re hearing it from Black Voices for Trump. We’re hearing that from Latinos for Trump,” he says. 

Waurishuk also says that when he meets with Hillsborough Republican voters to encourage them to support candidates running for county commission and other local offices, the one question he most frequently gets is simply: “Are they supporting Trump?”