Trump and Biden land today in Hillsborough, the Florida bellwether that swung left. Can it swing back?

The presidential contenders will hold dueling rallies in Tampa. While Florida and the nation hang in the balance, has the battle for Hillsborough County already been decided?
Trump and Biden cookies are among the bakery items available for sale on Tuesday, Oct. 20, 2020, at Alessi Bakery, 2909 W Cypress St, in Tampa. The bakery is continuing with their annual tradition of selling election cookies with the faces of the candidates. So far, the Trump cookies are outselling Biden cookies.
Trump and Biden cookies are among the bakery items available for sale on Tuesday, Oct. 20, 2020, at Alessi Bakery, 2909 W Cypress St, in Tampa. The bakery is continuing with their annual tradition of selling election cookies with the faces of the candidates. So far, the Trump cookies are outselling Biden cookies. [ DOUGLAS R. CLIFFORD | Times ]
Published Oct. 29, 2020|Updated Oct. 29, 2020

President Donald Trump and former Vice President Joe Biden will land in Tampa today within hours of each other for dueling rallies, putting a spotlight on Hillsborough County just days before the nation picks its next leader.

Trump supporters will gather in the parking lots outside of Raymond James Stadium to hear the Republican president in the early afternoon. Biden, the Democratic nominee, will hold an evening drive-in event at the Florida State Fairgrounds.

In the past, presidential candidates touched down in Tampa hoping to swing the county that swings the swing state. Hillsborough voters picked the eventual president in all but one election from 1960 to 2012.

But the streak was broken in 2016. Democrat Hillary Clinton won Hillsborough by nearly 7 percentage points. Trump won Florida and the White House. And as the presidential campaign turns to Hillsborough once again, many local Republicans, for the first time in a generation, don’t believe the county is even in play.

“Democrats have a lot more momentum,” said April Schiff, the Republican State Committeewoman-elect for Hillsborough. “I think we’re going to see the same thing this time: Trump may take Florida, but definitely not Hillsborough."

Clinton’s victory in Hillsborough was so decisive and announced so early on Election Night that some national pundits familiar with the county’s track record for choosing winners, assumed Florida would fall next and Clinton would coast to the White House. That didn’t happen.

Instead, it signaled Hillsborough was moving further left than Florida. The ensuing years have confirmed it. Democrats, a 5-2 minority on the county commission for much of the last two decades, have since taken control of four of seven seats. They have won an expensive race for a Tampa state Senate seat and flipped an east Hillsborough state house seat long held by Republicans. The county voted for Andrew Gillum for governor in 2018 by an even wider margin than it went for Clinton.

Driving this is a perfect storm of demographic changes favorable to Democrats. Tampa’s downtown, once a desert after 6 p.m., is now full of nightlife, high-rises and millenials. Only Orlando has seen bigger growth in its Puerto Rican population. About 75 people a day move to Hillsborough, including many young families buying homes in booming east county.

“It makes your head spin as quickly as it has happened,” said Shawn Harrison, a former Republican state representative from Tampa.

Harrison would know. His north Tampa district was the definition of a swing seat. He lost it in 2012 by 700 votes, won it back in 2014 and held it by a hair in 2016. Then, two years ago, Democrat Fentrice Driskell, a political newcomer, defeated Harrison by 5,000 votes. This year, Driskell ran unopposed.

“If we don’t change we will become irrelevant in 10 years,” Harrison said. “Less than that probably.”

Democrats see an opportunity to run up the score in Hillsborough, an idea that seemed unthinkable not long ago, when the county overwhelmingly voted to reelect George W. Bush. Ione Townsend, chairwoman of the Hillsborough County Democrats, says the concern with the upcoming presidential election isn’t with their voters, but with the disappointing turnout in South Florida during the past two statewide elections.

“We can’t carry 80 percent of the state,” Townsend said. “So Miami-Dade, Broward and Palm Beach need to take care of their backyard. I hope that Hillsborough County has shown the way and I have every confidence they’ll perform better than 2018, but it may take a couple cycles to get to where they need to be.”

The fast decline of the Republican Party here has led to finger pointing, with many blaming its county chairman Jim Waurishuk. Since taking over the Hillsborough GOP, Waurishuk has narrowed the local party’s focus to supporting Trump. The organization can quickly mobilize Republicans to wave flags whenever the president is in town, but it has done less to boost local candidates. Over the past two years, the local Democratic Party has outraised their Republican counterpart four to one.

Out of frustration, Republicans, including former county commissioner Victor Crist, have considered forming a new political action committee that would usurp the Republican Party of Hillsborough County.

Waurishuk brushed off the criticism and he said he has the ear of those in the Republican Party that matter, including Trump’s inner circle. Waurishuk has been invited to the White House on multiple occasions and met with Trump’s team in Tampa to strategize for the 2020 election. He said the Trump campaign identified Hillsborough early as a critical battleground in the reelection fight where they can erase the deficit from four years ago.

Tampa, which saw $52 million in campaign ads through mid-October, is one of the few markets in the country where Trump is outspending Biden in the closing days of the race, according to a New York Times analysis.

“I’m seeing some favorable numbers,” Waurishuk recently told the Tampa Bay Times. “We’re seeing a lot of Democrats switching parties.”

Trump supporters driving to Raymond James Stadium will see plenty of visual reminders of the president’s popularity with his base. They may catch a glimpse of the massive “TRUMP 2020” flag that flies at the edge of downtown Tampa off Interstate 275 — a declaration to those who speed by that they are entering Trump country.

Early voting in Hillsborough, though, has favored Democrats, who were up by 48,000 as of Wednesday morning. And while Republicans statewide surpassed Democrats in voter registration this cycle, Hillsborough Democrats extended their advantage to 74,000.

Crist said the high turnout clouds which way the race will fall, but he said he sees candidates of both parties running as independents and not partisans. For Republicans, that may signal concern that the president is polarizing in this part of the state. For example, State Rep. Jackie Toledo, a Tampa Republican in a tight fight to hold her seat, recently sent a campaign flier to voters telling them: “Don’t be distracted by national politics.”

“In most of the races right now in Hillsborough,” Crist said, “you can’t tell who is the Republican and who is the Democrat.”

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