Which Hillsborough County will show up on Election Day?

Tomorrow marks the end of two expensive — and contentious — constitutional amendment campaigns.

In a remarkably brief span of time, from 2018 to 2022, Hillsborough County went from a solidly blue county to one that looked strikingly red.

In 2018, Hillsborough voters flipped two Hillsborough state House seats, a state Senate seat, and two County Commission seats from Republican to Democratic, giving Democrats their first Commission majority since 2004. They also went solidly for Andrew Gillum for Governor and Bill Nelson for Senator, even as both lost narrowly statewide.

In 2020, Joe Biden beat Donald Trump 53-46% in the county, even as he lost the state. Democrats won three County Commissioner races, expanding their majority to 5-2, and won every countywide race except Sheriff’s.

Some Republicans despaired over ever winning another countywide race.

But 2022 saw a complete reversal.

Two comparatively unknown Republicans, Josh Wostal and Donna Cameron Cepeda, unseated sitting Democrats and flipped the board majority. Republicans comfortably won the county for Governor, Senator, all statewide offices, and every seriously contested state legislative race.

A big question for Tuesday is which Hillsborough County will appear at the polls: The blue 2018-20 county or the red 2022 one?

County Republican Party Chair Carmen Edmonds said Hillsborough isn’t going back.

“The people who will show up on Tuesday will be the Republicans from 2022,” she said. “What we’re seeing at early voting sites is excitement, a ton of enthusiasm for Pres. Trump. People are wanting change.”

Democratic Chair Ione Townsend didn’t predict a return to 2018, noting that Democrats that year had a big voter registration advantage of about 65,000, or 39% to Republicans 31%. Today, their lead is only about 5,000 votes, 35-34%.

“It’s going to be very close, and Republicans may outvote us, but I think the (no-party registrants) will break our way,” she said.

Democratic voter turnout collapsed in the 2022 Election, down to 52% compared to 2020’s 78%.

On Tuesday, “Turnout will be helped with Kamala Harris at the top of the ticket — there’s a great deal of enthusiasm about her,” as well as the abortion rights and recreational marijuana amendments and Senate candidate Debbie Mucarsel-Powell, Townsend said.

Townsend and other Democrats have cited a wave of Democratic volunteers who showed up after Harris replaced President Joe Biden at the top of the ticket.

Others note that the county’s total active voter numbers have dropped substantially despite an increase in population, with nearly all the losses among Democrats. Many of those voters may have been listed as inactive, having missed two straight elections, but some could still show up and vote on Tuesday.

The answer could affect these top Hillsborough races on Tuesday:

— Suzy Lopez vs. Andrew Warren, State Attorney

For Democrats, this is a grudge match, and it’s also one where the prestige of Gov. Ron DeSantis is on the line.

In 2022, DeSantis removed Warren from the State Attorney’s Office, to which he’d been elected twice, replacing him with Lopez after citing Warren’s statements on reluctance to enforce laws criminalizing abortion. DeSantis later boasted as a presidential candidate about removing a progressive prosecutor and also removed another, Monique Worrell of Orlando.

Warren, meanwhile, became a hero to local Democrats, getting standing ovations at gatherings of party insiders, and sued to overturn his removal. A federal judge ruled DeSantis acted illegally but declined to reinstate Warren; Warren is appealing against that decision.

Lopez has substantial support, particularly from police unions, and has raised $1.2 million to Warren’s $762,379.

If Warren wins, it’s unclear whether DeSantis will try to remove him again.

— Chris Boles v. Sean Shaw, countywide County Commissioner

Democrats have seen their previous 5-2 majority on the Board of Commissioners collapse to a 3-4 minority and must win this race, replacing term-limited Democratic Commissioner Pat Kemp, just to hold their current numbers.

Boles is a first-time candidate for office but benefits substantially from his status as treasurer of the politically active local firefighters union, a chapter of the International Association of Firefighters.

Shaw, long prominent among local Democrats, is a lawyer, former state House member and former candidate for state attorney general, also known as the son of the late Leander Shaw, the first Black chief justice of the state Supreme Court.

— School tax referendum.

According to school officials, Hillsborough public schools face a severe teacher shortage and are losing teachers to surrounding counties that have extra property taxes to support salaries.

As a result, the county school board fought through a political controversy to put a referendum on the ballot for a tax of 1 mill, or $1 per $1,000 worth of assessed property value. School officials say that the tax would raise $177 million a year for four years, 92% of which would be devoted to teachers’ salaries.

The four Republican County Commissioners, led by Wostal, tried to keep the tax off the ballot. The real estate development industry has led a campaign against it, including mailers and digital advertising.

A similar measure failed by a razor-thin margin in 2022.

— Community Investment Tax

The county’s Community Investment Tax, a half-percent sales tax, is devoted to infrastructure projects, including roads, fire stations, stormwater and utility projects, and equipment, including fire and rescue and police vehicles.

Voters approved it for 30 years in 1996, and it expires in 2026. County and city officials say renewal is badly needed, and the money would be shared with municipalities.

The renewed tax is estimated to raise $201-$214 million in each of its first two years.

Unlike the original version of the tax, which devoted 25% of the revenue to school construction, only 5% of the renewed tax would go to schools. A substantial amount would continue to go to sports facilities, including Amalie Arena, Raymond James Stadium, and Steinbrenner Field, for maintenance and repairs.

— Ashley Brundage vs. Karen Gonzalez Pittman, state House

Republican state Rep. Gonzalez Pittman looks like a good prospect for re-election, but the state Republican Party is campaigning as if she faces a threat from a comparatively unknown, first-time candidate, Democrat Ashley Brundage.

Democrats have targeted the seat as one of eight statewide, hoping to flip a red seat to a blue one. Five flips would end the Republican Party supermajority in the House.

The state Republican Party won’t say how much it has spent on the race, but it is clearly well into six figures judging from the onslaught of mailers — at least 17 in the last two weeks, at a likely cost of five figures each — plus TV and digital advertising.

Pittman is the wife and co-owner of her physician husband’s vein care practice. Brundage is a diversity consultant and former banker who would be the Legislature’s first transgender member.

The South Tampa-to-Westchase district has a 39-30 percent Republican-Democrat registration advantage, and Pittman won it by almost 8 points in 2022 against a strong challenge from Democrat Jen McDonald.

Pittman has raised more than twice as much as Brundage, $420,567 to $177,770, not including the party spending.

— Constitutional officers

Three Hillsborough Democratic constitutional officers face GOP opponents, while Republican Sheriff Chad Chronister and Democratic Tax Collector Nancy Millan are unopposed.

Townsend said she’s confident of the three Democrats’ wins — Property Appraiser Bob Henriquez, Elections Supervisor Craig Latimer, and Clerk of Court Cindy Stuart—but Edmonds said she believes her party’s candidates will be competitive.

Stuart faces the best-known challenger, former state senator and longtime university-area community activist Victor Crist.

Karen Bendorf vs. Lynn Gray, School Board

Like many recent school board races, this non-partisan race has taken on partisan overtones.

Bendorf, a Plant City Republican and middle school teacher, has said she was motivated to run partly because she opposes the board’s advocacy of a tax increase for teachers’ salaries and stances it has taken in proclamations, including one celebrating Pride Month.

Gray, a Democrat, is a former longtime teacher now finishing her second term on the board. She favored the tax proposal.

Kathy Castor vs. Rocky Rochford, U.S. House.

Robert “Rocky” Rochford is the latest of a long line of Republicans to challenge U.S. Rep. Castor, now completing her ninth term in Congress from Tampa.

Rochford is a retired Navy officer whose campaign emphasizes closing the southern border to immigrants, who he says threaten the nation’s security and the economy, which he says is “a disaster.”

But he faces an uphill battle at best.

In 2022, DeSantis pushed through the state Legislature a redrawn map of congressional districts that aimed to concentrate as many Democrats as possible into Castor’s district, paving the way for Republicans to win the surrounding districts. The new map extended the district across the bay to take in heavily Democratic parts of St. Petersburg.

Even before that, the district was heavily Democratic. Until James Judge came within 8 points of her in the 2022 red wave, she had never won re-election by less than 20 points.