San Antonio is barreling toward the most bizarre mayoral election in recent memory.

A massive field of 27 candidates has no clear frontrunners. State and national PAC money is flowing into the race while local groups remain on the sidelines. Meanwhile, the rare opportunity to lead a blue city in a red state has both Republicans and Democrats salivating over the traditionally nonpartisan office.

Weeks from the start of early voting in the May 3 election, it’s the exact scenario some local political strategists say they’ve long worried about leading up to a pivotal race.

San Antonio hasn’t elected a new mayor since 2017 and whoever replaces term-limited Mayor Ron Nirenberg will immediately inherit a city at a crossroads. They’ll be responsible for the city’s approach to major economic development projects, as well as an increasingly precarious social safety net and fraying relationships with state and federal leaders.

Yet years of well-intentioned policy decisions aimed at making local elections more fair have backfired — creating a confusingly crowded race in which money is more critical than ever to break from the pack.

This year Rolando Pablos, who served as Texas Secretary of State under GOP Gov. Greg Abbott, became the face of the a multi-million dollar effort to build a bench of conservative allies in the state’s historically blue urban centers.

And Gina Ortiz Jones, who was Democrats’ nominee for two high-profile congressional races, has the backing of national Democrats who’ve become desperate to keep Texas from falling further from their party’s reach.

The long list of candidates also includes a number of local elected officials, business leaders and activists with pockets of supporters behind them — meaning it’s unlikely any of the candidates will take the 50% support required to avoid a June 7 runoff.

With few opportunities left to differentiate themselves through message alone, candidates are running out of time to make their cases.

“I think there’s seven candidates that have a shot,” said former mayor and Bexar County Judge Nelson Wolff, one of the few local officials who has offered up an endorsement in the race, in reference to four sitting councilmembers, Pablos and Jones, plus political newcomer Beto Altamirano, his pick.

“But as you come down to the election, it depends on how much money they’ve got at the end.”

The next look at candidates’ campaign finance reports will come Thursday. Yet notably absent from the race right now are any of the local groups that could provide a counterweight to the spending coming from the state and federal level.

The San Antonio Police Officers Association, the San Antonio firefighters’ union, the union representing city employees (AFSCME), the progressive Texas Organizing Project and even Nirenberg have all declined to weigh in until at least the runoff.

The only independent polling on the race, conducted Feb. 17-20 by UTSA, found none of the candidates breaking single-digit support, and roughly 56% of likely voters said they were either unfamiliar with the candidates or undecided.

“I don’t think we’ve ever had this many opponents, and it’s confusing and difficult for the voters,” Wolff said. “Somebody’s going to get in the runoff with probably 20% to 25% of the vote … so who knows how this is going to turn out.”

Anatomy of an unusual race

San Antonio’s public officials have long looked for ways to remove the barriers to run for office in one of the nation’s most impoverished large cities.

A $1,000 individual contribution limit for mayoral hopefuls, instituted during the Julián Castro era, was meant to prevent those with wealthy supporters from buying an election.

Instead, it led to a rise in political action committee activity and self-funders who can put unlimited funds into their own races, while candidates who need to raise the money $1,000 at a time will never reach the roughly $1 million strategists say is needed to fund the modern mayoral race.

Voters line up at Mission Branch Library for the general election in November. Credit: Brenda Bazán / San Antonio Report

At the same time, the city has long rejected raising its $100 filing fee (set in 1974) to ensure candidates from all economic backgrounds can run.

But political strategists say setting such a low bar to make the ballot, compared to other Texas cities with higher fees or petition requirements, actually discourages voter participation.

“[Research indicates that] when you talk to non-voters, the reason they don’t vote or they’re not registered to vote is because they feel like they’re not smart enough or they don’t have the information to make an informed decision,” said longtime San Antonio political strategist Laura Barberena, who is working on Councilman Manny Pelaez‘s (D8) mayoral campaign.

Adding to the distractions, she noted, for the first time in history, this year’s crowded municipal election will overlap with major events in the annual citywide Fiesta celebration, like the King William Fair and the Fiesta Flambeau Parade.

“Now you’ve got 27 people [running], … and it’s really too much,” she said. “People are discouraged from participating.”

A rare chance to move up

Against that backdrop, local political talents that had long prepared to run for higher office have watched candidates from outside City Hall take up much of the political oxygen.

All four current San Antonio City Council members running have relatively liberal social views and a pro-business ideology, and spent the past two years jockeying for advantages like campaign staff and potential endorsements.

Pelaez, a business attorney representing the city’s wealthy Northwest side, sought to carve a lane for himself with promises to crack down on encampments, squatters and panhandling — a bold move in a city with many progressive voters.

He also put his own money into the race to lock down the help of Barberena, who had worked for nearly all of the council’s mayoral hopefuls in the past.

(From left) Beto Altamirano joins city councilmembers Adriana Rocha Garcia, John Courage, Melissa Cabello Havrda and Manny Pelaez at a Jefferson neighborhood association meeting in August. Credit: Miranda Liguez / San Antonio Report

Northside Councilman John Courage (D9), meanwhile, kicked off his campaign some 16 months out from the election — a long enough runway to decide he was too old for the job when the race grew closer. The longtime Democratic activist entered the race with some of the biggest natural advantages, having pulled off many tough victories in some of the city’s reddest territory.

But after voters approved longer terms that would make him 78 by his first reelection, he threw his support behind Southside native Adriana Rocha Garcia (D4), who brought a compelling personal narrative of attending college on a Rey Feo scholarship and completing two advanced degrees as a single mother.

Coming from a district with low voter turnout and few wealthy donors, Rocha Garcia was left to assemble a campaign of primarily volunteers, to which Courage was a welcome help — had he not shocked political watchers by rejoining the race minutes before the deadline in February.

Westside Councilwoman Melissa Cabello Havrda (D6), a disability attorney, underwent a political evolution leading up to the race and spent the past year courting progressives with an effort to fund out-of-state abortion travel through the city budget.

But she would later watch many of those local progressive endorsements instead flood to Jones, who launched her campaign on the same day.

By the January campaign finance deadline, the candidates with partisan supporters were running away with the fundraising.

From the outside lane

Among the first to capitalize on the crowded race of insiders was Altamirano, a 35-year-old tech entrepreneur from the Rio Grande Valley who spent his early career working in Democratic politics.

San Antonio hasn’t elected a mayor from outside the City Council since 2005, when business attorney Phil Hardberger defeated then-Councilman Castro.

But in a city with a business community that’s been at odds with city leaders in recent years, Altamirano, who now owns an artificial intelligence company, charmed even some conservatives by vowing to bring change to City Hall.

Attendees at the Jefferson neighborhood association meeting were handed flyers by Altamirano’s campaign. Credit: Miranda Liguez / San Antonio Report

Over the course of a year-long “listening tour,” Altamirano reeled in influential supporters by seeking help shaping his blank-slate policy agenda, and his self-funded campaign brought on one of the city’s most prominent Republican-leaning consultants, Kelton Morgan, to help introduce those freshly minted ideas to voters.

“He spent a great deal of time on developing the final highlights of what he’s campaigning for,” said Wolff, who became a fan of Altamirano after the latter said he was inspired by Wolff’s book on leadership principles: “Beto is new, a fresh voice, whether people like that or not, we’ll have to wait and see.”

The nonpartisan mirage

In the coming months, however, none of those résumés or records would seem to matter that much in a race where nonpartisan local issues have gone by the wayside.

Nirenberg’s time as mayor turned him from political centrist to partisan warrior over the course of numerous culture war and local control fights with state GOP leaders, and in later years, he allied with a Democratic presidential administration that was eager to invest in historically underserved communities.

Now some of the best-funded candidates to replace him would start the job already in their respective partisan corners.

Pablos is an attorney with a long career in economic development working along state GOP leaders. While he entered the race with little name ID, he spent his early months quietly working on a different approach to fill out his policy agenda: Launching a think tank to advise on local policy, such as San Antonio’s city-owned utilities, SAWS and CPS Energy.

Pablos said last year that he planned to raise money for the think tank, then turn it over to a board of directors if he becomes mayor.

Mayoral candidate Rolando Pablos speaks at a press conference in the Mariachi Bar of Mi Tierra on Thursday. Credit: Brenda Bazán / San Antonio Report

An Abbott-aligned PAC said it intended to raise $2 million to help Pablos, and sent an email to prospective donors earlier this year advertising the group’s ability to “accept unlimited funds from corporations, individuals, and PACs.”

“Local elections are a critical foundation for building future conservative influence,” the group’s political strategist Mitchell Carney said in a Jan. 29 internal donor memo.

Jones is a seasoned campaigner backed by Emily’s List, Vote Vets and a number of sitting U.S. senators and congresswomen, and was supported by many local Democrats in past races.

But she moved back to San Antonio less than two years ago, when she finished her post in the Biden Administration, and her knowledge of city issues will involve some catching up.

Gina Ortiz Jones speaks at a January campaign press conference. Credit: Brenda Bazán / San Antonio Report

Pelaez has shifted his message to match the now-partisan nature of the race, positioning himself as ready to fight GOP leaders at the state and federal level.

“We’ve got a governor and an attorney general who made no secret, right, that their knives are sharpened for what they consider to be cities that betray the worldview held for the governor,” he said in a January interview.

Pablos, meanwhile, has also undergone a messaging reboot.

Though he started the race focused on local issues, he’s started playing up his connections with state leaders in a race where former Northside Councilman Clayton Perry is also angling for the conservative lane.

“Wouldn’t you want someone who actually can have good relationships with our state leadership and not be fighting with them all the time?” Pablos told the San Antonio Report. “These are the people in Austin who control state funding.”

Andrea Drusch writes about local government for the San Antonio Report. She's covered politics in Washington, D.C., and Texas for the Fort Worth Star-Telegram, National Journal and Politico.