SAN ANTONIO’S mayoral races tend to be long-running telenovelas—pitched battles with stark choices, high stakes, roiling emotion, and plenty of drama. Past elections have pitted Anglos against Hispanics, Republicans against Democrats, and environmentalists against business boosters. The May 7 election is still months away, but already two new twists have been added to the plot: insiders against outsiders and youth against age. The leading candidates are Julián Castro, a thirty-year-old city councilman who is one of the state’s rising Hispanic political stars; Carroll Schubert, a pro-business councilman who is a former Republican precinct chairman; and Phil Hardberger, a seventy-year-old retired appellate judge who has long been active in Democratic politics.

It is the presence of Hardberger, a newcomer to the nonpartisan politics of city hall, that makes this race different from all that have gone before. It’s an unwritten rule here that outsiders don’t run for mayor; for more than half a century, the position has been reserved for insiders who have served on the city council. The rule held true in the sixties, when San Antonio was run by Mayor Walter McAllister and a small group of Anglo businessmen known as the Good Government League. It was true when the GGL unraveled in the seventies and San Antonians decided they needed a bridge-building Hispanic as mayor. That led to the election of Henry Cisneros, in 1981, after he had served on the council for six years. He went on to serve eight intense years that were filled with emotional highs and lows and constant exhortations to greatness. It was true of all the mayors who came after Cisneros, most notably Lila Cockrell, who depressurized the city after the frenzied Cisneros years; Nelson Wolff, who sped up the pace again; and currently, Ed Garza, whose three-plus years in office have seen major scandals and minor accomplishments. Most of these mayors had long enough histories at city hall that they were referred to by their first names: Mayor Mac, Henry, Lila, Nelson. In San Antonio, politics is intimate and personal and tends to reflect not only the will of the voters but also the psyche of the city. And right now the psyche of the city senses that things are on the wrong track at city hall, so much so that the time may have come to consider an outsider.

The Garza years have given youth a bad name. He was only 32 years old when he took office, in 2001, a year younger than Cisneros had been twenty years earlier. But Cisneros’s political skills were instinctive and seasoned, while Garza’s are neither. A landscape architect by training, with a mild, sometimes plodding personality, Garza has focused on the process of local government rather than on big projects. (In eight years Cisneros passed six bond issues totaling $526.8 million for streets, drainage, and public buildings; so far Garza has passed one, worth $115 million.) Early in his term, the council became ensnared in a bribery scandal. One current and two former council members were caught on tape demanding payoffs in exchange for votes. All three were convicted.

When Garza did take on a political challenge—reforming the city charter—it soon became clear that he did not know how to build coalitions and that his powers of persuasion were limited. He inflamed the business community with his on-again, off-again support for PGA Village, the Professional Golfers’ Association’s planned golf course, resort, and residential and commercial development on a 2,600-acre site on the North Side. After a three-year fight with environmentalists, who opposed the development because it was to be located over the Edwards Aquifer recharge zone and might have adversely affected the city’s drinking water supply, the PGA pulled out of the deal in May. Garza got the blame. Last spring Garza led an effort to pay the mayor and the city council ($41,000 for the mayor and $31,000 for each council member) and lengthen San Antonio’s strict term limits (two 2-year terms) for city offices. The proposal failed in every council district. In August he lost more support when he botched the firing of beleaguered city manager Terry Brechtel by calling her at home at ten-thirty at night, summoning her to city hall, and demanding her resignation on the spot. (She refused, then resigned several days later.)

But Garza is not the only problem. There is a growing recognition among San Antonio politicians and business leaders that another culprit at city hall is term limits. San Antonio has the shortest term limits of any large city in Texas and the most inept local government because of it. In Houston the mayor and council members can serve a maximum of six years; in Dallas the limit is eight years, twice as long as San Antonio’s four years. Garza’s experience illustrates the two major problems of the system. First, severe term limits do not give council members enough time to learn the ropes or the issues or to build citywide constituencies. It takes time to master coalition politics—to reward team play and punish divisive behavior. Garza didn’t have the skills, nor did he have the time. He served the maximum four years on the council, keeping close ties to his central city district. If he could have run for a third term, he would have done so. Instead, he was forced to either leave city hall or run for mayor before he was ready. Now he has to leave the job before he has learned it. The second problem is that term limits can provide an incentive for corruption. With such a short time in office, politicians who see the end of their careers approaching are susceptible to the temptation to get as much out of the office as they can before being forced to move on. Since term limits were put in place in San Antonio, in 1991, city government at times has resembled that of a banana republic: a toxic mix of corruption and ineptitude that makes good government difficult, if not impossible.

With Julián Castro waiting in the wings to succeed Garza, a phrase began to circulate around town about a year ago: “San Antonio needs a grown-up for mayor.” That’s when business leaders, community groups, prominent Hispanics, and old friends in the Democratic party began talking to Phil Hardberger about running for mayor. “Everywhere I went, I kept hearing the same line [about a grown-up],” Hardberger recalls. Hardberger was not only a grown-up in age but also in political experience. A native of Morton, in West Texas, Hardberger moved to San Antonio in January 1970 with his wife, Linda, and became a well-known plaintiff’s lawyer. He was elected to the Fourth District Court of Appeals in 1994 as a Democrat and retired as chief justice in 2003. He has profited from a lifetime of building relationships across partisan and ethnic lines, getting encouragement to run from high-profile Republicans such as developer Cliff Morton, car magnate Red McCombs, businessman Mike Beldon, and party activist Janelle McArthur. His Democratic credentials earned him the backing of Hispanic politicians like congressmen Charles Gonzalez and Ciro Rodriguez and Sheriff Ralph Lopez. Still, Hardberger at first decided against making the race. He and Linda went ahead with plans to take an extended sailing trip up the East Coast on his 42-foot cruiser. While they were under way, the “draft Hardberger” campaign continued by e-mail. Finally, when he came back to San Antonio for Fiesta,  in April, Hardberger changed his mind. “The city’s broken,” he told me recently. “But I think I can fix it.”

Hardberger’s two opponents, Castro and Carroll Schubert, both have served the maximum four-year terms on the council. Like Garza four years ago, Castro would not be running for mayor if term limits had not forced his hand. His two biggest problems are his age (he not only is young, he also looks so darn young) and his close association with Garza. The two are from the same city council district. They both had reservations about the PGA Village project and both wanted to fire the city manager. But he is much more polished than the mayor and possesses superior political skills. His demeanor reminds you of the smartest, best-prepared kid in class, the one who doesn’t have to blurt out the right answers because everyone knows he’s got them down cold. In Cisneros-like style, he has a clear vision for San Antonio—“a world-class city with a small-town quality of life”—and knows how to articulate it. He has a strong grassroots organization that is headed by his mother, Rosie, an early member of the Raza Unida movement and a longtime political activist who ran unsuccessfully for city council in 1971. He also has the support of Cisneros, who went to kindergarten with Rosie and whose daughter, Mercedes, attended Stanford University with Julián and his twin brother, Joaquin, a member of the Texas House of Representatives. But he’ll be outspent by Hardberger and Schubert, and Hardberger will make inroads into his Hispanic base.

Schubert has strong support in his North Side district and has solidified his standing among the many women’s groups within the Republican party. He was an early supporter of PGA Village and opposed firing the city manager, so he does not carry Garza’s baggage, as Castro does. But he is part of the culture at city hall, and that won’t help him. His affiliation as a Republican probably won’t help much either; it’s been more than three decades since San Antonio had a mayor who identified himself as a Republican.

The demographics of San Antonio mean that Anglo and Hispanic candidates are frequently pitted against each other. When Cisneros was elected mayor, he won by piling up huge margins in largely Hispanic precincts and as much as 45 percent of the vote in Anglo areas. Ten years later, when Nelson Wolff won in a runoff against Maria Berriozabal, he did it by carrying two inner-city council districts, one largely Hispanic and one black, as well as a majority of Anglo voters. Hardberger should be able to duplicate Wolff’s winning strategy. Castro faces a more difficult task. In order to win, Castro would have to persuade at least 30 percent of Anglo voters to vote for him. Given his association with Garza and his lack of experience, that doesn’t seem likely.

In a town weary of insider politics and a city hall stifled by term limits, Hardberger may be the right man for the times—an outsider with no ambition other than to be mayor for four years. But not all San Antonians agree with the premise that the city needs a grown-up for mayor. For instance, state representative Mike Villareal, who supports Castro, says he doesn’t think the question is whether Castro is too young to be mayor but whether Hardberger is too old. “Seventy!” says Villareal, who himself is 33. “That’s pretty old to start a career at city hall.” But that’s just the point. Hardberger won’t be starting a career. He’ll be finishing one.