JOHN WATSON-RILEY/AP

It is half past midnight on a summer Friday, and Joe Garcia, the Democratic candidate for Florida’s 25th Congressional District, is holding court outside a South Beach bar. With his mass of dark curls (friends call it the “Joe-fro”) plopped atop a tall but none-too-slender frame, he has to do very little to attract attention. Compound his physical heft with his prominence in the local community, and it’s obvious why every few minutes another twentysomething spots him and says hello. “We have no idea who that girl is,” Garcia whispers sheepishly after one enthusiastic young woman greets him with an air of familiarity.

In the eyes of many young Cuban-Americans, Garcia, 44, is the next political rock star. In the eyes of the Democratic Party, he may be just the right candidate to break the Republicans’ longtime stranglehold on the region. But to older Cuban-Americans, especially those who are part of the historic “exile community,” Garcia is an ungrateful former favorite son who represents all that is wrong with the younger set, particularly in his skepticism toward the Cuban embargo and the old-line, hardline mentality that gave birth to it.

The exile old guard has triumphed in South Florida since almost immediately after the Castro revolution. And since Ronald Reagan’s 1980 presidential campaign, the Republican Party has reaped the benefits. The most popular strategy for Republicans running statewide is to jack up the score among Cuban-American voters, who are numerous enough to offset losses among Jews, African-Americans and union members. It was the basis for Republican Charlie Crist’s gubernatorial victory in 2006, as well as that of his predecessor, Jeb Bush. In 2006 more than 72 percent of all Cuban-Americans in Miami-Dade and Broward counties identified as Republicans.

Garcia’s candidacy is part of what might be called the Democrats’ triangle offense in the region. Frustrated with targeting specific districts and losing, the party has attempted to harness the political wind at its back and put forth three strong candidates to challenge three Republican incumbents simultaneously. In the district next to the 25th, Raul Martinez, a Cuban-American dead ringer for Boris Yeltsin who served for more than twenty years as the mayor of Hialeah, is taking on Lincoln Diaz-Balart. In the 18th, there’s Annette Taddeo, a businesswoman running a bit of a long-shot campaign against the relatively moderate Ileana Ros-Lehtinen.

But it is the candidacy of Joe Garcia, a longtime community and party activist, that poses the largest threat to the virulently anti-Castro, pro-embargo status quo. Garcia is running against Mario Diaz-Balart, younger brother of Lincoln, who entered Congress in 2002 and whose district encompasses Miami-Dade and most of the state’s southern tip. An early October Telemundo poll showed Garcia trailing by two points, 41-43 percent, within the margin of error, the best of the three challengers. Diaz-Balart recently agreed to a last-minute debate, to be held October 10, a sure sign of trouble for any incumbent.

While Garcia is only a little younger than Diaz-Balart, he’s the leading member of a generational wave that some think is due to break and, in the process, usher out the way politics has worked here for decades. “They’re not just running against me,” Garcia says of his opponents. “They’re running against history.” But to make history, Garcia will have to defeat it first; as his opponents know well, history–long bloodlines and memories–is pervasive here, as inescapable as the sweltering sun.

Cuba policy was once all that South Florida politics orbited around; Garcia intends to reform the embargo and make US-Cuba relations only a part of the political constellation alongside more routine kitchen-table issues. Garcia’s professional life began in 1988, when Jorge Mas Canosa–widely credited with creating Cuban-American power by founding the Cuban American National Foundation–tapped him, while still in law school, to lead something called the Exodus Relief Fund. The fund, which operated under CANF, was set up to reunite family members who had fled to America from Castro’s Cuba with those who had fled to other countries, like Spain and Venezuela. Footage from family reunions that the project put together is now on YouTube, most of it featuring weeping family members embracing after a long time apart.

At the beginning of his career, working with an organization as closely associated with Reagan Republicanism as CANF, Garcia was as much in favor of the embargo as any hardliner. But now he’s the local torchbearer for the opposition, which argues that the embargo hurts the Cuban people, particularly dissidents. Garcia favors allowing more family visits and increasing the amount of money Cuban-Americans are allowed to send back to their relatives still living under Castro. Garcia is not advocating that the embargo end entirely, at least not yet. He’s interested in relaxing its restrictions, especially those it places on ordinary citizens in the United States and Cuba. “People in Cuba are victims. Why the fuck are we squeezing them?” he asks.

This proposed policy change may seem modest, but in South Florida, it’s nearly heretical. The fact that it’s Garcia making the skeptical argument appears to have struck a nerve. After his stint with Exodus, Garcia went on to lead the usually hawkish CANF, which is widely credited as the institutional power most responsible for forging the anti-Castro, pro-embargo, bipartisan coalition in the early 1980s that has dominated the region, as well as the halls of Congress, ever since. That a former leader of CANF would oppose the embargo is greeted with bafflement by such people, who see it as a slap in the face of tradition. “Garcia,” I am told by one long-term Democrat in his 60s who is remaining neutral in this race, “is an opportunist.”

Garcia’s opportunity, as it were, depends on his ability to forge a coalition of multiethnic union members, businessmen and an emerging cohort of young Cuban-Americans intent on breaking from the path followed by their parents. Felice Gorordo and Tony Jimenez, two men at the bar with Garcia, are emblematic of this new generation. They spent their early 20s working at the lower levels of the current Bush White House and were strong believers in the embargo. But they left after Bush’s re-election, disgruntled and disillusioned, convinced that the administration’s harsh rhetoric on Castro was illusory and unlikely to bear results. To them, even the embargo is an illusion. “What embargo?” Gorordo asks, pointing to the hundreds of millions of dollars that have seeped into the island over the past few years. “Cuba policy has reached the point of absurdity,” Jimenez tells me later. Gorordo and Jimenez are now Garcia supporters.

At a mid-June AFL-CIO labor rally on the streets of Miami, Garcia is showered with adoration from the picketers and local leaders the moment he steps out of his car. He rushes to the median, holding up a prolabor sign, and car honk after car honk creates a cacophony of support. The union members are of all ethnic backgrounds; they care about the economic crisis and achieving universal healthcare, both of which Garcia has prioritized. Perhaps not surprisingly, no one can recall Diaz-Balart ever attending a similar rally.

Later that night, Garcia is scheduled to speak at a tony meeting of the United States Hispanic Chamber of Commerce’s national board. While most of the attendees are Republicans, their soft spot for Garcia is obvious. Neither of the Diaz-Balart brothers is in attendance. Several self-identified Republicans–including a man introduced to me as “the father of outsourcing”–say they will break ranks to support Garcia. “Joe is very pragmatic,” one conservative supporter explains. It’s no wonder that Garcia has raised almost $1.3 million, an astonishingly large sum that has caused Realclearpolitics.com to rate the race as one of the most competitive in the country. (Diaz-Balart’s previous challenger never crossed the six-figure threshold.)

But Garcia’s emerging coalition might not be enough to overcome the deep-seated pro-embargo mind-set of the older generation. A poll taken over the summer showed Garcia trailing Diaz-Balart badly among all Cuban-Americans, 65 percent to 26 percent. At the Versailles restaurant–a temple for the old guard, where in the front vestibule a local newspaper’s headline touts John McCain’s Experiencia y Patriotismo!–I have lunch with Nelis Rojas de Morales, secretary general of the Coordinadora Internacional de Ex-Prisioneros Politicos Cubanos (the International Coordinator of Cuban Ex-Political Prisoners). She was born in Cuba, imprisoned for opposing the Castro regime, then imprisoned again in Venezuela. To her, the question of whether to support Joe Garcia is secondary to the larger question: how, and when, can Fidel Castro be overthrown? I ask her if she thinks it ought to be violent. “If necessary,” she replies. “To change the system little by little is to lack knowledge of that system. The Communist system does not change.”

Down the street from the Versailles sits Sentir Cubano, a store that specializes in Cuban tchotchkes. Everything in the store–pictures of elegant night life, posters of old movie stars–depicts a Cuba before Castro. One of the bestselling items is a full-size replica of the Havana phone book from 1958, the moment before the revolution. The store’s manager, Maria Vasquez, is friendly with Garcia but does not support him.

Garcia wants to end all this–the bellicosity of de Morales, the obsessive nostalgia of Sentir Cubano. Yet rumors of the old guard’s demise have been exaggerated before. “Twenty years ago, back then I thought the change was going to be more rapid,” says Lisandro Pérez, a sociology professor at Florida International University. “The fact that here we are in 2008, saying, ‘Gee, we are going to see change,’ when we should have seen it a little while ago. The older generation has died off. What’s interesting is the ability of that historic exile community to reproduce [its] message into the culture.” Garcia comes out of that community but has since diverged onto a broader path. Whether the community is ready to follow him, however, is an open question.