Posted on Fri, Jun. 29, 2012

When Enrique Santos was attending Jose Marti Middle School in Hialeah, or registering to vote Republican like the rest of his Cuban émigré family, or becoming an exile hero for prank calling Fidel Castro on his hit radio show El Vacilon de la Manana, he never would have imagined he’d end up where he was Tuesday night.

But there he was, onstage at the Fillmore Miami Beach, emceeing a fundraiser for Democratic President Obama, speaking (mostly) seriously about healthcare and immigration policy, and announcing to the world that he was a “proud member of the LGBT community.”

“What happened is I’ve evolved, the same way all of us do,” Santos said Wednesday morning at a Design District café. He was red-eyed after celebrating his debut in the political big-time into the night, then rising to host his 6 a.m. show on Miami station Mix 98.3 FM.

“We live, we learn, we’re not the same person today we were yesterday.”

And how. Whether the evolution of Santos, 37, is an aberration or part of a generational change for the Miami-born children of Cuban exiles is impossible to know. Santos says he just wants to think for himself. But as the host of a popular radio show on a major Miami station owned by powerful Spanish language media company Univision, his thoughts are potentially influential.

And while irreverence and pranks are still part of the mix, he has become more serious about his role. “I realized I can make a difference,” he says. “There’s a time to be funny, and a time to be serious. I can be a voice of reason to the masses.”

Reason was not a word anyone would have applied to Santos during much of the last decade, when he and Vacilon co-host Joe Ferrero specialized in over-the-top satire and outrageous on-air stunts. Their 2003 prank calls to Venezuelan president Hugo Chavez and Cuban leader Fidel Castro made them heroes in the exile community.

Santos was the wilder of the duo – he even faked his own death one April Fool’s Day. But a series of events prompted some soul-searching.

In 2005 Santos ran for mayor of Miami, entering the race at the last minute in what was meant to be another stunt. But the experience of campaigning (on hiatus from his show) and hearing firsthand about the city’s problems made a strong impression. To the astonishment of observers and Santos himself, he came in second to Manny Diaz with 26 percent of the vote.

During the 2008 presidential campaign, he had Joe Biden (by phone) and John McCain (in person) as guests on his then-solo show. He and the Republican candidate played Hungry Hippo, a board game that was a childhood favorite of Santos’ – not exactly Nightline material. He voted for McCain, although he says he “wasn’t upset” that Obama won.

Then things began to change. His support for rock star Juanes’ 2009 Havana concert —Santos called for “freedom for Cuba, respect for Juanes” — prompted some in the exile community to turn on him.

“I thought, ‘Why am I a bad Cuban? Am I a better Cuban by breaking [Juanes’] CDs? I’m not doing him, or the community, or Cuba, or myself any good.’”

And while he is still a strong opponent of Castro’s government and a defender of the passion, pain and history of exile Miami, Santos began changing his mind about what those ideas meant to him.

“I came from the traditional Miami thinking, that tradition of standing at Versailles drinking a cafecito with a big sign saying Abajo Fidel. I began re-programming my thinking.”

Later that year, to his surprise, Santos was invited to the Obama White House for a Hispanic Heritage celebration, with Gloria Estefan and Marc Anthony performing. At the time, his younger brother was serving in Iraq. He felt a heady mix of pride, confusion and worry for his brother.

“It was very emotional,” he says. “I realized this is democracy at its best. I didn’t vote for [Obama] and his administration invited me. How many people in Latin countries say one word against the government, and they’re X’d out?”

The sense of momentous occasion didn’t keep him from asking just-appointed Supreme Court Justice Sonia Sotomayor to dance a little salsa. “Then it was time to have fun,” he says.

Joe Garcia, the former executive director of the Cuban American National Foundation, who has known Santos since his Vacilon days, says he is maturing.

“He’s having a personal journey, getting out of the same back and forth, thinking instead of being a shock jock,” says Garcia, who had a similar odyssey, from conservative exile leader to liberal Democrat. (He’s running for Congress against Republican U.S. Rep. David Rivera.)

“He’s a man at peace with himself. He has the ability not to be afraid. It’s not about arguing with someone else anymore, it’s about ‘Here’s where I am,’ ” Garcia says.

For Santos, the final push came when the president repealed Don’t Ask, Don’t Tell. Although he came out to his parents over a decade ago, there was plenty of homophobic and macho sexual humor on the Vacilon show, and while Santos says he hasn’t hidden his orientation, he has not been public about it, either.

He made a connection between the repeal of a law he felt was deeply wrong and the way he felt as a teenager “with no one talk to about how I felt, and all the guys talking about girls, and thinking, ‘Am I the only one who feels this way?’”

“You’re asking somebody to put on a uniform and risk their life, which is this country’s greatest honor, and yet you’re telling that person to lie?” Santos asks. “C’mon.”

From the stage at the Fillmore Tuesday night, Santos saluted his guest, Walter Burttschell, a former Marine discharged because of Don’t Ask, Don’t Tell. He praised the president for his stance on gay marriage and the Dream Act, “as a proud member of the LGBT community and a Latino.”

Backstage, startled campaign workers asked, “Did you just come out onstage?”

His remarks had their lighter moments, too. He joked that “this is the coolest president I’ve ever met, and the only president I’ve ever met,” and that healthcare reform meant “our abuelos and abuelas won’t have to visit a santero or a botanica anymore when they’re sick.”

But he saw a larger purpose to his banter.

“Being in tune with my audience is very important to me,” Santos says. “We can still have fun. But times are different now. I’ve noticed I have an ability to do something positive, to strike a chord with people. I’m not telling people what to do. I’m just telling them my reasons for what I’m doing.”