“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For Santos, the final push came when the president repealed Don’t Ask, Don’t Tell.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.”