So far this cycle, Barack Obama’s political opponents have called him a lot of things: Muslim, elitist, unpatriotic and–least flattering of all–“Barry.” But during today’s John McCain townhall in the Sheraton’s Royal Poinciana Ballroom here in sunny Miami, a middle-aged Cuban-American woman–“trained,” she said, “as a psychologist”–stood up and compared Obama to (ahem) Cuba’s retired Communist dictator Fidel Castro. “I’m seeing the same dreamy-eyed look as I saw among the Cuban youth 50 years ago, unquestioning all of the things that Senator Obama is saying and isn’t saying,” she said. “Can you somehow send a message… that the youth have been targeted with young music, nice words and empty promises while the core of the nation is at stake? Cubans are here 50 years later because we did not question a leader who was nothing but empty promises.” Judging by the thunderous applause, most of the 750 Miamians in attendance didn’t exactly disagree.

Of course, not every Cuban-American in South Florida sees Obama as the second coming of Castro. But the psychologist’s remarks neatly preview one of the major battles awaiting Obama this fall. It’s no mystery why McCain chose to spend his first general-election jaunt through the do-or-die Sunshine State–which just so happened to coincide with Cuban Independence Day–delivering a sweeping speech on Cuban-American relations. Notoriously shaky with the broader Latino electorate, Obama faces a special challenge with the older, hard-line Cuban exiles of Miami-Dade County who oppose any engagement with Castro–and who essentially boosted George W. Bush to victory in this crucial swing state in 2000 and 2004, choosing him over his Democratic rivals by three-to-one margins. When asked during the Feb. 21 Democratic debate whether he would be willing to meet with Raul Castro, Fidel’s brother and successor, Obama said, “That’s correct.” “I would meet without preconditions,” he added. What’s more, while running for the Senate from Illinois in 2003, Obama, who now says he supports taking steps to normalize relations only if the Cuban government moves toward democracy, wrote on a questionnaire that he favored normalizing relations with Cuba–without offering any qualifiers at all.

McCain seized on both statements in today’s tough-talking speech, putting a local twist on his continuing effort to paint Obama as a “naive,” “inexperienced” flip-flopping foreign-policy lightweight (see: Iran). “Just a few years ago, Senator Obama had a very clear view on Cuba,” he said, sarcastically quoting the questionnaire. “Now Senator Obama has shifted positions and says he only favors easing the embargo, not lifting it. He also wants to sit down unconditionally for a presidential meeting with Raul Castro. These steps would send the worst possible signal to Cuba’s dictators – there is no need to undertake fundamental reforms, they can simply wait for a unilateral change in US policy. I believe we should give hope to the Cuban people, not to the Castro regime.” And in response to the Obama-Castro comparison, McCain simply repeated these talking points and quickly pivoted to an attack on Obama’s willingness to meet with hostile heads of state. “Roosevelt didn’t talk with Hitler,” he said. “Reagan didn’t talk with Breznev or his successors.”

After the speech, another Cuban-American woman stood up to praise McCain’s “heroism.” “Thanks for making it very clear in this community that you will have nothing to do with Castro,” she said. “And believe me, for that Florida will be yours.” Just in case you’re wondering how the remarks played with this particular crowd.

That said, Obama’s stance on Cuba isn’t a clear-cut as the Arizona led his audience to believe today–nor is McCain’s itself. During his 2000 presidential campaign, in fact, McCain “stood out for supporting normalizing relations with Cuba, even if Fidel Castro remained in power, provided the government went through certain steps to democratize the country,” as the New York Times put it today. During a 2000 CNN interview, McCain said, “I’m not in favor of sticking my finger in the eye of Fidel Castro,” and reiterated his support for a “road map to normalization” similar to Vietnam’s. And despite saying this afternoon that “the embargo must stay in place” until the Cuban regime “schedule[s] internationally monitored elections,” McCain told the Miami Herald in 1999 that he would be willing to wait on that goal before beginning steps toward normalization. And so on. For McCain, the shift is a matter of tone–from moderation to politically-expedient hawkishness–rather than policy. Still, they make his attacks on Obama’s own moderation–the Illinois senator may not favor “preconditions,” but he’s always advocated for “preparations” that involve “human rights, releasing of political prisoners, opening up the press”–somewhat harder to swallow. In the end, Obama and McCain’s policies towards Cuba don’t differ all that much (even if their approaches to its leader do)–after all, neither would remove the embargo without significant political concessions. But their attitudes–and rhetoric–are miles apart, as McCain homes in on traditional hard-liners and Obama targets a younger generation that favors engagement (and his plan to allow for unlimited family visitation and remittances to the island). We’ll see in November who’s the craftier pol.

For now, McCain has the upper hand. During today’s question and answer session, at least three supporters petitioned the candidate, in heavily-accented English, to help with the release of Cuban political prisoners, noting McCain’s own harrowing five year stay as a POW at the Hanoi Hilton; others, from Venezuela, Haiti, Nicaragua and Colombia, also lauded him for surviving the ordeal. It was clear from these exchanges that McCain’s connection to the Latino voters of Florida–many of whom once suffered under the brutal regimes of Central and South America, and have family or friends who suffer still–is as much about personal experience as policy prescriptions. That’s why McCain headed straight from the Sheraton to “La Casa del Preso,” a boarding house and museum in Miami’s Little Havana dedicated to honoring Cuban political prisoners–and why Obama faces such a steep uphill battle in Florida this fall.

UPDATE, 3:30 p.m.: Team Obama responds by–predictably–linking McCain to President Bush. “John McCain needs to explain why continuing to do exactly what George Bush has done will somehow produce a different result,” says Connecticut Sen. Chris Dodd. “The Senator McCain I used to know was open to negotiations with Cuba to lift the embargo, but now he’s taking a hard line position, embracing a policy that has failed the Cuban people and the American people alike for fifty years. Instead of four more years of George Bush’s policy, Barack Obama will help bring liberty to Cuba through direct diplomacy and change that allows for unlimited family visitation and remittances to the island. It’s time to reject a Bush-McCain approach that has isolated us in our own hemisphere, so that we can have renewed American leadership under Barack Obama.”