Vicky Huddleston loves to tell the story about the young Cuban hitchhikers in Havana.
As she loaded them in her car, the group was chatty, open and warm – nothing like the strained, often bombastic, U.S.-Cuba relations of the past half century.
"What do you do?" a young Cuban woman in the hitchhiking group asked.
Diplomat Huddleston explained she ran the U.S. Interests Section in Havana.
"Oh, be our mother and take us to Miami!" the cubanita told her, only half-jokingly.
James Cason, who followed Huddleston into the post during President George W. Bush's first term, differs dramatically from Huddleston on what U.S.-Cuba policy should be under the Obama administration.
But they both agree that young people and Afro-Cubans yearn for better than the failed Fidelista police state of the past 50 years.
"They don't need to be convinced to love or understand democracy," Cason told a packed crowd at the University of Miami's Institute for Cuban and Cuban-American Studies Friday night.
"What they lack is a way to influence regime behavior . . .
"The vast majority, especially the youth, no longer trust the so-called revolution to improve their lives."
Cason also points to Cuba's Achilles heel: race.
The Castro brothers have had 50 years to shape their color-blind society, and still, only a handful of Cubans of color are at the highest echelons of power.
Most blacks remain in the worst of the already decrepit and cramped housing stock.
They disproportionately pack Cuba's prisons, many for "crimes" that most everywhere else would carry a fine or be no crime at all.
The elite – the generals that Raul Castro put in charge of Cuba's economy – are white.
So are the vast majority of hotel workers.
Young Afro-Cubans don't see the revolution delivering their due.
"They're afraid of blacks," Cason said of the regime's leaders.
"That's why they don't want them to move from the east" of the island.
That's a crime, too.
Will an Obama administration blow up Cuba policy and push for open trade, and allow American tourists to travel there like they can in China and Vietnam, both human rights abusers?
Or will President Barack Obama only tinker around the edges, keeping the embargo but restoring family-friendly travel policies for Cuban Americans?
(For all the chest-pounding in Havana about the "evil blockade," the current "cash-and-carry" U.S. humanitarian food sales policies makes this country the island's largest supplier.)
Obama likely will take it slowly, use the "critical and constructive engagement" that Huddleston and other diplomats view as the most pragmatic after 50 years of Cuban dictatorship.
The most important factor in any policy change isn't the Cuban exile vote, which Obama didn't need to win in Florida.
What Washington worries about most – whether there's a Democrat or a Republican in the White House – is another rafter crisis.
Anytime a new U.S. president has tried to be bold, the Castro regime has done something to further strain relations.
For now, just having Obama as president sends the strongest signal ever to ordinary Cubans about democracy's promise.