If President Barack Obama's goal at the fifth Summit of the Americas in Trinidad and Tobago this weekend was to be better liked by the region's dictators and left-wing populists than his predecessor George W. Bush, the White House can chalk up a win.

AP

Hugo Chavez and Barack Obama.

If, on the other hand, the commander in chief sought to advance American ideals, things didn't go well. As the mainstream press reported, Mr. Obama seemed well received. But the freest country in the region took a beating from Venezuela's Hugo Chávez, Bolivia's Evo Morales, and Nicaragua's Danny Ortega.

Ever since Bill Clinton organized the first Summit of the Americas in 1994 in Miami, this regional gathering has been in decline. It seemed to hit its nadir in 2005 in Mar del Plata, Argentina, when President Nestór Kirchner allowed Mr. Chávez and his revolutionary allies from around the region to hold a massive, American-flag burning hate-fest in a nearby stadium with the goal of humiliating Mr. Bush. This year things got even worse with the region's bullies hogging the limelight and Mr. Obama passing up a priceless opportunity to defend freedom.

Mr. Obama had to know that the meeting is used by the region's politicians to rally the base back home by showing that they can put Uncle Sam in his place. Realizing this, the American president might have arrived at the Port of Spain prepared to return their volley. They have, after all, tolerated and even encouraged for decades one of the most repressive regimes of the 20th century. In recent years, that repression has spread from Cuba to Venezuela, and today millions of Latin Americans live under tyranny. As the leader of the free world, Mr. Obama had the duty to speak out for these voiceless souls. In this he failed.

The subject of Cuba was a softball that the American president could have hit out of the park. He knew well in advance that his counterparts would pressure him to end the U.S. embargo. He even prepared for that fact a few days ahead of the summit by unconditionally lifting U.S. restrictions on travel and remittances to the island, and offering to allow U.S. telecom companies to bring technology to the backward island.

Think that helped cast the U.S. in a better light in the region? Fat chance. Raúl Castro responded on Friday from Venezuela with a long diatribe against the Yankee oppressor and a cool offer to negotiate on "equal" terms. In case you don't speak Cuban, I'll translate: The Castro brothers want credit from U.S. banks because they have defaulted on the rest of the world, and no one will lend to them anymore. They also want foreign aid from the World Bank.

Anyone who thinks that Raúl is ruminating over free elections is dreaming. Nevertheless, the Cuba suggestion to put "everything" on the table became the "news" of the summit. And while it is true that Mr. Obama mentioned political prisoners in his list of items that U.S. wants to negotiate, he could have done much more. Indeed, he could have called Raúl's bluff by putting the spotlight on the prisoners of conscience, by naming names. He could have talked about men like Afro-Cuban pacifist Oscar Elias Biscet, who has written eloquently about his admiration for Martin Luther King Jr., and today sits in jail for the crime of dissent.

The first black U.S. president could have named hundreds of others being held in inhumane conditions by the white dictator. He could have also asked Brazil's President Lula da Silva, Chile's President Michelle Bachelet and Mexico's Felipe Calderón where they stand on human rights for all Cubans. Imagine if Mr. Obama asked for a show of hands to find out who believes Cubans are less deserving of freedom than, say, the black majority in South Africa under apartheid or Chileans during the Pinochet dictatorship. Then again, that would be no way to win a popularity contest or to ingratiate yourself with American supporters who are lining up to do business in Cuba.

Instead the U.S. president simply floated down the summit river passively bouncing off whatever obstacles he encountered. The Chávez "gift" of the 1971 leftist revolutionary handbook "Open Veins of Latin America" followed by a suggestion of renewing ambassadorial relations was an insult to the American people. Granted, giving the Venezuelan attention would have been counterproductive. But Mr. Obama ought to have complained loudly about that country's aggression. It has supported Colombian terrorists, drug trafficking and Iran's nuclear ambitions. As former CIA director Michael Hayden told Fox News Sunday, "the behavior of President Chávez over the past years has been downright horrendous -- both internationally and with regard to what he's done internally inside Venezuela."

Too bad Mr. Obama didn't have a copy of the late 1990s bestseller "The Perfect Latin American Idiot" as a gift for Mr. Chávez. Another way Mr. Obama could have neutralized the left would have been to announce a White House push for ratification of the U.S.-Colombia Free Trade Agreement. That didn't happen either. He only promised to talk some more, a strategy that will offend no one and accomplish nothing. It is a strategy that sums up, to date, Mr. Obama's foreign policy for the region.