Antagonist, cold-war socialism, rogue nations — the prime minister didn't hide his disdain for left-wing leaders like Venezuela's Hugo Chavez. His former spokesman awkwardly referred to Latin America at the time as Canada's "backyard."
Harper arrived in this historic seaside town on Friday for the sixth summit in a political and economic landscape that might require a shift in vocabulary that would resemble the change in his thinking and rhetoric on China.
Brazil, Argentina, Chile and Peru have largely weathered the global economic downturn and some are forecasting impressive growth this year. China has poured billions into projects in the region, becoming Brazil's largest trading partner.
There is also more unity among Latin American countries than ever before — a new organization called the Community of Latin American and Caribbean States (CELAC) was born last December and specifically excludes Canada and the United States.
Hal Weitzman, author of "Latin Lessons: How South America Stopped Listening to the U.S. and Started Prospering," says the region is simply not as desperate anymore for foreign investment.
"It's important for Canada and any large developed country to remember that the dynamic has changed and you're not just competing with the U.S. to show that you're not American, but there are a whole load of other investors who are prepared to come in on very different terms and under very different conditions," said Weitzman.
"It's like a long-term investment to get involved in Latin America now and to treat them as partners and to listen," he adds.
Harper did have some news right off the bat, announcing that Canada has reached a first-time air transport agreement with Colombia, as well as Open Skies-type agreements with Honduras, Nicaragua, Curacao and Saint Maarten.
The agreement with Colombia allows airlines to operate passenger and all-cargo services between the two countries and to combine such air services with select third countries. As well, the deal allows maximum flexibility relating to air services using the flights of other airlines, commonly referred to as code-sharing, which supports efforts by Canadian and Colombian air carriers to expand services.
He also inked a memorandum of understanding with Colombian president Juan Manuel Santos on security, giving the South American country $1 million over two years to in turn help law enforcement agencies in Guatemala and Honduras. Grappling with the drug traffickers is with which Colombia has ample experience.
Harper and U.S. president Barack Obama, however, are already hearing that the rest of the hemisphere acts as a block on certain issues.
All nations, with the exception of Canada and the U.S., are unequivocal in their support of Cuba returning to the Summit. Ecuador's Rafael Correa is boycotting the summit because of Cuba's absence.
"I hope this will be the last summit without Cuba," Santos, the summit host, said this week.
On that front, Harper's language doesn't seem to be softening.
"This is a meeting of democracies and Cuba is the outlier here," Harper's director of communications Andrew MacDougall said Thursday.
There is also a growing consensus among the Latin Americans for a new approach to the war on drugs in the face of catastrophic violence, and on support for Argentina's claim on the Falkland Islands — called the Malvinas by that country.
Canada isn't keen to wade into either of those issues. Harper will not budge on the question of legalizing drugs and thinks the Falklands is a bilateral issue best left to the countries involved.
But where Canada is hoping to find some common ground at the summit is on trade. In 2009, there wasn't much excitement on that front — this year's theme is "Connecting the Americas: Partners for Prosperity."
Harper met with nine Canadian CEOs at a roundtable Friday shortly after arriving in Cartagena. They included Scotiabank president Rick Waugh and former Conservative cabinet minister Jim Prentice, senior executive vice-president of CIBC.
"I'm looking forward to chatting with you all about what Canadian industry is doing here in the Americas," Harper told the group. "This has been an area of tremendous growth in Canadian trade and investment activity since our government has taken office."
Harper has been enthusiastically courting Brazil, now the world's sixth largest economy. And the Conservative government is relying on some of its friends in the region to back its bid to join the Trans-Pacific Partnership (TPP), a proposed tariff-free zone of nine countries.
Weitzman says if Canada and the U.S. want to make some serious headway, they need to abandon their damaging habit of playing ideological favourites in the region — something China and Brazil don't do.
"(Harper) likes Colombians, he doesn't like the Venezuelans, he doesn't like the Ecuadorians. I think this idea of choosing friends in a way that we used to in the Cold War is very old fashioned and we don't have that approach to China or even Saudi Arabia," said Weitzman, a Financial Times correspondent based in Chicago.
The Conservatives are trying to inject some new life into the government's so-called Americas Strategy, a policy of increased engagement in the region centred on three pillars: prosperity, democratic governance and security.
"When you look at South America, there are pretty dynamic economies down there, and these are also economies that are of great interest to Canada because we know by engaging with them on trade and investment we can move people out of poverty into the middle class," Trade Minister Ed Fast said in an interview.
"By doing so you also strengthen democratic governance, you can strengthen environmental rigour, you can strengthen labour laws."
Harper is scheduled to address a CEO Summit of the Americas on Saturday, and will also meet with Canadian businesses in Chile during a bilateral visit on Monday.
By contrast, there is very little involvement by Canadian non-governmental organizations in a series of civil society meetings attached to the summit. Consultations on the revitalized Americas Strategy were heavily weighted to the trade side.
Concerns have been raised about Canadian mining companies in Latin America and their treatment of the environment and indigenous people. There are also worries about continuing violence against labour figures in Colombia, and of journalists across the region.
"Investors rights are totally primary, and labour rights, forget it. I mean, look at what's happening in Canada," said Sheila Katz of the Canadian Labour Congress.
"(Harper's) declared war on Canadian unions, and then he goes and negotiates a free-trade agreement with Colombia which has the absolute worst record of labour violations and highest rate of murders of trade unionists in the world."
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