He was a singular sensation even before he stepped onto the tarmac. A "national holiday" was declared to honor the occasion. A two-week spruce up-repave-repaint campaign was undertaken and completed with military zeal. Government employees were paid to line up and wave small Puerto Rican flags on the three possible routes the Secret Service had mapped out for the presidential limousine. But in the midst of this unusual celebration, not everyone in that chorus line was singing. "We cannot greet the colonizer with coffee and cookies," offered Juan Dalmau, gubernatorial candidate of the Puerto Rico Independence Party.
It was not exactly cookies that President Obama's five-hour stopover in San Juan would net, but $1 million in campaign contributions (tickets ranged from $10,000 to $38,000 for a brief encounter at the Caribe Hilton). And so the wheels of American party politics revved up for yet another lap in the "Raise money here, gather votes there" mode that politicians ride when visiting the United States’ most populous territory. The 3.8 million residents of Puerto Rico cannot vote in presidential elections, but the first official visit by a sitting president in fifty years was enough to open pockets and splurge in a presidential campaign of which they will play no part.
"We are grateful people," says Secretary of State Kenneth McClintock. But Dalmau has quite a different take on Obama’s visit: “[It’s] a rehearsal for the next political campaign in which Puerto Ricans are mere extras to court the Hispanic vote in the United States."
Still, the banners that lined the streets marked with pride what was termed a “historic event”: “We are proud to be part of history: Kennedy 1961—Obama 2011.” But beneath the facile historical comparison lies a world and a generation of change. The December 1961 visit by President Kennedy was a leisurely Christmas rest, highlighted by a ticker tape parade through Old San Juan, dinners, concerts by Pablo Casals and a now-famous sleepover (the bed Kennedy used has been given the “President-slept-here” treatment in the official tour of La Fortaleza, the governor's mansion). By contrast, Obama's rush-and-hush trip—a logistical nightmare for local politicians—has proven to be an issue hotter than the sweltering 90 degree temperatures. With Puerto Rico’s 21 percent unemployment rate, 100,000 lost jobs and 500-plus murders in the last five months, the visit seemed a PR mistake. Then there is the issue of Governor Luis Fortuño, a member of the pro-statehood New Progressive Party—who has been a poster boy for the Republican Party and has been mentioned as a candidate for the vice presidency. The rarefied ambience of the oldest colony in the world has not even yielded a reggaeton tune in Obama's honor.
It's been a rude awakening even for Obama supporters here, who have strived to find eloquence in the face of unkept promises, including the perennially unsolved issue of Puerto Rico’s status. Candidate Obama vowed to resolve the status of the island in 2008 and promised to push for status definition upon arrival in the White House. "The White House Task Force Report on the Status of Puerto Rico" was presented to the president and Congress in March. The report’s conclusion leaves the issue of status squarely in the hands of Puerto Ricans, suggesting a referendum. Upon arriving, Obama delivered his status message with half-hearted zest: “When the people of Puerto Rico make a clear decision, my administration will stand by you…. We want Puerto Rico to have a shot at the dream that we all have.”
The status issue in Puerto Rico drives and sustains the whole political and financial scaffolding of the three main parties. The categories of liberal and conservative do not apply here as a natural divide; instead the three camps are drawn along strict ideological lines—Independence, Statehood or Commonwealth for Puerto Rico.
After 113 years under US rule, Puerto Rico is still a complex exercise in contextualization. The island is not prey to generic "Hispanic" politics as they play out on the mainland. Immigration, deportation and raids are not hot-button issues here, as Puerto Ricans have been US citizens by birth since 1917. The most pressing issue—aside from the economy and the wars in Iraq and Afghanistan, in which 111 Puerto Ricans have died so far—is the perception of constant "federal intervention" in local affairs, of which examples abound in the last decade, including the battle to regain control of Vieques from the Navy; the killing of Machetero leader Filiberto Ojeda Ríos  by FBI agents in 2005; and former Governor Aníbal Acevedo Vilá's indictment and subsequent trial for a pay-to-play scheme. Island residents resent the frequency of these interventions, as well as the lack of communication. The perception is that Puerto Rico is not a part of the "national conversation," but rather a colonial outpost in which identity politics, language and nationalism have residents mired in a perennial identity crisis.
Money is, of course, an issue. Obama had a three-hour stopover in November 2007 for fund-raising purposes, but he was accused of using the island as "a giant ATM machine" and of snubbing the press. "It is a pricey carnival of colonial assimilation," says Dalmau. In an island beset this year with a 20 percent increase in its crime rate, the fallout of a new 7 percent sales tax, a declining economy and dissatisfaction with political leaders, embracing hope and holding on to promises seem more pricey than ever. Pocketbooks may open, but it will take more than the obligatory Spanish sentence or two (“Si, se puede") for a politician to connect with Puerto Rico.