Photo credit: Darkwind

They say timing is everything. But in U.S.-Cuban relations, timing is often nothing more than a missed opportunity. Everyone has their own theory about these things. Back in 1996, analysts thought it was a most opportune moment for improved relations. The Helms-Burton Act was stalled and President Clinton appeared to have no intention of signing it. And then Cuban migs shot down two civilian aircraft that Cuba claimed had violated its airspace. (The group that sent the planes on their mission that day, Brothers to the Rescue, claim they did not violate Cuban airspace that day -- though indeed they had previously, even overflying and leafletting Havana.) It might have been an opportune moment, but it turned out not to be.

And then there were the early 2000's, when a Republican-controlled Congress repeatedly bucked its President, voting to end enforcement of the decades old travel ban on Cuba. The Senate Foreign Relations Committee even voted out a bill to lift the ban outright. U.S.-Cuban agriculture ties were at their tightest, and U.S. Cuba food export fever was at its highest. But President Bush had committed to embargo supporters, and his veto threats ensured that House and Senate leaders yanked Cuba reforms out of every bill they rode along. And then in 2003, with Congress leading the charge for U.S. policy reform, Cuban authorities rounded up 75 dissident activists and sending them to jail for collaborating with the U.S. enemy. It could have been a transformational moment, but it turned out not to be.

And then of course, in 2006 and 2008, Democrats swept through Congress, and won the presidency. The new president was even on record as opposed to the U.S. embargo of Cuba, and campaigned on a foreign policy that would win back the respect of the world. Though Cuba policy seemed such obvious low-hanging fruit, the new administration and Congress failed to grasp the opportunity, particularly in the midst of crushing domestic and international crises and larger priorities like healthcare legislation. Meanwhile, Fidel Castro fell gravely ill in 2006, retired from sight and from the presidency in Cuba, and his more pragmatic brother officially took the reins in 2008, broaching topics and raising criticisms of the Cuban system never discussed under the elder Castro's watch. It should have been the long awaited breakthrough moment, but it turned out not to be.

And here we are in 2010.

Last year, the Obama administration broadly authorized family visits and remittances to Cuba (to its credit) but otherwise just tinkered timidly around the edges, despite broad authority to do much, much more. Raul Castro has spotlighted a heap of problems in Cuba and implemented just a few solutions, ever so slowly ("We have no right to make mistakes" he said recently).

While both governments largely eschewed hyperbolic, confrontational rhetoric, and restarted migration talks suspended by the Bush administration, underlying causes of bilateral tensions continued to fester, including Cuban government supporters' harassment of dissidents (which, whether the Cuban government thinks it's our business or not, the U.S. considers to be its business on principle), and the U.S. government's careless continuation of USAID democracy-building programs expanded under the Bush administration. By the close of Barack Obama's first year and Raul Castro's second year in their respective offices, bilateral relations were headed south, with an American citizen in a Cuban jail, apparently after traveling to Cuba as a tourist, but working on a U.S. government contract.

Given these tales I've just retold, it surprises me that I actually think that the stars could yet align in these dog days of summer 2010. And if they do, we might all have the Cuban Catholic Church to thank for its role in triggering a series of events this summer that offer renewed hope of progress in Cuba and the United States. Consider that Raul Castro's government -- as part of an ongoing dialogue with Church leaders -- has released 25 dissidents jailed under Fidel Castro in 2003. (The Church, which has helped broker space for the Ladies in White's marches in Havana, also seems to have played a role in ending the intimidation of the mother of the Cuban prisoner who died after a hunger strike back in February, who led a march in her son's honor yesterday). And note that this summer Fidel Castro began a series of seemingly random public appearances just as the releases began, but said not one word about the dissidents or about the domestic economic restructuring being discussed under his brother's direction.

At the same time, the U.S. Congress has been flexing its muscles vis a vis Cuba travel restrictions, and even passed a bill out of a key House committee this summer, and the Obama administration is now even said to be getting into the game. (Cuba's Catholic Cardinal Jaime Ortega, who has met personally with Raul Castro, even traveled to Washington this summer and met with President Obama's National Security Advisor.) Depending on how ambitious the Obama Administration's expected rule changes turn out to be, they could in turn motivate Congress to finish the job and lift travel restrictions for all Americans when it returns from summer campaigning next month.

And now, New Mexico Governor Bill Richardson is back in Cuba for the week on a follow up to his trade mission to the island last year. Now, I'm sure New Mexico must have something to sell to Cuba, but but it's hard not to speculate that this trip could somehow result in the release of Alan Gross, the American in Cuban jail since December 2009. Afterall, Bill Richardson is known for forays into the most inhospitable environments to negotiate prisoner releases. (Of course, if Richardson manages this trip the way he did the last one, arguably playing more to Little Havana than to Havana, the chances dim considerably.) But if the Cuban government manages to do what the two governments have failed at for many years -- to seize the right moment -- and it releases Mr. Gross in the next few weeks, that would certainly offer tremendous momentum to Congress, which has just enough time left before the fall elections to take a vote on a bill that would lift the travel ban and boost U.S. farm exports to the island.

A lot can, and often does, go wrong, when it comes to the United States and Cuba. And yet, here in Washington, hope, however improbable, springs eternal.