From PunditWire.com:

Unexpected jolts can quickly unravel authoritarian regimes.  Maybe 2015 will see Cubans responding en masse to the more flexible policy adopted by the Obama Administration, massing in the streets and forcing a showdown with the Castro regime.  If they succeed in breaking the back of the communist system, how might a new democratically elected government start to put things right?

Any new leadership in Cuba will confront five decades of incompetent socialist rule that has turned the country into a staggering failure.  In 1958, Cuba had a per capita GDP of $3,200 — higher than any East Asian country or colony save Japan.     Singapore’s per capita GDP was below Cuba’s, at $2,300.  Singapore’s GDP per capita is now $55,000 while Cuba’s is a pitiful $5,000.  And, yes, Singapore has a fine health care system too.

By now, countless thousands of Cubans have a stake in the old order.  On the day after liberation, bureaucrats, policemen and soldiers will still be there, expecting to be paid.  Murky interests that flourished under the Castro regime – some now greedy to benefit from the easing of U.S. sanctions – will have a powerful interest in manipulating the fledgling democracy.  Many Cubans involved in the outreach of the country’s healthcare arrangements will be wary of radical change.  In short, even with a strong popular mandate, Cuba’s new leaders will have difficulty in managing the expectations (and demands) of sullen or fearful legacy interests from the communist system.

Recent turmoil in the greater Middle East may well make U.S. officials nervous about another revolution 90 miles off the coast of Florida.  But as the Arab upheavals show, a policy of promoting ‘stability’ based on extended authoritarian decay only makes the eventual collapse all the more unmanageable.  In Iraq, the failure of western governments actively to support opponents of Saddam’s regime by planning systematically for a transition to something resembling pluralism has created a grim situation.

Western policy in the Balkans offers one impressive example of how outside powers can help prepare a country for democratic transition.  In 1999 the United Kingdom with the United States and key European partners made a strategic decision to prepare for the end of Serbia’s Milosevic regime.  British officials established in neighboring Budapest a base for post-regime planning and hosted seminars and workshops on practical policy themes: agriculture, water, taxation, education, environment, health, urban planning and so on.  The aim was to work up operational policy dossiers that might help Serbia’s eventual new democratic government get off to a strong start.  Enthusiastic young Serbs themselves took the lead in much of this work.

When Serbian dictator Slobodan Milosevic was ousted in a popular rebellion in 2000, many of these experts went on to become Ministers and senior officials in the transitional government.  The new Serbian system alas could not make a clean break with Serbia’s criminalized political culture or its links to reactionary elements in Moscow.  The 2003 assassination of Serbian Prime Minister Zoran Djindjic dealt Serbia’s reform process a blow from which it has never recovered.  Nevertheless, thanks to this active support for creative practical policy thinking before Milosevic fell, Serbia’s democracy made an impressive start in the right direction.

The United States and its allies should launch a similar process for Cuba.  An allocation of no more than a few millions dollars could establish a Cuba Transformation Initiative, based in a friendly Latin American country, to start planning for a new, democratic Cuba.

This initiative sends all the right signals. It tells the Castro regime elite that their dreary game is up – western governments are now working on the assumption that sooner or later Cuba will have a government chosen through free elections that will build a society based on robust market principles.  It also sends a message to those who will comprise Cuba’s first post-communist leaders: western governments are on your side, and investing in your responsibility and patriotism. These two messages together underscore another message to potential waverers within the communist hierarchy: when the pivotal moment comes and the regime totters, side with the future, not the past.

In Serbia’s case, Milosevic did not care about any such future policy planning; he expected to stay in power indefinitely. The Castro regime of course will do all it can to stop Cubans within Cuba participating in this initiative (though, armed with the Internet, they increasingly will find ingenious ways to contribute anyway).  In the early stages, Cuba’s educated diaspora with experience in democratic values will need to take the lead.

It will not be the job of the Cuba Transformation Initiative to anoint new leaders.  But it can set up policy “baskets” for each Ministry in a plausible new Cuban government and determine how to sequence key economic and social reforms.  It can draft rules for managing and targeting foreign assistance to help ensure that Cubans are not swept aside by the tsunami of well-funded foreign experts that will descend on Cuba when Castroism collapses.  It can draft options for a new democratic constitution and identify fair voting systems that suit Cuba’s geography and traditions.  It can make proposals for dealing with the sprawling communist-era archives, including secret police records. It can tackle difficult moral questions in the transition, drawing on best practice from South Africa, Poland and elsewhere. How should the new government balance reconciliation with human rights, transparency and justice for the regime’s worst elements?

With a strong body of world-class professional analysis and insight already prepared, Cuba’s first democratic government will hit the ground running. Even those who oppose the Obama Administration’s new Cuba policy can agree that the time has come to start hard planning for a democratic transformation in Cuba. A transitional policy planning body, based near Cuba and led by the country’s own professionals and experts in exile, will make a lasting contribution by helping a free Cuba at last move forward strongly and on its own terms.

Author Bios:

Charles Crawford was UK Ambassador in Sarajevo, Belgrade and Warsaw and worked to support democratic transformation in South Africa, Russia, Bosnia and Herzegovina, and Serbia and Montenegro. His ebook Speechwriting for Leaders will be published in early 2015.

Pratik Chougule was a speechwriter at the State Department in the Office of the Under Secretary for Arms Control and International Security.  He has assisted a number of Bush Administration officials with the research and writing of their memoirs.