No matter the noble intentions of the Cuban revolution, Cuba has been a repressive oligarchy for more than half a century. And no matter the dubious motives behind the US desire for regime change in Cuba, everyone, everywhere should like to see Cubans gain political freedom. And so the question fairly asked is: what should the US be doing to facilitate regime change in Cuba?

The transition from despotism to liberty and democracy has occurred so many times in human history that the formula should by now be common knowledge. Countries as diverse as England, France, the US, South Korea, Singapore and Taiwan have all gone through roughly the same process to get from their illiberal, undemocratic beginnings to the modern states they have since become.

Once liberal policies toward private property and contracts emerge, along with institutions to enforce and maintain them, a country’s economic development accelerates – and within a few generations an ever-greater fraction of the population will rise out of poverty. And as people grow wealthier, they invariably seek a political voice commensurate with their economic power. This storyline was as readily observed in 18th century America as it was in 20th century Singapore.

The lesson learned is that despots can be traded into oblivion. This already is the tacit US policy toward China – that as Chinese industrialists grow more powerful, the oligarchic Communist Party will eventually be unable to contain them. Incidentally, US policy toward China is utterly irreconcilable with its policy toward Cuba. In the days of the Cold War, of course, it could have been argued that enriching a Soviet ally ninety miles off the coast of Florida was dangerous business. However since the demise of the USSR twenty-five years ago, Cuba no longer poses a security threat to the US. According to the same logic that has made China America’s largest trading partner, trade with Cuba today would pose a real threat to the Castro regime, and would be a boon to the cause of Cuban liberty.

No other approach works. Democracy and liberalism imposed from without – as in the case of Iraq and Afghanistan – collapse for lack of the necessary foundation. Isolation – as in the case of North Korea – leaves the regime in control of the economy, reinforcing their power. Trading despots into extinction takes time, but it works, yielding stable, liberal democracies.

Of course despots in Cuba and China have their own motives. In China, an increasingly affluent population is kept docile by rising incomes (and fanatical media censorship!). Cuba’s government would probably also be willing to give up some control over the economy in exchange for economic growth. And once living conditions start improving, and expectations change, despots find themselves locked onto a course that will all but surely drive them from power.

Unfortunately, US policy toward Cuba is driven by a vocal minority, which itself has been unable or unwilling to learn the most obvious lessons from history – including, above all, the extraordinary failure of those policies to alter the status quo in Cuba after more than fifty years. An about-face is long overdue. The Obama administration’s tentative first steps toward building diplomatic and economic ties between the US and Cuba are a step in the right direction.

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