It would be an oversimplification to claim that the fate of our Cuba and Iran policies are linked. They are two distinct countries in disparate parts of the world, with their own cultures, histories, and governments. Having provided that disclaimer, one does not have to search far in order to find significant overlap in U.S. foreign policy approach towards both nations. Both Cuba and Iran lived under American sponsored dictatorships before populist, anti-American revolutions eventually overthrew them. The aftermath of these revolutions led to authoritarian governments, and a decades long policy by the United States and the international community to isolate, delegitimize, and eventually collapse them.

The similarities do not end there. Both were, until recently, run by leaders (Mahmoud Ahmedinejad and Fidel Castro) hostile to economic or political reform with strong personal ties to the ideological revolutions that brought the current system to power. Both have major elements of the existing political hierarchy (the mullahs in Iran and the military in Cuba) deeply suspicious about the prospects of reform and rapprochement and a vested interest in maintaining the status quo.

Beyond that, the stars have aligned to provide a brief window of opportunity, with leaders in place on all sides open to the prospects of easing tensions and rolling back economic sanctions. While this seems like a depressingly low bar to set for foreign relations, it represents the first and perhaps only such opportunity since the current regimes came to power in the 1950’s and 1970’s. There is one substantial difference: Cuba is a tiny nation that for decades drew its power and resources from its status as a client state of the now long-defunct Soviet Union.

Iran, on the other hand, has the world’s eighth largest active standing army, the ninth largest active military reserves, the fourth largest standing naval force, and a nuclear program that by most accounts can quickly ramp up uranium enrichment past the 20% and 5% limits currently imposed. The increased IAEA inspections that confirm these numbers are part of the current P5+1 negotiating framework.

As a result, even if both nations are subject to the same ineffective policies, there will almost assuredly be more resistance to a deal that legitimizes Iran or its ruling government than a similar deal with Cuba. So it seems that there may be strategic timing to the Obama administration’s announcement lifting some travel restrictions and economic sanctions on Cuba. For the first time in nearly sixty years the U.S. will open up a diplomatic embassy in Havana and the hopes are that continued dialogue will help accelerate economic reforms and potentially end the most harmful aspect of this policy, the embargo that makes international trade and commerce to and from the island difficult if not impossible.

The Futility of Sanctions

If these efforts succeed and lead to tangible reforms within the Cuban government, it will provide a real-time shield and talking point in favor of the administration’s ongoing nuclear negotiations with Iran. The prevailing arguments against engagement with Cuba and Iran are nearly identical: diplomatic overtures are pointless, counterproductive (or worse, naïve), and only serve to legitimize and “reward” bad actors and regimes. The only means to productive and peaceful relations is through regime change and the most effective means to implement change is through isolation and internationally imposed economic devastation. In the case of Iran, hawks will frequently toss “military strikes” and “invasion” onto the list of options.

That these strategies have utterly failed to achieve their stated objectives is self-evident, unless one subscribes to the theory that a half-century is not sufficient time to see the fruits of a policy’s labor. Both the Castro government and the Iranian quasi-theocracy have survived, if not exactly thrived, in the face of this approach. According to a 1997 study by political scientist Robert Pape, this is because while sanctions can be useful tools in economic or trade disputes, when it comes to achieving larger, more ambitious foreign policy goals (such as regime change or political/economic reform) they are startlingly ineffective. The most optimistic assessment of the success of this approach comes from a 1983 study that purported to show economic sanctions were successful in achieving non-economic foreign policy goals in approximately 34% of cases.

While that may not seem impressive, that success rate was significantly higher than previously thought, and the study helped pave the way for the approval or augmentation of sanctions around the world, including Cuba and Iran. What Pape found when he looked into the data was different. Nearly half of the cases deemed “successful” in achieving regime change or political reform involved direct or indirect military action. The other half consisted of examples that either did not qualify as economic sanctions or did not actually lead to the target country making the desired concessions. In all, the study found that of the 115 cases cited in the paper, just five were actual examples of a nation leveraging economic sanctions to achieve larger political goals.

The reason for the failure stems (not surprisingly) from a lack of understanding about the effects sanctions will have on the behavior of the target country. The assumption from policymakers is “that greater cooperation will increase the economic punishment on target states, and, more critically, that increased punishment will make targets more likely to concede.” This is more or less the philosophical underpinning of our strategies towards Cuba and Iran.

After reexamining the data around sanctions, Pape’s thoughts on this mindset are conclusive: “Most modern states, however, resist external pressure. Pervasive nationalism often makes states and societies willing to endure considerable punishment rather than abandon what are seen as the interests of the nation, making even weak or disorganized states unwilling to bend to the demands of foreigners.” The ability of modern states to shift the economic burden of these sanctions to their own people also creates a perverse dynamic, whereby the ruling regime can continue to operate in a state of near luxury while avoiding the blame for economic conditions brought upon their people by “evil foreigners.”

A Willing Partner

Having determined that isolation and sanctions will not lead to the overthrow of the government, the Obama administration has opted for engagement. In Cuba, the U.S. may have found a willing partner from the most unlikely of sources. For decades, Raul Castro had served as a loyal lieutenant to his brother Fidel since the pair helped overthrow Fulgencia Batista’s military junta in the 1950’s. Still, there are signs that he may lack the ideological zeal of his brother, in substance if not in style. In the 1990’s, Fidel was publicly acknowledging and endorsing a latent purge of 30,000 of his poorest citizens from Cuban society. Chafing under extreme economic crisis after the collapse of their Soviet sponsors and the Helms-Burnsley Act (which applied U.S.-based sanctions on doing business with Cuba to foreign companies), the economic effects of the embargo and sanctions caused the Cuban government to entertain the most incremental of capitalist reforms as desperate means for survival.

During that same time, Raul was implementing market-based reforms within the Cuban government as defense minister, creating the kind of bonus incentives programs for his underlings that you might find in any western corporation or company. His methods, which came to be known as “entrepreneurial improvement,” rapidly spread to other sectors of the government-controlled economy.

For a while, it appeared that additional practical economic reforms and the development of private businesses and industries within Cuban society were inevitable. However, as the economy steadily improved in the 2000’s, Fidel no longer felt the same pressure to deviate from the centrally controlled approach that went hand in hand with his communist ideology, and many of these modest steps were reversed or quietly shelved. As his successor, Raul Castro has publicly endorsed his brother’s approach while quietly overseeing the development of private small business industries in the restaurant, housing, and auto industries. While no one should entertain any delusions that Raul will turn his back on the revolution and usher in an age of Cuban capitalism, there is realistic hope that he may build a bridge for the next generation of Cuban leaders to do so.

By publicly announcing that he will step down in 2018 and name a successor, Raul has already acknowledged that the reign of the Castro brothers is nearing an end. What comes next is anyone’s guess, but the deal with the Obama administration appears to be an implicit and long overdue admission that Cuba’s Cold War political structure is badly outdated and ill suited for the modern world.

In Tehran, the election of moderate Hassan Rouhani to the presidency reflected a deep dissatisfaction among Iranian society with Ahmadinejad and the status quo. While Iran’s nuclear program remains popular, the constant antagonism throughout the Bush-Ahmadinejad years appears to have exhausted both sides particularly the younger generations less invested in the historical nature of the conflict and without the scars of the Iranian hostage crisis. Shortly after Rouhani’s election in 2013, Iranian author and expatriate Ardavan Amir-Aslani described the mindset of the under 30 population that makes up 70 percent of Iranian society in an interview for a French news outlet: “They are educated, they personify Iranian civilization, they are connected to the world, they want another way of life, they want to be open to the world and they want to be back on the international scene.”

There is no path back to the international scene without a successful resolution to the nuclear standoff. This is a fact Rouhani understands well, since he served for two years as the chief nuclear negotiator for his country in the early 2000’s. In this role he made moderate headway, suspending enrichment on nuclear material in order to avoid UN sanctions before the election of Ahmadinjad in 2005 led to his ouster. Back in power, he must still contend with the Supreme Leader Ayatollah Khamenei and the mullahs that will likely have final say over any agreement he manages to reach with the West.

A Test Run

Ultimately, talks between Tehran and Washington may fall on its own merit. There are powerful forces aligned against them, at home and abroad. Israel is likely to reject any deal short of complete dismantling of Iran’s nuclear program, peaceful or otherwise. Sunni majority allies like Saudi Arabia are certainly not rooting for a U.S./Iran reawakening. Both Iran and the United States are currently enmeshed in a dozen foreign policy situations across the Middle East that could blow up at any moment and erase any goodwill that has been built up thus far. A good example of this would be the rebel uprising in Yemen, where Iranian-backed revolutionaries overthrew staunch U.S. ally President Abed Rabbo Mansour Hadi. And this is all before you start to consider Congress.

While the previous two extensions signaled that there continues to be real and genuine desire on both sides for an eventual breakthrough, the lack of a framework agreement by the end of 2014 has put the fate of any deal in dire straights. It may have been possible to sell such a deal (lifting sanctions and opening up diplomatic channels in exchange for a right to peacefully enrich and inspections) to a Harry Reid controlled Senate. It would have been a bitter fight that would not split along traditional party lines and the deal could still have been scuttled in the end. Reid was by most accounts dealing with a near veto-proof majority in favor of imposing new sanctions on Iran and more than a dozen Senators in his own caucus co-sponsored legislation to that effect in 2014.

There is virtually zero chance that a deal along those lines would be acceptable to the Senate in its current form, and it seems likely that a united Republican caucus would be able to pick off the 12-13 Democratic Senators required to overcome a presidential veto for either a renewed round of sanctions or some other mischief that would almost assuredly submarine any pending framework for a deal.

However, there may be another way to shift the dynamic onto more favorable terrain for reformers. If the U.S. and Cuba can continue to make progress by trading incremental economic or political reforms in exchange for commensurate sanctions and trade relief, the Obama administration can steadily begin to knock out the legs from what has become the most powerful rhetorical argument against engagement with Iran. If diplomacy and rapprochement lead to quid pro quo and not increased aggression or duplicity on the part of the Castro regime, it will become more difficult for hardliners on both sides of the negotiating table to attack the credibility or intentions of those seeking to make a deal.

After all, if a few years of diplomacy can prove more effective at getting tangible results than half a century of isolation and antagonism, why on Earth would anyone support the latter?