In a previous life one of the US government roles I played was as co-team leader of the OSD/JCS Cuba Task Force. That was a combined team of officials and officers from the US Office of the Secretary of Defense (OSD) and Joint Chiefs of Staff (JCS) tasked with exploring contingency scenarios for Cuba, including refugee flows (then ongoing) as well as possible civil unrest and regime transition scenarios in the wake of the withdrawal of Soviet aid to the island nation and the increasingly geriatric nature of its original leadership. My co-team leader was a Cuban American political appointee, with the idea being that my academic experience studying authoritarian regime transitions and knowledge of the Cuban approach to irregular conflict would be balanced by his sensitivity to the domestic political implications of  any moves we proposed to undertake.
Although I cannot reveal much of what we did, I can say a few things about the process that has now led to a normalisation of diplomatic relations between the US and Cuba.
First, almost everyone in the US government realised that the embargo was a failure. However, the Cuban lobby is on a par with the gun and Israel lobbies when it comes to single issue fixation and willingness to spend money for the cause. This made Cuba a thorny political problem for any US government trying to improve relations with it, as the usual suspects would (and still do) immediately hurl the “soft on communism” and “appeasing dictators” invective as part of their negative electoral campaigning. This placed the issue in the “too hard” basket as far as most politicians were concerned, especially given the myriad of other issues at play and the trade-offs they involved. As a foreign diplomat said in my presence when asked about the US approach to Cuba: “That is a domestic matter, not a diplomatic one.”
Secondly, from the 1980s to the present day, every former Chairman of the Joint Chiefs of Staff and the US Chamber of Commerce have repeatedly called for an end to the embargo and resumption of full diplomatic relations. One would have thought that the weight of conservative military leaders and the leading business organisation in the US would hold some sway, but in fact their views were trumped by the lobbying efforts described above. Episodic attempts have been made to launch US business initiatives in Cuba (for example, in agricultural machinery), but the legal and monetary costs of circumventing the embargo by using off-shore subsidiaries, etc. simply proved too much given the limited nature of the potential returns.
Third, as of the early 1990s the Castro brothers increasingly delegated authority to second generation leaders, who now have been replaced in large measure by third generation revolutionary cadres (people in their 40s and 50s). In fact, both the Cuban exile community as well as the revolutionary leadership have seen the physical decline of the so-called “dinosaurios” (dinosaurs) and their replacement with younger, often more moderate leaders who were not present during the revolution and who therefore do not all have personal scores to settle stemming from it. My co-team leader was second generation and not fuelled by the rabid thirst for revenge exhibited by many of his parent’s generation (some of whom I got the dubious pleasure of meeting). Now that second generation’s children are coming to the fore. This has opened the door for initiatives focused on normalising relations.
But the issue remains complex. The end of the Cold War and fall of the USSR actually reinforced the view in some US policy circles that an embargo could, given the withdrawal of Soviet aid to Cuba, bring the Castro regime to its knees. Â On the other hand, the increase in non-US foreign investment in Cuba after the Cold War (mostly but not exclusively in tourism) was seen by some in the US as making the embargo counter-productive when it came to promoting US business interests in its near abroad. Overlying these views was a persistent belief that Cuba continued to logistically and intellectually support Marxist-Leninist guerrilla groups in Latin America (including those that drug trafficked) as well as rogue regimes such as North Korea, Libya, Syria and Iran (to say nothing of Nicaragua and Venezuela). As a result, foreign policy opinion in the US after the Cold War remained very divided on the question of what to do with Cuba given the embargo and rudimentary diplomatic relations.
Yet given the demographic changes mentioned earlier, the question about Cuba the last twenty years has mostly been one of political timing: when is the opportune moment to make the move towards restoring normality to the bilateral relationship? Conventional wisdom on US presidential politics states that only during second terms can presidents get away with bold foreign policy initiatives, and even then they have to be popular and presiding over a strong economy in order to do so (since voters tend to ignore foreign policy issues when their pockets and bellies are full). However, owing to the perverse ideological evolution of the Republican Party, only Democrats would even contemplate doing so after 1990, which meant that it was left to Clinton or Obama to be bold (recall that Nixon opened the relationship with China and Reagan encouraged glasnost and perestroika, even if both Republican presidents did so for self-interested reasons).
I have little doubt that Clinton would have normalised relations with Cuba in his second term if he had not been hamstrung by the Lewinsky scandal, which helped turn the Elian Gonzalez saga into a Republican battle cry (Elian Gonzalez was a little Cuban boy who washed up on US shores in a raft in which his mother died. After weeks of to- and fro-ing between the US government and exiled members of the boy’s family, he was forcibly repatriated to Cuba to live with his divorced father. Sensing that Clinton was wounded by the Starr investigation into Cigargate, the GOP turned the boy’s ordeal into an anti-communist political circus, which effectively ended the quiet efforts Clinton’s administration had initiated with an eye towards opening up the Cuban relationship).
Now it appears that Obama has seized the moment to undertake a little glasnost of his own, perhaps because he senses that he has little to lose given the disloyal nature of the opposition (which will rant and rail at anything he does), perhaps because the US economy is doing well enough for him to feel immune on some aspects of foreign policy even after the adverse results of the midterm elections, and perhaps because, like gay marriage and medical marijuana, the US public has simply changed its views on Cuba over the years. Â In fact, it is likely a little bit of each, as the GOP and Fake News blowhards may not want to waste political capital on a dead issue that will gain the GOP no electoral traction. As it turns out, with the exception of some posturing clowns like Marco Rubio and the braying jackasses on conservative media outlets, the reaction from the political Right has been fairly muted.
It will be interesting to see what happens in the next few years. Back when I was dealing with Cuba, the word from their side was that everything was negotiable except for two pillars of the revolution: health and education. That is to say, the vaunted Cuban health and educational systems were sacrosanct and could not be touched in any post-Castro environment. Beyond that, market forces could dictate how Cuba would re-insert itself in the global economy. With an extremely literate, healthy and underemployed work force, it would seem that Cuba would be ideal for any number of value-added export commodity production ventures (textiles and pharmaceuticals have already become targets of foreign investor interest).
The other issue, left unresolved during my time working that beat, was the role of the Communist Party. It is clear that the Cuban political elite have been watching the transitions in the former socialist world, be it the USSR, China, Vietnam or Eastern Europe. They have also watched the experiments in indigenous socialism in Venezuela, Ecuador and Bolivia. It is pretty clear that they would prefer to do a China-style transition to state capitalism under one party rule.
The trouble with that preferred picture is that it is only a partial transition, with the political regime remaining largely the same while the economy changes. That may be possible in a huge country like China but is problematic in a small country like Cuba, especially when it is so proximate to a formerly adversarial super power and has a number of expatriates with ideas about Cuba’s future that do not include a dominant role for the Communist Party, much less its continued sole rule.
Thus the conundrum for the second and third generation Cuban Communist Party leadership is whether to embark on a sequential transition (first changing the economy then the political system, or, less likely, vice versa), or  to go all in and mount a simultaneous transition of the economic and political systems. From the standpoint of keeping things peaceful and orderly, the best hope scenario is a sequential transition in which economic change precedes political change. Opening Cuba for business will present a formidable challenge for the Communist Patry, and the social and cultural influences that will come with diplomatic normalisation and economic opening will be hard to contain, much less stop. So whether by design or by the forced pace of change, it is likely that the Cuban political system will open up as a result of the economic transition and its superstructural ramifications.
The key is for the Cuban political elite to realise that the Chinese transition model is not possible for them given the circumstances, and that the days of one party rule will either come to a natural end or be overturned by force. In that light the best thing to do is to prepare a timetable leading up to multiparty competitive elections somewhere down the road, with appropriate guarantees put in place to preserve key revolutionary gains and to safeguard the institutional position of entities like the Revolutionary Armed Forces (FAR). Â That will take some doing, and could well take a fair bit of time given the current makeup of the Communist Party leadership (in which Fidelistas still hold significant influence along with Raulistas).
The question remains as to what will happen with the two pillars of the revolution in a market-driven economy. It also remains to be seen as to how Cuban society will respond to the introduction of full market logics on the island. Things like the elimination of food subsidies and introduction of merit-based employment criteria in and outside the public serve could prove painful for Cuban society. It could also lead to  criminal opportunism in what some observers have already characterized as an increasingly amoral and feral civil society no longer wedded to the revolutionary ethos of the original 26th of July movement. If one thinks of where Cuba is spatially located in relation to drug trafficking corridors, the downside possibilities should be obvious.
Even so, the resumption of full diplomatic relations is a welcome development and hopefully followed by a formal end to the US embargo (not a certain thing, given opposition by GOP majorities in both the Senate and the House of Representatives). There still will be many hard days ahead as Cuba comes to grip with its post-revolutionary future, but at least the range of potential outcomes will be expanded relative to those extant up until a few days ago. As for the US, it demonstrates that sometimes diplomatic face-saving on foreign policy is a waste of energy and the better self-interested choice is to admit mistakes and move on. As the old Korean saying goes: a rich uncle can afford to be generous.
Whatever its motivations, Uncle Sam just was.