The reactions to Fidel’s death have mostly fallen along predictable lines. There are the expected conservative condemnations of a dictator, and the equally predictable lefty eulogies of a man who defied American power and sought social justice. Liberals attack conservatives for bashing Fidel while giving right wing dictators a pass; conservatives attack liberals for overlooking Fidel’s dismal record when it comes to issues liberals claim to care about, like freedom of expression and gay rights.

But there’s something else to think about: whether you loved Fidel, loathed him, or fell somewhere in between, it was John Paul II who sized him up best. Fidel, the Pope said, was a man of destiny. But his destiny was a tragic one.

In some ways, Fidel has to be accounted a success. He took power in Cuba in 1959; almost 70 years later the island is ruled by his chosen successor. He wanted to assert Cuban independence of the United States; Cuba not only sided with the USSR in the Cold War, but it intervened against U.S. interests in wars in Angola, Ethiopia and the Middle East. He wanted a socialist revolution; he got one. He wanted to break the power of the old Cuban elite; he did. Fidel himself, the island he ruled and the revolution he created became global symbols of resistance to U.S. power and to capitalist order. In all this he succeeded, often brilliantly. The ruler of a small and poor island in the Caribbean succeeded in writing himself into the pages of world history in a way that no other Latin American ruler has ever done.

Yet with all this success, Fidel must ultimately be accounted a failure, and if he was honest with himself, he had to have known it. It is not just that Castro failed as a socialist; his greatest failure was as a Cuban nationalist.

Cuban nationalism is real; Cubans have a deep sense of shared history, culture and destiny. But that nationalism is threatened by the power and the attraction of the Colossus of the North. Cuban nationalists have always feared that North American money, culture, military power and demography would swallow Cuba whole, or reduce it to the condition of Puerto Rico.

Castro wanted above all to strengthen the Cuban nation and to make it independent of the United States. In the beginning at least, socialism was less an end in itself than a means to the end of a Cuba free from American pressure and power.

Driving the pre-Castro elite into exile was part of Castro’s plan. The pre-revolutionary business and political leaders of Cuba, he felt, were tainted and compromised by their association with the United States. They had accepted a quasi-colonial role for Cuba, and as long as they made money from it, were content with a Cuba that was “working for the Yankee dollar”, whether in the sugar cane fields, at the baccarat tables or in the red light district of Havana. Fidel wanted to purge the country of this old, collaborationist elite, and build a new Cuba—strong, self-confident and free.

The economic break with the United States, and the switch from the USA to the USSR as his major trading partner caused enormous dislocation in the Cuban economy in the 1960s, but for Fidel the chance to develop an economy that didn’t revolve around trade and tourism with the U.S. was heaven-sent. By taking the path of socialist development in solidarity with the Soviet Union, Fidel believed he saw the chance to create a strong Cuban economy and industrial base that would make the island truly independent.

It didn’t work, and socialism’s failure in Cuba was even more spectacular and damaging than its failure in other parts of the world. In the USSR itself, and in parts of eastern Europe, socialist economic construction may have taken a harsh human toll and ultimately led to stagnation, but along the way at least it created an industrial base. Nothing of the kind happened in Cuba. As an economic planner, Fidel was one of the great failures of the 20th century. Even by socialist standards, he was a flop. Under Fidel’s dead hand, sugar failed, alternative crops failed, manufacturing failed. The handful of successes, mostly in health care and pharmaceuticals, were real, but fell well short of providing the economic platform Cuba needed. As Fidel lay on his deathbed he had to know that two generations of struggle and sacrifice had failed to build a new Cuban economy.

Lee Kwan Yew, Augusto Pinochet, Francisco Franco, Chiang Kai Shek, Park Chung-he: all of these dictators and authoritarians can mock Fidel Castro. They left their countries better off than they found them, and while many of them committed terrible crimes, they can also point to great accomplishments. Fidel has only the crimes.

Fidel never wanted “normalization” of economic relations with the United States. Normalization would mean the end of his dream. Without barriers, Cuban-Americans in Miami would buy back much of the island from its current owners, re-installing themselves as leaders in the society from which he hoped to banish them forever. Amrerican trade and American tourism would once more become the most important factors in Cuba’s economy, and American cultural and poltiical influence would flow unrestricted across the island on a tide of American media.

The openings Castro allowed, very limited in the Clinton years, wider in the Obama years, were forced on him by economic necessity. The collapse of the Soviet Union in the 1990s forced Castro to allow more remittances from Miami and to open up the island to more tourism to stave off a crisis at home. The collapse of Venezuela in the Obama years has once more driven Cuba to the wall. In the end, Fidel became what he hated most: a failed Latin caudillo, presiding over a corrupt and despairing society, propped up by the Catholic Church and the United States.

Nobody knew this better than Fidel Castro, and he must sometimes have cursed the fate that let him outlive not only the global socialist movement led by the Soviet Union but the regional socialist resurgence led by Venezuela. The failure of the Venezuelan revolution stripped the last shreds of credibility away from Fidel’s socialist dream. Not even a country awash in oil, facing no U.S. trade embargo, can make socialism work in Latin America. And it was the failure of Venezuela, and the loss of the economic subsidies that Chavez lavished on his mentor and inspirer Fidel Castro, that plunged Cuba back into its post-Soviet poverty and forced Fidel to remain silent as his brother Raul accepted the return of American tourists and an American ambassador to Havana.

Fidel leaves a shattered society and a desperately poor country behind him. Cuba is more divided today than it was when he conquered it; it is less able to shape its destiny than it was in 1959, and its future will likely be more closely linked to the United States after his death than before his seizure of power.

Now Cubans, those still on the island and those driven into exile by his intolerance and his mismanagement, must begin to think about building something better on the ashes of Fidel Castro’s hopes. It is important for Americans that they succeed.