Old soldiers do die, it turns out, but there’s something incongruous about watching ruthless, formerly swashbuckling military dictators end their lives quietly as frail old men in hospital beds.

It happened to Augusto Pinochet, the Chilean strongman, who returned home and died under house arrest in 2006, at 91. Fidel Castro slowly faded from view, becoming even less coherent, before dying at home in November, as his brother slowly rolled back their revolution. And now Manuel Noriega, the former Panamanian leader, has died at 83 following complications from surgery to remove a brain tumor. He had been imprisoned in his home country.

Like nearly every Latin American leader of the late 20th century, but more intensely than most of them, the three men had complicated histories with the United States, the dominant power in the hemisphere: Pinochet as American ally, Castro as nemesis, and Noriega, ultimately, as both. The tale of American involvement with Noriega, and what came afterward, suggests humbling lessons about U.S. ability to change the course of history in its southern neighbors.

For most of his career, Noriega was an exemplar of a certain kind of American intervention in Latin America: The lawless, vicious leader whom the U.S. cultivated and propped up despite clear and serious flaws. Noriega got involved with the U.S. at a young age, volunteering to inform on leftist students during the Eisenhower administration. He later attend the U.S Army School of the Americas, a training center in Panama that was run by the American military that produced an impressive dishonor roll of despots and murderers across Latin America, as part of a U.S. effort to train domestic resistance to leftist politics in the region. Noriega began receiving payments from the CIA in 1971.

A coup in 1968 brought the military to power in Panama, and Noriega rose to become intelligence chief under General Omar Torrijos, a fellow School of the Americas alumnus who signed the agreement conveying the Panama Canal Zone over from American to Panamanian control. In 1981, Torrijos died in a mysterious plane crash, which an estranged Noriega aide later claimed was Noriega’s doing. By 1983, Noriega effectively controlled Panama.

In 1984, Noriega flirted with democracy, but when it appeared that an opposition party would win, he rigged the result, installing Nicolas Ardito Barletta as president. In 1985, Hugo Spadafora, an outspoken Noriega critic, was tortured and killed. Amid accusations that Noriega was behind Spadafora’s death, Barletta promised an investigation. Noriega promptly forced him to resign, installing a more compliant figurehead.

These abuses did not trouble U.S. policymakers, at least not publicly. That’s because Noriega remained an important American partner in Latin America. During the Iran-Contra affair, in which the Reagan administration illegally sold weapons to Iran, funneling the proceeds to the right-wing Contras in Nicaragua, it emerged that Noriega had offered to conduct raids against the leftist Sandinistas. Besides, the U.S. had already shown strong tolerance for antics from Noriega. In 1976, CIA Director George H.W. Bush learned that Noriega had managed to penetrate an American operation spying on him—and was bribing American soldiers to provide tapes. The double-cross was particularly notable because Noriega was still receiving payments from the CIA. Some intelligence officials wanted Bush to press for prosecution of the soldiers, which would have uncovered Noriega’s role, but he declined.

American intelligence officials also knew that Noriega was likely involved in drug smuggling at the time, but they overlooked it because of what they saw as positive benefits of his presence. In fact, even before Noriega’s accession to power, intelligence officials had identified Panama as an essential hub of drug trafficking and laundering of U.S. dollars.

In 1986, however, things began to change. In The New York Times, the legendary investigative reporter Seymour Hersh wrote,The army commander of Panama, a country vital to United States interests in Latin America, is extensively involved in illicit money laundering and drug activities and has provided a Latin American guerrilla group with arms, according to evidence collected by American intelligence agencies.” Officials told Hersh they “had overlooked General Noriega’s illegal activities because of his cooperation with American intelligence and his willingness to permit the American military extensive leeway to operate in Panama.” Noriega was still receiving payments from the CIA at the time.

The following year, former Noriega aide Colonel Roberto Herrera came forth with a series of allegations: that Noriega had conspired to kill Torrijos (Herrera’s cousin); that he had rigged the 1984 election; that he had Spadafora killed. Noriega was also accused of being involved in the killings of other political opponents. Protests broke out in Panama.

Thus began the second phase of American intervention with regard to Noriega: the attempt to push him from power. U.S. officials had already begun trying to pressure Noriega to step down from power when, in January 1988, the U.S. Department of Justice indicted Noriega for his role in the drug trade.

Overall, the U.S. effort to force Noriega out was a disaster. The State Department didn’t know about the indictments until just before they arrived, but they expected the indictments would weaken Noriega. The Treasury Department, assigned to institute sanctions against Noriega, doubted they would weaken him, a perspective that proved prescient. State wanted to remove Noriega by force, while the Defense Department opposed that. (That battle spilled into the newspapers, with the former chairman of the Joint Chiefs of Staff assailing Elliott Abrams, then the top Latin America official at State, for his hawkishness in a letter to the editor.)

In December 1988, a Senate report found that “Noriega had turned Panama’s political system into what witness termed a ‘narcokleptocracy,’ a system in which the Panamanian government became controlled by personal loyalties to Noriega, cemented by graft and corruption, and substantially funded with narcotics money.” This was hardly a secret in Washington, the report said: “By the time General Noriega was indicted, the United States government had received substantial information about the criminal involvement of top Panamanian officials for nearly twenty years and done little to respond.”

It was finally George H.W. Bush, by then president, who moved to topple Noriega. In late December 1989, after two failed coups against Noriega in the course of less than two years, and after Panamanian forces shot and killed a Marine officer in Panama City, Bush ordered an invasion. Nearly 28,000 U.S. troops swarmed into Panama, and the invasion was an almost immediate military success. Twenty-three Americans died.

Yet perhaps the most memorable aspect of the invasion was the most slapstick. Noriega tried to flee, pursued by U.S. special operators. (The manhunt was called “Operation Nifty Package,” a moniker that could have been coined by Dana Carvey’s Bush impersonation.) After four days, Noriega turned up at the Vatican’s embassy in Panama City, initiating a Pythonesque sequence. The U.S. pressured the pope to have Noriega turned over. Meanwhile, American forces encircled the embassy, and based on reports that Noriega was an opera lover who despised rock ’n’ roll, began blaring loud music. The playlist included some bad period rock (redundant, yes, but: Styx, Judas Priest, Sabbath, Twisted Sister), some groaner jokes (Van Halen’s “Panama,” Tom Petty’s “Refugee,” Bon Jovi’s “Dead or Alive”) and, amusingly, the leftist singer-songwriter Bruce Cockburn’s “If I Had a Rocket Launcher.” (There’s no word on whether Noriega was more approving of rap, though rappers found him to be a potent symbol, from Rick Ross, who invoked his name, to the emcee who borrowed in wholesale, calling himself “Noreaga.”)

Finally, after days of refusing American demands to hand Noriega over, the papal nuncio (a de facto ambassador) convinced Noriega to surrender, which he did on January 3. The toppled leader was brought to the U.S., and tried, beginning in 1992. Noriega tried to defend himself by arguing he was acting under CIA auspices, while the government tried, successfully, to have that defense suppressed. He was convicted and sentenced to 30 years in prison.

Noriega was released after just 17 years thanks to good behavior, getting out in 2007 with time served. He was then promptly extradited to France to face money-laundering charges, and was convicted there. Then Panama requested he be extradited to be jailed on a human-rights-crimes conviction he had received in absentia. He arrived back in his home country in December 2011, 22 years to the month after the coup that toppled him, and was imprisoned until his final illness.

The U.S. proved effective in cultivating Noriega, and, once Washington set its mind to toppling him by force, it accomplished that, too. Sean Naylor wrote in the The Atlantic in 2015 that the hunt for Noriega set the template that the U.S. Joint Special Operations Command has used in Afghanistan and Iraq, as well as in the famous raid that killed Osama bin Laden. But just as those military successes have been paired with political outcomes that are ambiguous at best, it’s interesting to ponder how effective American involvement in Panama proved to be.

Before Noriega came to power, Panama was on the rise as a center for drug trafficking and money laundering. Under Noriega, with tacit U.S. approval, Panama was a corrupt center of drug trafficking and money laundering. What about now?

Panama is certainly a freer, more functional democracy than it was in the Noriega era. (Freedom House’s 2017 rankings put it just a bit behind the U.S.) But then again the U.S. was not concerned about whether Panama was a functioning democracy when it was supporting him, and in fact was expressly willing to look the other way. In a bitter irony, Daniel Ortega, the left-wing Nicaraguan leader whom the U.S. hoped to fight with Noriega’s assistance, has returned to power and seems firmly entrenched, at least for now.

But Panama remains haunted by corruption, money-laundering and, by some accounts, drug-trafficking. The country’s crown economic jewel, the canal, is subject to a Panamax freighter’s worth of corruption investigations and questions about the viability of a huge expansion. The April 2016 release of the tranche of documents known as the “Panama Papers” showed the way that Panama has effectively professionalized money laundering into a highly successful white-collar industry, as the country becomes a magnet for shell companies and other legal fictions designed to shelter money. U.S. officials believe that, unsurprisingly, that system is used by drug traffickers to legitimize their own proceeds. Although the Panamanian government pledged to end illegal activity, appointing a blue-ribbon independent panel, the panel promptly collapsed, with Nobel Prize-winning economist Joseph Stieglitz stepping down and alleging government interference.

This state of affairs—and the ways in which it echoes the situation before the U.S. got involved—might suggest a level of humility, if not outright discouragement, about American ability to project power and effect change in Latin America. And in fact there are signs of growing skepticism. President Obama took a largely reactive approach to Latin America during much of his administration, working as a facilitator rather than a driver of policy. Obama’s most significant move in the region was his decision to re-establish diplomatic ties with Cuba and open up travel—that is, working to dismantle one of the most visible symbols of American soft power in the hemisphere. As the U.S. recedes, China has increasingly asserted itself in the region, and the Monroe Doctrine has receded. To be sure, some Latin American leaders continue to allege American meddling in the region, most notably Venezuela, whose president Nicolas Maduro visited a monument to victims of the U.S. invasion of Panama in 2015 in what was seen as a swipe at Washington.

Donald Trump, despite his differences with Obama, is poised to continue the U.S. retrenchment. His Latin America policy so far has consisted of little more than his pledge to renegotiate NAFTA and to build a wall to prevent illegal immigration from Mexico, Central America, and South America. He has suggested rolling back Obama’s opening with Cuba, though it’s unclear how serious he is, especially given his own business explorations there.

Noriega’s death is not the cause of this shift: It must not have been much consolation for the deposed dictator, who viewed himself as a victim of American aggression and was incarcerated to boot, to watch the U.S. pull back. Nonetheless, his passing is a fitting symbol of an era that looks to be ending.