Mr. Gross is innocent, and his continued detention is unjust,” read a memo the United States Agency for International Development sent to the Senate Committee on Foreign Relations in 2010.

At the time, the committee was chaired by Senator John Kerry. Congressman Howard Berman was chairman of the House Committee on Foreign Relations. The two Democrats had been pressing USAID to justify its programs in Cuba, where, flush with funding from the George W. Bush administration, the agency appeared to be running amok.

USAID had a lot to explain.

Alan Gross, who received almost $600,000 in USAID funds, had been arrested in Havana’s José Martí Airport in December 2009, at the end of his fifth trip to Cuba. He was caught smuggling banned electronic communication devices into Cuba, which he installed in synagogues. He was charged with “criminal acts against the independence of the Cuban nation” and was sentenced to 15 years in prison.

Gross was freed by Cuban President Raúl Castro in December 2014, a precondition to President Barack Obama’s agreement to normalize diplomatic relations with Cuba. Gross’s release from prison on the second day of Hanukkah was immediately followed by the president’s announcement of a new U.S.-Cuba policy.

Gross is a small but important part of a larger story.

In 2010, two years into Obama’s first term, USAID bureaucrats were invested in Bush administration policy in Cuba, where tens of millions of dollars flowed to programs funded through a provision in the Helms-Burton Act. Passed in 1996, Helms-Burton wrote the Cuban embargo into law and required that Fidel and Raúl Castro be removed from power before the U.S. would consider Cuba “in transition to democracy.”

John Kerry and Howard Berman, along with other Democrats in Congress, considered the hard-right Cuba policy a waste of money and a strategic failure.

When Gross was detained in December 2009, he was in possession of not only his computer but of several flash drives which included detailed descriptions of USAID programs and protocols in Cuba.

“Since the Helms-Burton Act became law, we have spent more than $150 million on political initiatives in Cuba with nothing to show for it. Our Interests Section in Havana itself, for example, said that there is little evidence these programs have helped the dissidents gain significant support inside Cuba,” Kerry and Berman wrote in a joint letter to Secretary of State Hillary Clinton and USAID Director Rajiv Shah in December 2010. (Shah announced his February resignation just before Alan Gross was released.)

“Fifty years of evidence shows that a pressure-cooker approach aimed at driving rapid, if explosive and violent, change in Cuba—ignoring the Cuban people’s desire for peaceful change—will fail.”

There, in two paragraphs, is the germ of what would become Obama’s policy of apertura with Cuba—even if it took him a while to get there. But before the president could get there, he had to resolve the Alan Gross problem—a vestige of a George W. Bush policy based on further isolating Castro’s Cuba while pouring money into programs to destabilize the regime from within.

Congress had actually authorized $205 million in Cuba-program funding since it passed the Helms-Burton Act, according to a Government Accountability Office report.

Funding for the sort of USAID program that Gross was running in Cuba increased from $3.5 million to $45 million during Bush’s eight years in office. Under Obama, the then-Democratic Congress cut funding in half, but the Bush dollars were still in the pipeline.

Because the USAID Cuba operations are cloaked in secrecy, members of Congress had no idea what they were getting for their money. That is, until the Cuban government convicted Gross, whose clandestine program to set up internet sites designed to evade monitoring by the Cuban government reads like a script from the old spy spoof “Get Smart.”

Insult to Debacle

The work of Alan Gross and his collaborators in Cuba involved secret meetings with rabbis and leaders of Masonic temples.

Gross used unwitting members of American Jewish humanitarian delegations as mules to smuggle electronics—illegal in Cuba—in their luggage.

He put the leaders of Jewish congregations in Cuba at risk by luring them into collaboration under the pretext that he was a humanitarian worker interested in improving internet access for Cuba’s Jews.

Cuban intelligence services were onto Gross as early as 2004, when for a meager $400, Gross carried a package of electronics equipment and money to Cuba for Marc Wachtenheim, another USAID subcontractor. Both men were unaware that the man to whom Gross handed the package was a veteran Cuban undercover intelligence operative known as Agente Gerardo.

When Gross was ultimately detained in December 2009, on his fifth trip to the island, he was in possession of not only his computer but of several flash drives that included detailed descriptions of USAID programs and protocols in Cuba.

Among items Gross smuggled into Cuba were BGAN satellite links, which would allow WI-FI hotspots Gross was setting up to circumvent government servers. A more problematic contraband item was a mobile-phone chip that experts say is often used by the Pentagon and the CIA to make satellite signals virtually impossible to track, according to the Associated Press.

For these services, Gross’s firm was paid $585,000, which does not include costs incurred by Development Alternatives Incorporated, the large contractor that took Gross on as a subcontractor. DAI, with offices in Bethesda, Maryland, and London, continues to be a recipient of lucrative USAID contracts ($300 million in 2012).

To add insult to diplomatic debacle, before Gross went on trial, the Cuban government was broadcasting a series of videos (available on Vimeo) entitled “Las Razones de Cuba,” featuring José Manuel Collera Vento, (a.k.a. “Agente Gerardo”) and another Cuban agent with whom Gross and Wachtenheim had worked but were unaware that their presumed collaborators were stringing them along.

Not the Perfect Agent

Alan Gross was hardly the perfect undercover operative. He didn’t speak Spanish and wasn’t a Cuba expert. According to a “Bring Alan Home” website, he had previously worked on development projects is Azerbaijan, Bulgaria, and the West Bank.

During the Bush administration, Gross decided to take his talents to Cuba and he began looking for a buyer for what he was selling. On one of the flash drives Cuban authorities confiscated when they arrested Gross was a proposal to set up internet sites in Cuban synagogues, which Gross had pitched to Wachtenheim in 2005.

Alan Gross was not the perfect clandestine operative. He didn’t speak Spanish and wasn’t a Cuba expert.

Wachtenheim, a right-wing operative and occasional academic who directed another USAID contractor, the Pan American Development Fund, wasn’t interested. Gross made the same pitch to DAI, according to Cuban authorities who found both of Gross’s proposals on his flash drive.

Cuban intelligence services, however, didn’t need to read Gross’s flash drive to know what he was up to. Agents had penetrated Wachtenheim’s, and subsequently Gross’s, hustle before the two men began their work in Cuba. In 2001, Wachtenheim brought Collera to Washington to meet with Otto Reich at his State Department office.

Reich is a Cuban-born American involved in Latin American skullduggery since the 1980s when, according to a House-Senate Committee deposition, he was a State Department operative planting propaganda stories in the Latin American press during what turned into the Iran-Contra Scandal. Twenty years later, George W. Bush used a recess appointment to name Reich assistant secretary of state for the Western Hemisphere. Wachtenheim recognized Reich as a kindred spirit when Wachtenheim approached him with a never-realized plan to use Masonic lodges as secret internet sites on the island. Agente Gerardo had been the Grand Master of the Grand Masonic Lodge in Cuba.

The two anti-Castro zealots were unaware that Collera had been an undercover Cuban intelligence agent for more than 25 years. Their 2001 meeting is documented in Cuban court filings, and Collera describes it in an extended TV interview he did with a Cuban news outlet. (Reich and Wachtenheim did not return phone calls.)

Foreign service officers at the U.S. Interests Section in Havana knew that Collera was a double agent taking orders “from the Castro regime”—according to a State Department cable posted on WikiLeaks. But USAID contractors, as it turned out, didn’t communicate with the Interests Section.

American Jewish Mules

Gross, a reform Jew, reached out to American Jewish organizations sponsoring humanitarian missions to find “mules” to carry contraband into Cuba. Susan Andisman, of the Jewish Federation of Broward County (Florida), was named in the Cuban government’s sentencia (an indictment and finding of fact). As was Richard Klein, a New Yorker and executive at the Jewish Federation of North America. Both carried electronics equipment through the same Havana airport where Gross was arrested. Gross was aware of the danger associated with carrying contraband, describing his enterprise, in documents obtained by the Associated Press, as “risky business.”

On one occasion in January 2010, after Gross was detained, a USAID official was evidently anxious about the agency’s use of “mules,” sending the following message to agency’s Cuba program staff (in an email obtained by The Washington Spectator):

If you knew that the risks associated with sending travelers to the island were high, would your travelers still want to go? Why or why not?

Please complete the attached table and return it to me by COB Thursday 21 January. You will note that we are not asking you for the travelers’ names. We are also not asking for information about mulas. We’re interested in programmatic travellers who spent time on the island.

Gross’s “mulas” had no idea they were carrying illegal contraband in their luggage.

Cuban intelligence did.

Beyond putting his American “mulas” at risk, Gross risked upsetting the delicate equilibrium between the Castro regime and Cuba’s Jews, who enjoy freedoms many other Cubans do not.

“We have achieved a modus vivendi with the Cuban government,” Arturo Lopez-Levy, former secretary of Cuba’s B’nai B’rith Maimonides Lodge, told The Jewish Daily Forward. “We have freedom of religion, birthright trips. Why do we have to risk our status for this?”

“Cuban Jews had access to the internet for years before Gross started working with them,” a congressional aide who asked that his name not be used told me. “He used the Jewish community for cover. I would also say he was in over his head and [USAID] was operating outside the mandate of its mission.”

The 18-page sentencia released by a Cuban court on March 11, 2011, describes one incident in which Gross failed to tell Jewish community leaders in Havana that he was installing wireless equipment in their synagogues, even though collaborating with an agent of the U.S. government could have landed them in jail.

So there are no heroes in this story. Only villains and a cabal of duped ideologues. Yet bungling secret agent Alan Gross might end up a change agent.

Leaders from synagogues in Havana, Santiago and Camagüey were witnesses for the state in the Cuban government’s prosecution of Gross.

It’s not as if the Cubans cracked a sophisticated spy ring when they busted Alan Gross. He was low-hanging fruit for an intelligence agency essential to a repressive regime that was justifiably paranoid about its powerful neighbor 90 miles to the north and obsessed with suppressing dissent at home.

USAID operatives on the island were no match for the Castro brothers’ sophisticated intelligence service. Included in one Cuban propaganda program is a surveillance video clip of Wachtenheim speaking to Collera several days before Gross was arrested: photographic documentation of a U.S. operative burning his way through USAID grant money and unaware that his Cuban collaborator is Agente Gerardo.

Change Agent?

So there are no heroes in this story. Only villains and a cabal of duped ideologues.

And losers: U.S. taxpayers picking up the tab for USAID contractors on the make.

And the Cuban people, for whom the American counterrevolution has been counterproductive.

Yet bungling secret agent Alan Gross might end up a change agent.

His (deftly negotiated) release by Raúl Castro created the political space for President Obama to announce a U.S.-Cuba policy that is a radical departure from what has been in place since Fidel Castro overthrew Fulgencio Batista in 1959.

The policy will now be tested in Congress, where Florida Republicans Marco Rubio in the Senate and Ileana Ros-Lehtinen in the House lead a Republican Cuba Libre caucus resolved to keep the heat on the regime until both Castro brothers are dead or in exile.

Lou Dubose is the editor of The Washington Spectator.