Sometimes prison time actually does rehabilitate. Or perhaps it was Alan Gross’s December 2014 rescue from a Cuban prison by the patient, quiet diplomacy of the Obama administration.

Gross, a small player in the failed U.S. policy to overthrow Fidel (then Raul) Castro, was a USAID contractor who spent five years in a Cuban prison for engaging in illegal covert activity on the island. (Illegal there and probably illegal in the U.S.)

The American operative working in a Cold War program flush with new funding demanded by President George W. Bush was sprung from prison by Barack Obama.

The Wall Street Journal reported last month that Gross is working for a Miami-based PAC that will fund candidates who support President Obama’s move to normalize relations with Cuba.

Bellow from the Journal:

A political-action committee backing candidates in favor of a U.S.-Cuba policy shift will launch its campaign effort Monday with the help of a notable guest: Alan Gross, the U.S. citizen who spent five years in Cuban prisons.

The committee, called New Cuba PAC, will back candidates who favor reorienting U.S.-Cuba policy, particularly with more trade and travel between the two countries. President Barack Obama took steps to lift financial and travel regulations in December as part of a normalization push, but it will take congressional action to fully lift an embargo and allow for full travel to the island.

As we reported at the time of his release, Gross was both a victim of George W. Bush’s Cuba regime-change policy and a perpetrator of several crimes in Cuba.

Gross, who spoke no Spanish and had no background in Cuban politics or policy, was arrested at the José Martí Airport on his fifth smuggling trip. On the U.S. taxpayer’s tab, he had been installing internet hubs in an attempt to break the Castro brothers’ electronic blockade of foreign websites and internet communication.

Among the items Cuban investigators found in Gross’s contraband were sophisticated encryption systems normally available to only the U.S. Army or the CIA.

An American Jew who belongs to a reform congregation in Maryland, Gross used the Cuba’s Jewish community for cover, working with rabbis and the leaders of several synagogues on the island, who were unaware that he was a U.S. agent. He also used unwitting American Jews engaged in humanitarian work for U.S.-based Jewish charities as “mules” to smuggle electronic devices in their luggage when visiting Cuba.

Gross’s arrest panicked USAID officials, who were aware of what he was doing and of the program’s use of mulas to smuggle contraband. One email the Spectator obtained at the time read:

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 travelers who spent time on the island.

The American Jewish USAID operative working in a Cold War program flush with new funding demanded by President George W. Bush was sprung from prison by a Barack Obama diplomatic initiative that had enlisted the support of Pope Francis.

The president’s “home for Hanukkah” delivery of Gross completely unhinged anti-Castro Republicans, most notably presidential candidates Marco Rubio and Ted Cruz.

It’s going to take more than a couple of chilled Cuba Libres to calm their nerves now that their Cold Warrior has come in from the cold to work on behalf of Obama’s Cuba policy.

—Lou Dubose,
July 3, 2015

Lou Dubose is the editor of The Washington Spectator.