In March 2019, Mr. Alay traveled to Moscow, just weeks after leaders of the Catalan independence movement went on trial. Three months later, Mr. Alay went again.

In Russia, according to the intelligence report, Mr. Alay and Mr. Dmitrenko met with several active foreign intelligence officers, as well as Oleg V. Syromolotov, the former chief of counterintelligence for the Federal Security Service, Russia’s domestic intelligence agency, who now oversees counterterrorism as a deputy minister at the Russian foreign ministry.

Mr. Alay denied meeting Mr. Syromolotov and the officers but acknowledged meeting Yevgeny Primakov, the grandson of a famous K.G.B. spymaster, in order to secure an interview with Mr. Puigdemont on an international affairs program he hosted on Kremlin television. Last year, Mr. Primakov was appointed by Mr. Putin to run a Russian cultural agency that, according to European security officials, often serves as a front for intelligence operations.

“Good news from Moscow,” Mr. Alay later texted to Mr. Puigdemont, informing him of Mr. Primakov’s appointment. In another exchange, Mr. Dmitrenko told Mr. Alay that Mr. Primakov’s elevation “puts him in a very good position to activate things between us.”

Mr. Alay also confirmed meeting Andrei Bezrukov, a decorated former officer with Russia’s foreign intelligence service. For more than a decade, Mr. Bezrukov and his wife, Yelena Vavilova, were deep cover operatives living in the United States using the code names Donald Heathfield and Tracey Foley.

It was their story of espionage, arrest and eventual return to Russia in a spy swap that served as a basis for the television series “The Americans.” Mr. Alay appears to have become close with the couple. Working with Mr. Dmitrenko, he spent about three months in the fall of 2020 on a Catalan translation of Ms. Vavilova’s autobiographical novel “The Woman Who Can Keep Secrets,” according to his encrypted correspondence.

Mr. Alay, who is also a college professor and author, said he was invited by Mr. Bezrukov, who now teaches at a Moscow university, to deliver two lectures.

Mr. Alay was accompanied on each of his trips by Mr. Dmitrenko, 33, a Russian businessman who is married to a Catalan woman. Mr. Dmitrenko did not respond to requests for comment. But Spanish authorities have monitored him and in 2019 rejected a citizenship application from him because of his Russian contacts, according to a Spanish Ministry of Justice decision reviewed by The Times.

The decision said Mr. Dmitrenko “receives missions” from Russian intelligence and also “does different jobs” for leaders of Russian organized crime.

A few months after Mr. Alay’s trips to Moscow, Catalonia erupted in protests.

A group calling itself Tsunami Democratic occupied the offices of one of Spain’s largest banks, closed a main highway between France and Spain for two days and orchestrated the takeover of the Barcelona airport, forcing the cancellation of more than a hundred flights.

The group’s origins have remained unclear, but one of the confidential police files stated that Mr. Alay attended a meeting in Geneva, where he and other independence activists finalized plans for Tsunami Democratic’s unveiling.

Three days after Tsunami Democratic occupied the Barcelona airport, two Russians flew from Moscow to Barcelona, the Catalan capital, according to flight records obtained by The Times.

One was Sergei Sumin, whom the intelligence report describes as a colonel in Russia’s Federal Protective Service, which oversees security for Mr. Putin and is not known for activities abroad.

The other was Artyom Lukoyanov, the adopted son of a top adviser to Mr. Putin, one who was deeply involved in Russia’s efforts to support separatists in eastern Ukraine.

According to the intelligence report, Mr. Alay and Mr. Dmitrenko met the two men in Barcelona for a strategy session to discuss the independence movement, though the report offered no other details.

Mr. Alay denied any connection to Tsunami Democratic. He confirmed that he had met with Mr. Sumin and Mr. Lukoyanov at the request of Mr. Dmitrenko, but only to “greet them politely.”

Even as the protests faded, Mr. Puigdemont’s associates remained busy. His lawyer, Mr. Boye, flew to Moscow in February 2020 to meet Vasily Khristoforov, whom Western law enforcement agencies describe as a senior Russian organized crime figure. The goal, according to the report, was to enlist Mr. Khristoforov to help set up a secret funding channel for the independence movement.

In an interview, Mr. Boye acknowledged meeting in Moscow with Mr. Khristoforov, who is wanted in several countries including Spain on suspicion of financial crimes, but said they only discussed matters relating to Mr. Khristoforov’s legal cases.

By late 2020, Mr. Alay’s texts reveal an eagerness to keep his Russian contacts happy. In exchanges with Mr. Puigdemont and Mr. Boye, he said they should avoid any public statements that might anger Moscow, especially about the democracy protests that Russia was helping to disperse violently in Belarus.

Mr. Puigdemont did not always heed the advice, appearing in Brussels with the Belarusian opposition and tweeting his support for the protesters, prompting Mr. Boye to text Mr. Alay that “we will have to tell the Russians that this was just to mislead.”

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France Arrests Former Members of Italian Extremist Group

PARIS — The French police on Wednesday arrested seven former members of Italian left-wing extremist groups who had been convicted of terrorism crimes in Italy decades ago, but were given refuge in France.

A court will now decide if the militants, arrested at the request of the Italian authorities, can be extradited to Italy, a decision that could take several years depending on appeals.

Dozens of Italian leftist extremists were given refuge in France decades ago by the socialist government at the time if they agreed to renounce violence, a move that long poisoned the diplomatic relationship between France and Italy.

The government’s announcement of the arrests on Wednesday signaled an easing of that troubled relationship, with Prime Minister Mario Draghi of Italy and President Emmanuel Macron of France managing to establish closer ties in recent months.

Lotta Continua, which translates as “Continuous Struggle,” was also detained in France. Mr. Pietrostefani was sentenced to 22 years in prison for murdering the police chief of Milan, Luigi Calabresi, in 1972.

François Mitterrand, the former socialist president of France, instituted a policy in the 1980s when he was in office of granting asylum to leftist Italian militants — much to the anger of the Italian government, which requested their extradition — providing they renounced violence and were not wanted in Italy for murder or other “crimes of blood.” Some of the militants, like Mr. Pietrostefani, however, had been implicated in such crimes.

One of the beneficiaries of the so-called Mitterrand Doctrine who was arrested on Wednesday was Marina Petrella, a former Red Brigades member who fled to France in 1993 after being convicted of involvement in several murders.

In 2008, President Nicolas Sarkozy rejected a request from the Italian government to extradite Ms. Petrella, citing humanitarian reasons as her health was deteriorating. The refusal provoked outrage in Italy and revived dormant tensions between the two countries.

The French presidency said in its statement Wednesday that the arrests “fall strictly within the framework of the Mitterrand doctrine, since they are blood crimes.”

In 2019, Matteo Salvini, Italy’s interior minister at the time, said that he would “appeal to the French president to return to Italy some fugitives who do not deserve to drink champagne under the Eiffel Tower, but deserve to rot in jail in Italy.”

strategic alliance with Mr. Macron at the European level and Wednesday’s decision testified to this new working relationship.

Marta Cartabia, Italy’s justice minister, said she met with her French counterpart, Éric Dupond-Moretti, and that he had shown a “particular sensitivity” to the case and “decisive will to cooperate.”

Mr. Dupond-Moretti said he hoped the arrests “will allow Italy to turn a bloody and tearful page of its history after 40 years.”

Benedetta Tobagi, an Italian journalist and daughter of Walter Tobagi, a reporter who was killed in 1980 by a left-wing terrorist brigade, welcomed the decision in an editorial in the Italian daily La Repubblica on Wednesday.

But she added, “the anomaly is not the arrests, but the unreasonable persistence of the Mitterrand doctrine, the fact that it took so many years, and so much effort, to unblock the situation.”

Gaia Pianigiani contributed reporting from Rome.

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