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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