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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Criminal or Martyr? A Prisoner Poses a Political Dilemma For Spain

BARCELONA — Off a leafy boulevard in Barcelona sit the headquarters of Omnium Cultural, an organization known in Spain as much for its literary prizes as for its dreams of an independent republic in Catalonia.

But its president, Jordi Cuixart, is nowhere to be found: For the last three and a half years, he has lived in a prison cell.

To the Spanish authorities, Mr. Cuixart is a dangerous criminal, convicted of sedition for leading a rally at a time when he and other separatist leaders were seeking to set up a breakaway state in the northeastern region of Catalonia. Yet to his supporters, and in the eyes of many foreign countries, he is a political prisoner sitting in the heart of Europe.

“They want us to change our ideals,” Mr. Cuixart said, speaking through a thick pane of glass in the prison visitors’ section on a recent afternoon.

Mr. Cuixart and eight other men jailed for sedition are now martyrs who, according to human rights groups, are being held for nothing more than voicing and acting on their political views.

For the Spanish government — and for Europe as a whole — they have also become a diplomatic headache, raising accusations of hypocrisy against a region known for demanding greater democratic freedoms around the world.

Russia this year cited the Catalonian inmates to deflect calls from Europe for the release of Aleksei A. Navalny, the Russian opposition leader. The United States lists the prisoners in its human rights report on Spain and calls their jailing a form of political intimidation.

holding Hungary and Poland accountable to E.U. rule-of-law standards, some European parliamentarians noted a double standard: Spain, they said, held political prisoners.

a regional independence referendum in defiance of the Spanish courts. The national government in Madrid sent in riot squads, which seized ballot boxes and even beat some of the voters.

Separatists claimed victory anyway, despite the fact that more than half of voters did not cast ballots and polls showed that Catalonia was split on independence.

Defiant, the Parliament in Catalonia went ahead and declared independence anyway — only to suspend its own declaration before being dissolved by the Spanish government. By that time, Mr. Cuixart had already been arrested and other separatist leaders fled for Belgium.

In 2019, the courts sentenced Mr. Cuixart and eight others to between nine and 13 years in prison after convicting them of sedition.

“He is in jail simply for exercising his right to express himself,” Esteban Beltrán, who heads the Spanish office of Amnesty International, said of Mr. Cuixart.

the terrorist group ETA, which fought for decades for the independence of the northern Basque region.

“They aren’t political prisoners. These are politicians that have broken the law,” Ms. González Laya said in an interview.

“The question is, do you have in Spain the ability to express a different opinion? Answer: Yes. Do you have the right to unilaterally decide that you break up the country? No,” she added.

But David Bondia, an international law professor in Barcelona, said that the Spanish government was considering an overhaul that would weaken its sedition laws, something he sees as an admission that there had been a mistake in jailing the separatist leaders.

Mr. Cuixart’s case was even more problematic from a legal view. He was the head of a cultural group, yet his sedition trial was conducted under a legal framework reserved for politicians, Mr. Bondia said, raising due-process questions.

For Carles Puigdemont, the former president of Catalonia who led the referendum push, the situation recalls the days of the Franco dictatorship, when political opponents lived in fear of persecution.

“For us, this has hit hard and brought us to the past,” he said.

Mr. Puigdemont, who is also wanted on sedition charges, fled Spain in 2017 for Belgium, where he serves in the European Parliament. But his parliamentary immunity was removed in March, allowing for him to be extradited.

approved by voters and the regional Parliament. The move brought widespread anger and separatist flags became common in the countryside.

Soon, Parliament was discussing a move to declare an independent state, long considered a pipe dream of radicals.

Mr. Cuixart, who by 2015 had become the president of Omnium, was sometimes conflicted that his group had also joined the independence push — it was a cultural organization after all, not a political one. But in the end, he said that not joining would have been standing on the wrong side of history.

The crucial day came for Mr. Cuixart on Sept. 20, 2017, when the Spanish police, trying to stop the independence referendum from taking place, had stormed a Catalan regional ministry building on suspicions that plans for the vote were being organized there. But a giant crowd surrounded the location.

Mr. Cuixart and a pro-independence leader, Jordi Sánchez, tried to mediate between the protesters and the police. They set up pathways through the crowd for officers to enter the building and made announcements that anyone considering violence was a “traitor.”

As the night wore on, Mr. Cuixart said that he had feared violent clashes. In a recording, he is seen on top of a vehicle calling for the crowd to disperse. Despite jeers from the protesters, most left and Mr. Cuixart said that he then went to bed.

The vote was held amid the crackdown the next month. But Mr. Cuixart recalled an earlier act of civil disobedience when there were no consequences after he dodged a military draft as a young man. He thought he had little to fear this time around.

But then the charges came: sedition, one of the highest crimes in Spain. Such draconian charges for activity at a protest surprised even legal experts who said that the sedition laws — which cover crimes less serious than full-out rebellion — had been rarely used in a country.

“I had to look up what ‘sedition’ even was,” Mr. Cuixart said.

Mr. Cuixart now spends his days at the Lledoners prison, a penitentiary built for about 1,000 inmates, and home to convicted drug peddlers and murderers. He said he spends his afternoons meditating and writing letters.

Jordi Cañas, a Spanish member of the European Parliament who is against Catalan independence, said he felt little pity for Mr. Cuixart’s situation because the separatists brought it on themselves.

“I don’t forgive them because they’ve broken our society,” Mr. Cañas said, adding that the independence push still divided Spanish homes. “I have friends I no longer speak to over this.”

Mr. Cuixart, for his part, said he was not asking for forgiveness. He would do it all over again, he said. It was Spain that needed to change, he said, not him.

“At some point, Spain is going to have to reflect and ask themselves, ‘What are they going to do with me?’” he said. “Eliminate me? They can’t.”

Leire Ariz Sarasketa contributed reporting from Madrid.

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E.U. Parliament Strips Carles Puigdemont of Immunity

MADRID — The European Parliament has stripped the immunity of Carles Puigdemont, the former separatist leader of Catalonia, clearing the way for Spain to make a fresh attempt to extradite him from Belgium and try him on sedition charges.

The European Parliament said on Tuesday that a majority of its members had voted a day earlier in a secret ballot to remove the immunity of Mr. Puigdemont and two other Catalan members of the assembly who face charges in Spain related to a botched attempt to declare Catalonia’s independence in 2017. Spain’s judiciary has charged that their bid was unconstitutional.

The vote on Monday ended a lengthy battle by Mr. Puigdemont and his colleagues to use their protection as elected members of the European assembly to shield them from prosecution in Spain. Now it is up to the Belgian judiciary to rule on whether Mr. Puigdemont should be sent back to the Spanish capital, Madrid, to stand trial.

“It is a sad day for the European Parliament,” Mr. Puigdemont said. “We have lost our immunity, but the European Parliament has lost more than that and as a result, European democracy too,” he said, adding that this was “a clear case of political prosecution.”

regional elections in Catalonia that increased the majority of pro-independence parties in the regional Parliament. Separatist politicians have held control since 2015, but the secessionist conflict has split Catalan society while also remaining a highly contentious issue in national politics.

ousted his regional government for holding a referendum that Spanish courts had ruled illegal and then declaring Catalonia’s independence.

During the past three years, Mr. Puigdemont has successfully fought off attempts to extradite him both from Belgium and Germany, where he was briefly detained during a trip.

Ioannis Lagos, who was sentenced in Greece last year for his activities with the far-right Golden Dawn party. The Greek government considers Golden Dawn a criminal organization.

The Catalan case has divided politicians in Brussels, many of them loathe to set a precedent of lawmakers being tried over political activity. The removal of Mr. Puigdemont’s immunity was approved by three-fifths of the members of the European Parliament.

It could take months for Belgian courts to rule on Spain’s latest attempt to extradite Mr. Puigdemont and the two other Catalan leaders, Antoni Comín and Clara Ponsatí.

The Brussels Public Prosecutor’s Office is examining the possibility of renewing legal proceedings in Belgium, a spokeswoman for the office said.

Should the Belgian courts block the extradition request, the Catalans would continue to sit in the European Parliament, but without special immunity rights.

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