Tallinn, Estonia — When charismatic opposition leader Boris Nemtsov was gunned down on a bridge near the Kremlin in February 2015, more than 50,000 Muscovites expressed their shock and outrage the next day at the brazen assassination. Police stood aside as they rallied and chanted anti-government slogans.

Nine years later, stunned and angry Russians streamed into the streets on the night of Feb. 16, when they heard that popular opposition politician Alexei Navalny had died in prison. But this time, those laying flowers at impromptu memorials in major cities were met by riot police, who arrested and dragged hundreds of them away.

In those intervening years, Vladimir Putin's Russia evolved from a country that tolerated some dissent to one that ruthlessly suppresses it. Arrests, trials and long prison terms — once rare — are commonplace, especially after Moscow invaded Ukraine.

Alongside its political opponents, the Kremlin now also targets rights groups, independent media and other members of civil-society organizations, LGBTQ+ activists and certain religious affiliations.

“Russia is no longer an authoritarian state – it is a totalitarian state,” said Oleg Orlov, co-chair of Memorial, the Russian human rights group focused on political repression. “All these repressions are aimed at suppressing any independent expression about Russia’s political system, about the actions of the authorities, or any independent civil activists.”

A month after making that comment to The Associated Press, the 70-year-old Orlov became one of his group's own statistics: He was handcuffed and hauled out of a courtroom after being convicted of criticizing the military over Ukraine and sentenced to 2½ years in prison.

Memorial estimates there are nearly 680 political prisoners in Russia. Another group, OVD-Info, says that 1,143 people are behind bars on politically motivated charges, with over 400 others receiving other punishment and nearly 300 more under investigation.

The USSR vanishes but repression returns

There was a time after the collapse of the Soviet Union when it seemed Russia had turned a page and widespread repression was a thing of the past, said Orlov, a human rights advocate since the 1980s.

While there were isolated cases in the 1990s under President Boris Yeltsin, Orlov said major crackdowns began slowly after Putin came to power in 2000.

Exiled oil tycoon Mikhail Khodorkovsky, who spent 10 years in prison after challenging Putin, told AP in a recent interview the Kremlin began stifling dissent even before his 2003 arrest. It purged independent TV channel NTV and went after other defiant oligarchs like Vladimir Gusinsky or Boris Berezovsky.

Asked if he thought back then whether the crackdown would reach today's scale of hundreds of political prisoners and prosecutions, Khodorkovsky said: “I rather thought he (Putin) would snap earlier.”

When Nadya Tolokonnikova and her fellow members of Pussy Riot were arrested in 2012 for performing an anti-Putin song in a main Orthodox cathedral in Moscow, their two-year prison sentence came as a shock, she recalled in an interview.

“Back then, it seemed an incredibly (long prison) term. I couldn’t even imagine that I would ever get out,” she said.

A rising intolerance for dissent

When Putin regained the presidency in 2012 after evading term limits by serving four years as prime minister, he was greeted by mass protests. He saw these as Western-inspired and wanted to nip them in the bud, said Tatiana Stanovaya of Carnegie Russia Eurasia Center.

Many were arrested, and over a dozen received up to four years in prison after those protests. But mostly, Stanovaya said, authorities were “creating conditions in which the opposition could not thrive,” rather than dismantling it.

A flurry of laws followed that tightened regulations on protests, gave broad powers to authorities to block websites and surveil users online. They slapped the restrictive label of “foreign agent” on groups to weed out what the Kremlin saw as harmful outside influence fueling dissent.

Navalny in 2013-14 was convicted twice of embezzlement and fraud, but received suspended sentences. His brother was imprisoned in what was seen as a move to pressure the opposition leader.

Moscow's annexation of Crimea in 2014 from Ukraine created a surge of patriotism and boosted Putin’s popularity, emboldening the Kremlin. Authorities restricted foreign-funded nongovernmental organizations and rights groups, outlawing some as “undesirable,” and targeted online critics with prosecutions, fines and occasionally jail.

In the meantime, the tolerance for protests grew thinner. Demonstrations spearheaded by Navalny in 2016-17 brought hundreds of arrests; mass rallies in summer 2019 saw another handful of demonstrators convicted and imprisoned.

The Kremlin used the COVID-19 pandemic in 2020 as an excuse to ban protests. To this day, authorities often refuse to allow rallies, citing “coronavirus restrictions.”

After Navalny's poisoning, recuperation in Germany and arrest upon his return to Russia in 2021, repressions intensified. His entire political infrastructure was outlawed as extremist, exposing his allies and supporters to prosecution.

Open Russia, an opposition group backed from abroad by Khodorkovsky, also had to shut down, and its leader, Andrei Pivovarov, was arrested.

Orlov's group Memorial was shut down by the Supreme Court in 2021, the year before it won the Nobel Peace Prize as the hopeful symbol of a post-Soviet Russia. He recalled the disbelief about the court's ruling.

“We couldn’t imagine all these next stages of the spiral, that the war would erupt, and all those laws about discrediting the army will be adopted," he said.

War and repressive new laws

With the 2022 invasion of Ukraine, Russia enacted those repressive new laws that stifled any anti-war protests and criticism of the military. The number of arrests, criminal cases and trials mushroomed.

Charges varied — from donating money to rights groups helping Ukraine to involvement with Navalny’s now “extremist” group.

Kremlin critics were imprisoned, and their prominence didn’t seem to matter. Navalny eventually got 19 years, while another opposition foe, Vladimir Kara-Murza, got the harshest sentence of 25 years for treason.

Among those also swept up: a St. Petersburg artist who got seven years for replacing supermarket price tags with anti-war slogans; two Moscow poets who got five and seven years over reciting verses in public, one of which mentioned Ukraine; and a 72-year-old woman who got 5½ years for two social media posts against the war.

Activists say prison sentences have gotten longer, compared with those before the war. Increasingly, authorities have appealed convictions that resulted in lighter punishment. In Orlov’s case, prosecutors sought a retrial of his earlier conviction that initially drew only a fine; he later was sentenced to prison.

Another trend is an increase in trials in absentia, said Damir Gainutdinov, head of the Net Freedoms rights group. It counted 243 criminal cases on charges of “spreading false information" about the military, and 88 of them were against people outside Russia — including 20 who were convicted in absentia.

Independent news sites were largely blocked. Many moved their newsrooms abroad, like the independent TV channel Dozhd or Novaya Gazeta, with their work available to Russians via VPNs.

At the same time, the Kremlin expanded a decade-long crackdown against Russia's LGBTQ+ community in what officials said was a fight for “traditional values” espoused by the Russian Orthodox Church in the face of the West’s “degrading” influence. Last year, courts declared the LGBTQ+ “movement” extremist and banned gender transitioning.

Pressure on religious groups continued, too, with hundreds of Jehovah’s Witnesses being prosecuted across Russia since 2017, when the denomination was declared extremist.

The system of oppression is designed “to keep people in fear,” said Nikolay Petrov, visiting researcher at the German Institute for International and Security Affairs.

It doesn't always work. Last week, thousands of people defied scores of riot police to mourn Navalny at his funeral in southeastern Moscow, chanting “No to war!” and “Russia without Putin!” — slogans that normally would result in arrests.

This time, police uncharacteristically did not interfere.

Associated Press writer Emma Burrows contributed.