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Russian Roulette

Russian Roulette

The Inside Story of Putin's War on America and the Election of Donald Trump
4.21
6k+ ratings
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Key Takeaways

1. Russian interference in the 2016 U.S. election was extensive and multifaceted

"The Russians were talking, telling one another, 'great job.' It was pretty specific. They were celebrating their success."

Comprehensive campaign. Russia's interference in the 2016 U.S. election was a sophisticated, multi-pronged effort that went beyond traditional espionage. It included cyberattacks on the Democratic National Committee (DNC) and Clinton campaign, strategic release of hacked emails through WikiLeaks, creation of fake social media accounts and personas, and propaganda efforts through state-owned media outlets like RT and Sputnik.

Motivations and goals. The Russian operation, directed by President Vladimir Putin, aimed to:

  • Undermine public faith in the U.S. democratic process
  • Denigrate Hillary Clinton and harm her electability
  • Boost Donald Trump's chances of winning
  • Sow discord and exacerbate existing divisions in American society

The campaign's scope and audacity surprised many U.S. officials, who later acknowledged it as an intelligence failure and a failure of imagination in recognizing the threat.

2. Trump's business ties to Russia created potential conflicts of interest

"Russia has never tried to use leverage over me. I HAVE NOTHING TO DO WITH RUSSIA - NO DEALS, NO LOANS, NO NOTHING!"

Long-standing connections. Despite Trump's denials, he had pursued business deals in Russia for decades, including attempts to build a Trump Tower in Moscow. These efforts continued even during his presidential campaign, raising questions about potential conflicts of interest and vulnerability to Russian influence.

Key examples:

  • 1987: First trip to Moscow to scout potential hotel sites
  • 2013: Hosted Miss Universe pageant in Moscow, partnering with Aras Agalarov
  • 2015-2016: Pursued Trump Tower Moscow project with Felix Sater as intermediary

Trump's praise for Putin and reluctance to criticize Russia during the campaign raised further concerns about his motivations and potential compromises. His refusal to release tax returns and fully divest from his businesses upon taking office added to the controversy surrounding his Russian connections.

3. The FBI and intelligence community struggled to respond effectively to Russian meddling

"We were facing one big pile of shit. The question was, from which side are you going to eat?"

Challenges and missteps. The FBI and U.S. intelligence agencies faced numerous obstacles in addressing Russian interference:

  • Initial skepticism about the scope and seriousness of the threat
  • Concerns about appearing partisan or influencing the election
  • Difficulty in attributing cyberattacks definitively
  • Bureaucratic infighting and communication breakdowns

Key events:

  • July 2016: FBI opens counterintelligence investigation into Trump campaign-Russia links
  • October 2016: Intelligence community releases statement attributing hacks to Russia
  • January 2017: Intelligence assessment concludes Putin ordered influence campaign

The agencies' handling of the situation, particularly FBI Director James Comey's public statements about the Clinton email investigation while remaining silent on the Trump-Russia probe, would later face intense scrutiny and criticism.

4. WikiLeaks played a crucial role in disseminating hacked Democratic emails

"WikiLeaks has a very big year ahead."

Strategic releases. WikiLeaks, led by Julian Assange, became a key conduit for disseminating emails stolen from the DNC and Clinton campaign chairman John Podesta. The organization's releases were timed for maximum political impact:

  • July 22, 2016: DNC emails released just before Democratic National Convention
  • October 7, 2016: Podesta emails released hours after Access Hollywood tape

Controversial role. WikiLeaks' involvement raised questions about its motivations and potential coordination with Russian intelligence. Assange denied receiving the emails from Russia, but U.S. intelligence concluded that Russian military intelligence used WikiLeaks as a front for its operations.

The email releases dominated news coverage in the final months of the campaign, overshadowing other issues and keeping Clinton on the defensive. The steady drip of revelations contributed to a narrative of Clinton as untrustworthy and the Democratic establishment as corrupt.

5. Social media platforms were weaponized for disinformation campaigns

"We had a goal to set up the Americans against their own government. To cause unrest [and] cause discontent."

Sophisticated operation. Russia's Internet Research Agency (IRA) orchestrated a massive social media influence campaign targeting American voters:

  • Created thousands of fake accounts and pages on Facebook, Twitter, and Instagram
  • Posed as American activists and interest groups
  • Purchased political ads and promoted divisive content
  • Organized real-world events and protests

Scope and impact:

  • 126 million Americans exposed to IRA content on Facebook
  • 1.4 million election-related tweets from Russian-linked accounts
  • $100,000 spent on Facebook ads reaching 5 million people

The social media companies were slow to recognize and respond to the threat, highlighting vulnerabilities in their platforms. The IRA's tactics exploited existing social and political divisions, amplifying contentious issues like race relations, immigration, and gun rights.

6. Key Trump associates had suspicious contacts with Russian officials

"There were contacts between the Kremlin and the Trump team during the campaign."

Pattern of connections. Several Trump campaign officials and advisers had noteworthy interactions with Russian officials or intermediaries:

  • Michael Flynn: Discussed sanctions with Russian ambassador Sergey Kislyak
  • Paul Manafort: Shared polling data with Russian intelligence-linked associate
  • Donald Trump Jr.: Met with Russian lawyer offering dirt on Clinton
  • George Papadopoulos: Told about Russian "dirt" on Clinton by Maltese professor
  • Carter Page: Gave speech in Moscow, met with Russian officials

Investigations and denials. These contacts, initially denied by the Trump team, became the focus of FBI and congressional investigations. While not proving collusion, they raised questions about the campaign's openness to Russian assistance and potential coordination.

The full extent and nature of these interactions remained unclear, fueling speculation and contributing to the ongoing Russia controversy throughout Trump's presidency.

7. The Steele dossier sparked controversy but lacked verification

"I thought I had heard and seen everything in my career. I was horrified."

Explosive allegations. The dossier, compiled by former British intelligence officer Christopher Steele, contained salacious and unverified claims about Trump's ties to Russia, including:

  • Alleged compromising material ("kompromat") held by Russians
  • Supposed coordination between Trump campaign and Russian intelligence

Impact and scrutiny. The dossier:

  • Circulated among journalists and government officials before the election
  • Was briefed to Obama, Trump, and senior intelligence officials
  • Became public when published by BuzzFeed in January 2017
  • Sparked intense debate about its credibility and use in FBI investigation

While some of the dossier's broader claims about Russian interference aligned with U.S. intelligence findings, its most sensational allegations remained unproven. The document's origins and use became a contentious political issue, with Trump supporters claiming it was part of a "deep state" conspiracy.

8. Obama administration grappled with how to address Russian interference

"We were wearing self-imposed handcuffs."

Cautious approach. The Obama administration faced a dilemma in responding to Russian meddling:

  • Concerns about appearing partisan or influencing the election
  • Fear of escalating tensions with Russia
  • Belief that Clinton would win regardless

Key actions and debates:

  • August 2016: Obama warns Putin to "cut it out" at G20 summit
  • October 2016: Public statement attributing hacks to Russia
  • December 2016: Imposes sanctions, expels Russian diplomats

In retrospect, many Obama officials believed they should have taken stronger action earlier. The administration's careful approach, while aimed at preserving election integrity, may have inadvertently allowed Russian interference to continue unchecked.

9. Trump consistently downplayed Russian involvement and praised Putin

"Putin is playing a really tough, long game here."

Pattern of behavior. Throughout the campaign and into his presidency, Trump:

  • Repeatedly expressed admiration for Putin's leadership
  • Cast doubt on U.S. intelligence conclusions about Russian interference
  • Suggested improving relations with Russia was a priority

Examples:

  • July 2016: "Russia, if you're listening, I hope you're able to find the 30,000 emails that are missing."
  • January 2017: Compares U.S. intelligence agencies to Nazi Germany
  • July 2018: Helsinki summit where Trump appears to side with Putin over U.S. intelligence

Trump's stance on Russia became a major point of contention, with critics accusing him of being too deferential to Putin and failing to confront Russian aggression. Supporters argued he was pursuing a pragmatic approach to improve U.S.-Russia relations.

10. U.S. intelligence agencies concluded Putin ordered the influence campaign

"Putin and the Russian Government developed a clear preference for President-elect Trump."

Unanimous assessment. In January 2017, the U.S. intelligence community released a declassified report concluding with "high confidence" that:

  • Putin personally ordered the influence campaign
  • Russia's goals were to undermine faith in U.S. democracy and help elect Trump
  • The operation blended covert intelligence activities with overt efforts

Key findings:

  • Use of state-run propaganda (RT, Sputnik)
  • Cyberattacks on political targets
  • Social media disinformation campaigns
  • Exploitation of WikiLeaks to disseminate stolen information

The intelligence community's conclusions set the stage for ongoing investigations and political battles over Russian interference. While the report did not assess the impact on the election outcome, it highlighted the unprecedented nature and scale of Russia's efforts to influence U.S. politics.

Last updated:

Review Summary

4.21 out of 5
Average of 6k+ ratings from Goodreads and Amazon.

Russian Roulette provides a comprehensive account of Russia's interference in the 2016 U.S. election and Trump's connections to Russia. Reviewers praise the book's detailed chronology and investigative journalism, noting it connects many pieces of the complex story. While some find it lacks new revelations for those following the news closely, many appreciate its organization of known information. Critics argue it presents speculation as fact and shows political bias. Overall, most reviewers consider it an important, well-researched work that illuminates a critical moment in U.S. history.

Your rating:

About the Author

Michael Isikoff is a renowned investigative journalist with a career spanning several major news organizations. He has worked for the Washington Post, Newsweek, and NBC News, earning a reputation for uncovering significant political stories. Isikoff has authored multiple New York Times bestsellers, including books on the Clinton scandal and the Iraq War. His expertise in political investigations has made him a frequent guest on television news programs. Currently serving as the chief investigative correspondent for Yahoo News, Isikoff continues to be a prominent figure in American journalism, known for his in-depth reporting on high-profile political issues.

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