Wikileaks, Russian Active Measures, and the 2016 Presidential Election

Peter Grant
18 min readApr 4, 2023

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This article covers the role of the anti-secrecy organization Wikileaks played in the Russian information war targeting the 2016 U.S. presidential election. It is the fourth article in the series “Russian Intelligence, Disinformation, and the 2016 U.S. Presidential Election.” While it is not necessary to read previous entries, it is recommended.

The first article provides definitions for the concepts “Active Measures” and “Disinformation” and provides a history past Russian interference efforts.

The second article provides a description of Russian hacking and cyber warfare efforts in the lead up the the 2016 U.S Presidential Election.

The third article describes how Russia’s Foreign and Military Intelligence agencies breached the Democratic National Committee.

This article is an excerpt from my book, While We Slept: Vladimir Putin, Donald Trump, and the Corruption of American Democracy, available here.

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Higher Impact: Wikileaks, Guccifer 2.0 and the Amplification of the Russian Campaign

On the day the DNC network was brought back online, the infamous Australian hacktivist and founder of the anti-secrecy organization Wikileaks Julian Assange injected himself into events in dramatic fashion. That day Assange gave an interview to the British television station ITV from within his sanctuary in the Ecuadorian Embassy in London, where he had been hiding from Western law enforcement since late 2010.

“We have upcoming leaks in relation to Hillary Clinton, which are great,” Assange claimed, continuing, “Wikileaks has a very big year ahead.”

Assange has described Wikileaks as “an uncensorable system for untraceable mass document leaking and public analysis,” maintained by servers located across the world and hundreds of domain names and friendly mirror sites which make it nearly impossible for its content to be removed from the internet.

In Assange’s view, governments, institutions and political parties that support “authoritarianism” are “conspiracies” that rely upon secrecy, therefore the revelation of these secrets is a direct assault on these so-called conspiracies.

“Consider what would happen,” Assange wrote in a 2006 essay entitled Conspiracy as Governance, “if one of these parties gave up their mobile phones, fax and email correspondence — let alone the computer systems which manage their [subscribers], donors, budgets, polling, call centres and direct mail campaigns. They would immediately fall into an organisational stupor…”

Despite his anarcho-idealist rhetoric, numerous commentators have noted that Assange’s activities through Wikileaks have disproportionately targeted the United States in ways that have often redounded to the benefit of its authoritarian adversaries, in particular Russia.

In November 2010, Wikileaks released a trove of over 800,000 US State Department cables. While many of these cables contained unflattering information regarding Russia, in certain ways the leak proved beneficial to the Kremlin.

For example, under Assange’s direction Wikileaks provided the Russian national Israel Shamir with a large cache of cables that contained unredacted information about political dissidents in the Kremlin-backed dictatorship of Belarus.

Weeks later, Shamir was seen leaving the Belorussian interior ministry and shortly thereafter the country’s authoritarian leader Aleksandr Lukashenko ordered a sweeping crackdown on his political opponents.

The episode was disturbing enough that a number of formerly sympathetic Wikileaks activists were prompted to cut ties with the organization.

In December 2010, Assange was arrested in Britain to face questioning by Swedish law enforcement regarding a rape claim. Assange quickly posted bail and fled to the security of the Ecuadorian Embassy.

Shortly thereafter, Vladimir Putin himself offered words of encouragement to Assange. The day after his arrest, Putin dismissed criticisms of Russia by calling out what he perceived as Western and particularly American hypocrisy. “As far as Democracy goes, it should be a complete democracy. Why then did they put Mr. Assange behind bars?”

Putin continued, “There is an American saying: He who lives in a glass house shouldn’t throw stones.”

In January 2011, Russia issued Assange a visa and one Russian official even suggested that Assange deserved to win the Nobel Prize.

A year later, the Russian state-backed television station RT not only provided Wikileaks with positive coverage, but even gave Assange his own talk show entitled “The World Tomorrow.”

Julian Assange speaking with Hezbollah leader Hassan Nasrallah, on his RT program “The World Tomorrow.”

Assange’s first guest was the leader of Hezbollah, Hassan Nasrallah.

In 2013, Wikileaks played a central role in arranging for NSA-whistleblower and leaker Edward Snowden to receive asylum in Moscow. At Assange’s suggestion, Snowden traveled to the Russian capital accompanied by the Wikileaks activist Sarah Harrison.

Shortly before his bombshell announcement regarding the 2016 American election, Assange offered rhetorical support to Putin. Ironically, he did so by criticizing the Panama Papers, a vast leak of documents that revealed in lurid detail the financial schemes of numerous powerful people around the world, including Vladimir Putin.

Following the release, Wikileaks tweeted that it was a”Putin attack [that] was produced by OCCRP which targets Russia & former USSR and was funded by USAID & Soros.”

The Organized Crime and Corruption Reporting Project, which was instrumental in reporting on the leak alongside the International Consortium of Investigative Journalists and multiple other news outlets, is non-profit funded in part by USAID and the US State Department.

In addition to Assange’s suspicious relationship with Putin’s Russia, his disdain for Hillary Clinton has been well documented.

In November of 2015 Assange wrote to other members of Wikileaks in a Twitter Group Chat that “[w]e believe that it would be much better for GOP to win… Dems+Media+Liberals woudl [sic] then form a block to reign in their worst qualities… With Hillary in charge, GOP will be pushing for her worst qualities., dems+media+neoliberals will be mute… She’s a bright, well connected, sadistic sociopath.”

Shortly after Assange’s promise to release Hillary related leaks, the DNC decided to publicize the fact that they had been the victim of a Russian state hacking operation.

On June 8th, Michael Sussman and several DNC officials met with Washington Post reporter Ellen Nakashima and provided her information on the hack with the understanding that she would withhold publication until the DNC secured its system.

On June 14th, the Washington Post published the article, “Russian government hackers penetrated DNC, stole opposition research on Trump.” CrowdStrike published further technical details of the Russian operation.

The day the Post article went live, a GRU-created Twitter account @dcleaks_ sent Wikileaks a direct message (DM), writing, “You announced your organization was preparing to publish more [sic] Hillary’s emails,” referring to Assange’s cryptic television interview from two days earlier.

They added, “We are ready to support you. We have some sensitive information too, in particular her financial documents. Let’s do it together. What do you think about publishing our info at the same moment?”

Clearly, the GRU had come to the conclusion that DCLeaks.com was failing to arouse adequate attention.

While there is no evidence Assange responded to this initial outreach, Johns Hopkins professor and information security expert Thomas Rid has written that it is likely the GRU passed the contents of John Podesta’s inbox to Wikileaks anonymously sometime prior to June 12th.

That being said, there remains to this day no official account of how Wikileaks came into possession of John Podesta’s emails.

A day after the Post’s bombshell story, officers from Unit 74455 attempted to discredit it by creating an online persona named Guccifer 2.0 and publishing a Wordpress blog that claimed the DNC had been “hacked by a lone hacker.”

Screenshot of the GRU-created Guccifer 2.0 blog

Guccifer was a portmanteau of “Gucci” and “Lucifer” that had previously been used by Marcel Lazăr Lehel, a Romanian hacker who had pled guilty to computer crimes in Federal Court in May, 2016.

That same month, Lehel made the unsubstantiated claim to NBC News that he had gained access to Clinton’s server. Lehel made this claim during a time of feverish, public speculation and a well-known FBI criminal inquiry into Clinton’s use of the server.

The GRU’s Guccifer 2.0 leaked several items that had been stolen from John Podesta’s inbox on its associated WordPress page, including Democratic opposition research into Trump.

Hours before it was published, officers from Unit 74455 had logged into their Moscow based server and searched for a number of specific keywords that were included in the post, including “some hundred sheets,” “illuminati,” and “worldwide known.”

The GRU utilized an old Soviet active measure trick by modifying four out of the five documents by adding a fake watermark across the pages reading “CONFIDENTIAL” to make them seem more important than they actually were. In doing so, however, they made a costly error that assisted online cybersecurity sleuths and subsequent investigators in attributing the leak to Russian Military Intelligence.

The GRU officer who edited to the documents neglected to wipe his metadata left after editing the documents and it was subsequently discovered that the username of the machine behind the edit, written in Russian Cyrillic, was “Feliks Edmundovich,” the nickname for the infamous founder of the Soviet Cheka, Feliks Dzerzhinksy.

Founder of the Cheka, the USSR’s first secret police and intelligence services, Feliks Dzerzhinksy

Before ending the post with, “Fuck the Illuminati and their conspiracies!!!!!!!!! Fuck CrowdStrike!!!!!!!!!,” Guccifer 2.0 claimed to have sent “thousands of files and mails” to Wikileaks.

In reality, the GRU had yet to transfer its stolen files to Wikileaks. The GRU may have been using the Guccifer 2.0 persona to signal its intentions to Julian Assange that they wanted to send him files for Wikileaks to publish.

Wikileaks acknowledged Guccifer 2.0’s post, writing in a June 15th tweet, “DNC ‘hacker’ released 200+ page internal report on Trump, says gave Wikileaks the all [sic] rest.”

“Do you have secure communications?” Wikileaks wrote to Guccifer 2.0 a week later via Twitter DM. “Send any new material here for us to review and it will have a much higher impact than what you are doing. No other media will release the full material.”

Between June 15th and October 16th, 2016, the GRU released thousands of DNC and DCCC documents through their Guccifer 2.0 Wordpress.

In addition to releasing stolen documents and emails online, the GRU used Guccifer 2.0 to reach out to journalists and political operatives and candidates in the United States.

On June 27th, 2016, Guccifer 2.0 reached out to the American news outlet The Smoking Gun operated by the Reporter William Bastone in an email with the subject line “leaked emails” in which they offered to provide “exclusive access to some leaked emails linked [to] Hillary Clinton’s staff.”

The GRU ultimately sent Bastone a password that granted him access to a portion of documents on the DCLeaks.com website.

On July 6th, Wikileaks reached out to Guccifer 2.0 via Twitter yet again.

“[I]f you have anything hillary related we want it in the next tweo [sic] days prefable [sic] because the DNC is approaching,” Wikileaks wrote, referring to the upcoming Democratic National Convention. “She will solidify bernie supporters behind her after.”

“ok . . . i see,” Guccifer 2.0 replied.

Wikileaks went on to explain to the Russian intelligence officers, who apparently weren’t as savvy regarding American domestic politics, that the Democratic Party was experiencing internal divisions.

“we think trump has only a 25% chance of winning against hillary,” Wikileaks wrote, “so conflict between bernie and hillary is interesting.”

After several failed attempts to transfer the the files over to Wikileaks in late June, on July 14th Guccifer 2.0 sent Wikileaks an email with the subject line “big archive” an encrypted attachment titled “wk dnc link1.txt.gpg” that contained detailed instructions on how to access a hidden online archive of stolen DNC emails.

Four days later, Wikileaks replied that it had gained access to “the 1gb or so archive” of documents and promised to publish them “this week.”

On July 22nd, three days before Hillary Clinton was set to receive the Democratic nomination in Philadelphia, Wikileaks released over 20,000 stolen DNC emails. The GRU’s clandestine cyber espionage campaign had now officially morphed into political warfare through active measures.

Nor were these active measures limited to the release of stolen emails, but also of weaponized disinformation.

On July 10th, four days after Wikileaks first reached out to Guccifer 2.0 requesting the leaked files, 27-year old DNC staffer Seth Rich was shot in the back while walking through the Bloomingdale neighborhood in Washington, DC and died an hour and a half later. While the reasons for his murder remain unknown, local police believed Rich’s death was due to a botched robbery.

Murdered DNC staffer Seth Rich

Three days later, the Russian foreign intelligence agency the SVR released a forged intelligence “bulletin” claiming that Rich was on his way to the FBI to provide information on Hillary Clinton and had been assassinated by a Clinton hit squad.

Russian television stations, online trolls, Julian Assange himself and the right wing media ecosystem in the United States would run with the false story throughout the rest of the election and for years to come after that.

Aftershocks: The Clinton and Trump Campaigns React to the Leaks

The Wikileaks dump came at a fraught moment for the Clinton Campaign. After defeating Bernie Sanders in a much tighter race than anyone expected, the Clinton Campaign wanted to use the Democratic National Convention to bring the party together and rally it behind her candidacy. However, the contents to the DNC emails would make that significantly more difficult.

Furthermore, the leaks came on the heels of yet another email controversy. Just a few weeks earlier, on July 2rd, Clinton spent three and a half hours answering questions posed by two FBI agents at the J. Edgar Hoover building in Washington, DC. It was the final interview to close out the FBI’s criminal investigation into Clinton’s handling of classified information in her emails during her tenure as Secretary of State.

While the FBI found that Clinton was not guilty of any criminal wrongdoing, it’s Director James Comey feared that the public would view their findings as being politically motivated. As a result, he took the extraordinary step of calling a press conference on July 5th without informing the leadership at the Obama Justice Department.

FBI Director James Comey with President Barack Obama

During the press conference, Comey also violated the FBI’s long standing tradition of not casting judgment on individuals they do not charge with a crime.

“They do not know what I am about to say,” Comey said, opening the press conference by emphasizing that he had not coordinated his remarks with the Attorney General Loretta Lynch or anyone else at the Obama Justice Department. “Although we did not find clear evidence that Secretary Clinton or her colleagues intended to violate laws governing the handling of classified information, there is evidence that they were extremely careless in their handling of very sensitive, highly classified information.”

While the FBI didn’t press any criminal charges against Clinton, Comey’s “extremely careless” remark did little to dispel the aura of scandal around Hillary’s emails.

Later analysis by the Columbia Journalism Review revealed that the American media dedicated more coverage to the Clinton email scandal than all of Trump’s voluminous campaign scandals combined.

While Clinton’s first instinct was to hit back hard against Comey’s “extremely careless” characterization, her staffers cautioned her against a confrontational approach and suggested they just move on from a scandal that, they incorrectly assumed, had finally been put to bed.

What the Congressional Republicans in the various Benghazi investigations and now the Director of FBI had succeeded in doing was to turn the term “Clinton emails” into shorthand for “Clinton corruption.”

Thus, when Wikileaks leaked the DNC’s hacked internal communications, the event was filtered through a pre-existing media narrative that associated Clinton-related emails with a criminal investigation and was presented to an American public that was already primed to associate Clinton’s emails with corruption.

Little to no attention was paid to who stole the emails in the first place and what the purpose of the leak itself was.

The leaked emails included ones in which the chairwomen of the DNC, Debbie Wasserman Schultz, who was meant to be a neutral arbiter in the nominating process, referred to Bernie Sanders’ campaign manager Jeff Weaver as a “[d]amn liar” and “an ass.”

In another, Schultz wrote to a DNC colleague regarding Sanders, “[h]e isn’t going to be President.”

Other examples of anti-Sanders sentiment included calls to question his faith and descriptions of his campaign as “a mess.”

While private snark and preferentialism are nothing new to political parties, many Sanders supporters who already believed they had been treated unfairly by the DNC erupted in indignation.

In the ensuing storm, Schultz was forced to step down from her position the day before the convention.

While the Clinton and Sanders Campaigns had been working together since June to smooth over their differences, there was still lingering bitterness in the Bernie camp about his treatment in the primary and frustration among Clinton supporters that Sanders seemed unable to get his followers in line.

When the convention finally rolled around, disgruntled Sanders supporters protested outside the venue and on a few occasions scuffled with Philadelphia law enforcement. In one instance an American flag was burned.

Bernie protestors and the 2016 Democratic National Convention (courtesy of The New York Times)

When Clinton was officially nominated, a contingent of hardcore Sanders supporters walked out of the convention hall chanting, “This is what democracy looks like.”

While Sanders himself urged his supporters to support Clinton, Julian Assange’s prediction to the GRU that the leak would exacerbate inherent tensions within the Democratic party proved prescient.

Clinton campaign manager Robby Mook attempted to explain to the press that the leaks were due to Russian hacking and were an attempt to aid Donald Trump, but the story gained little traction.

“Listen, does it even matter who hacked this data?” Vladimir Putin glibly asked in reference to the DNC leaks while being interviewed in Vladivostok.

“The important thing is the content that was given to the public.” Putin continued, “There’s no need to distract the public’s attention from the essence of the problem by raising some minor issues related with the search for who did it.”

When pressed further about Russia’s involvement, Putin replied, “I want to tell you again, I don’t know anything about it, and on a state level Russia has never done this.”

According to deputy campaign manager Rick Gates, the Trump campaign was “very happy about the release.”

While they may have been happy, they were not surprised.

Sometime beginning in April or May of 2016, the infamous political consultant Roger Stone, now a convicted felon, informed Donald Trump personally and a number of high level members of his campaign that Wikileaks was preparing to release information that would be damaging to the Clinton campaign.

Donald Trump’s longtime friend and political advisor Roger Stone

Read my in-depth article about Roger Stone’s interactions with Russian military intelligence and Wikileaks here.

While Stone had been fired from his position on the campaign in August of 2015 (he maintains he left on his own accord), Stone remained closely connected with the campaign in an unofficial capacity.

Prior to the DNC dump, Trump campaign officials held regular “family meetings” with members of the Trump family and Donald Trump Jr. would regularly inquire about the location of the 30,000 emails “missing” from Clinton’s private server.

Other campaign associates interested in locating the emails included prominent Trump surrogate and former head of the Defense Intelligence Agency Michael Flynn, Trump’s Son-in-Law Jared Kushner, Trump’s first campaign chairman Corey Lewandowski and his replacement Paul Manafort, Alabama Senator and Trump supporter Jeff Sessions and Trump campaign policy advisor Sam Clovis.

At some point in this timeframe, Stone told Rick Gates that the Clinton-related documents provided to Wikileaks could have come from the Russians.

When on June 12th Julian Assange made a public announcement that Wikileaks was preparing to release leaks related to Hillary Clinton, Gates later testified that the campaign was elated and considered the leaks a “gift.” At the time of the announcement, the Trump campaign believed that Wikileaks possessed emails from Clinton’s personal server.

Paul Manafort told Gates that the Republican National Committee was “energized” by the potential of Clinton-related Wikileaks dumps and that the RNC was going to “run the Wikileaks issue to ground.”

Trump and Kushner were both willing to cooperate with the RNC on a Wikileaks strategy.

When The Washington Post reported on June 14th that the DNC had been hacked by the Russians the Trump campaign reacted positively to the news. According to Gates, the responses among those in the campaign ranged from disbelief to feeling that it would benefit the campaign if the information were eventually released.

At this point, the Trump campaign began planning “a press strategy, a communications strategy, and messaging based on the possibility the emails existed.” Further conversations were held among Trump campaign staffers “about what the campaign could plan for in the way of emails.”

A day after the Post story, Paul Ryan and Republican House Majority Leader Kevin McCarthy (a future Republican House Majority Leader) attended a meeting with the Ukrainian Prime Minister Vladimir Groysman in which Groysman described how the Kremlin funds right-wing, populist candidates across Europe to destabilize democracy in the region.

Donald Trump and Republican Congressman Kevin McCarthy

“I’ll guarantee you that’s what it is,” Kevin told Ryan and several other Republican Congressmen after the meeting. “The Russians hacked the DNC and got the opp [opposition] research they had on Trump.”

McCarthy continued, “There’s two people I think Putin pays: Rohrabacher and Trump.”

Several of the gathered lawmakers, not knowing that the interaction was being recorded, laughed at McCarthy’s reference to his colleague in the House Dana Rohrabacher and the presumptive Republican nominee for President.

“Swear to God,” McCarthy added.

Ryan quickly interjected. “This is an off the record. No leaks, alright? This is how we know we’re a real family here.”

A few minutes after Midnight on June 16th, hours after the emergence of the GRU-created online persona Guccifer 2.0 and the first release of hacked documents on its Wordpress site, Stone and Gates spoke over the phone about the DNC hack.

Stone again told Gates that “more information would be coming out of the DNC hack.”

Stone then asked Gates to send him Jared Kushner’s contact information as he wanted to brief him on the Wikileaks documents. While Gates sent Stone Kushner’s info, it is not known if Stone contacted Kushner.

Roger Stone held multiple private conversations with Trump in which they discussed Wikileaks and the Clinton emails in the months and weeks prior to their July 22nd DNC leak.

Stone called and was called by phone numbers related to the Trump Organization on multiple occasions throughout the latter half a June and the Senate Intelligence Committee assessed that Stone connected with Trump and discussed the upcoming Wikileaks disclosures.

On either July 18th or 19th, Trump’s private attorney Michael Cohen recalled sitting in Trump’s office when he overheard Trump’s assistant Rhona Graff call out, “Mr. Trump, Roger Stone on line 1.”

“Roger, how are you?” Trump asked his old friend, speaking over speakerphone.

“Good,” Stone replied according to Cohen. “I just want to let you know I got off the phone a moment ago with Julian Assange. And in a couple of days, there’s going to be a massive dump of emails that’s going to be extremely damaging to the Clinton campaign.”

“Uh, that’s good, keep me posted.” Trump hung up the phone and turned to Cohen. “Do you believe him? Do you think Roger really spoke to Assange?”

“I don’t know,” Cohn said. “Roger is Roger, and for all you know, he was looking at his Twitter account. I don’t know the answer.”

Within days, on July 22nd, Wikileaks dropped the DNC emails.

“I guess Roger was right,” Trump said to Cohen.

Later that day Trump and Manafort, both excited by the release, discussed how they could use the leaked emails against Debbie Wasserman Shultz.

Trump tweeted shortly after the release, “The Wikileaks e-mail release today was so bad to Sanders that it will make it impossible for him to support her, unless he is a fraud!”

In addition to including references to the leaked emails into his talking points, Trump also used them to attempt to exacerbate the divisions between the Clinton and Sanders wings of the party, exactly as Julian Assange had predicted to the GRU in their Twitter conversations earlier that month.

Trump not only took advantage of the stolen communications hacked by the GRU and disseminated by Wikileaks, he dismissed the idea of any Russian involvement.

In a July 25th tweet Trump wrote, “The new joke in town is that Russia leaked the disastrous D.N.C. emails, which should never have been written (stupid), because Putin likes me.”

Then, after rejecting the idea that Russia was involved in the leak, Trump encouraged them to become involved.

At a news conference on July 27th, in perhaps the most infamous moment of the entire campaign, Trump said before the entire world, “Russia, if you’re listening, I hope you are able to find the 30,000 emails that are missing. I think you will probably be rewarded mightily by our press.”

Within five hours of Trump’s remarks, the GRU targeted Clinton’s personal office. Lieutenant Lukashev of Unit 26165 sent spearphishing emails to 15 email accounts at a domain hosted by a third party server and used by Clinton’s personal office. He then targeted seventy-six email addresses at a domain for the Clinton campaign.

Apparently, when Trump spoke the GRU was listening.

The next article in the series will examine how the U.S. intelligence community and the Obama Administration responded to the Russian interference campaign.

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