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On Oct. 7, 2016, the Hillary Clinton campaign’s headquarters should have been a sea of smiles. Saturday Night Live even imagined the aides in Brooklyn popping champagne in a skit many in the campaign watched while sipping stale coffee at their desks the following night. The Access Hollywood tape had just been released. Donald Trump’s campaign was in freefall and two top intelligence officials said for the first time Russia was meddling. But the leaks just wouldn’t stop. Starting that day, a dribble of new stolen emails from top Clinton adviser John Podesta sputtered out almost every day until Election Day. The endless revelations made it seem like the campaign couldn’t stay ahead of a fast-moving flow of events beyond its control, likely playing a role in Donald Trump’s surprise victory.
Fast forward eight years and now it’s the campaign of Clinton’s Republican rival—the one who openly encouraged Russia to plunder Democrats’ emails—that is facing similar successful incursions on its servers. This time, according to Trump, it is Iranian players who snuck inside some email accounts and secreted away intel including a 271-page research document about perceived—yet public—vulnerabilities of his running mate, Ohio Sen. J.D. Vance. (The FBI is also tracking attempts to invade President Joe Biden’s campaign that Vice President Kamala Harris has since taken over.)
So far, none of the stolen materials have been published. In fact, some news organizations had been sitting on the goods for weeks before Trump and his team announced on Saturday that it had been hacked and blamed Iran, who also is said to have been plotting an assassination attempt against the former President.
“Any media or news outlet reprinting documents or internal communications are doing the bidding of America’s enemies and doing exactly what they want,” said Steven Cheung, the campaign’s communications director.
It’s no surprise that this week has brought about a fair share of PTSD for anyone who worked through the 2016 hack of Clinton’s emails. Eight years ago, every morsel of that data dump was treated as worthy of picking clean through. This time, though, it seems like there is restraint among newsroom leaders and in voters’ appetite to look at dirty laundry.
While Clinton alumni are publicly condemning the theft, they also still blame journalists, in varying measures, for their candidate’s loss eight years ago. As one aide put it, there was never this level of cautiousness on any story when Clinton was the victim of illegal hacks, let alone one with potentially salacious details.
“This double standard is unconscionable,” one veteran of Clinton’s unsuccessful campaign told me. Added another Clinton veteran who spent 2016 screaming into the void about the unfairness of reading the private messages of Clinton and her inner-circle without permission: “Let’s see if we’ve learned any lessons.”
And yet, there is some level of sympathy for Trump’s predicament from senior Democrats. As one Democrat who was not on Clinton’s payroll but worked with allied outside groups told me: “You all allowed Moscow to become your assignment editors” eight years ago, he said. “Now, it’s over-correction.” Added another with still-fresh frustration: the Clinton campaign “never got the benefit of the doubt.” (Disclosure: I wrote plenty about the emails.)
Still, the collective private reaction among Democrats is a blend of angry and appalled, and not without some degrees of grounding.
The anger is partly at the idea that any campaign would be careless enough in their security to allow this to happen again. There’s also annoyance among Democrats who find themselves forced into an empathetic position toward an adversary who once famously said, “Russia, if you’re listening, I hope you are able to find the 30,000 emails that are missing.”
On a technical level, appalled is also the right lens. Clinton’s email drama came from a hack, but it’s not entirely clear where the Trump ones originated. There is now reporting to suggest there may have been other factors in play for documents that made their way to Politico on July 22 and to The Washington Post on Aug. 8. The Times has not said when it received its files, which reports suggest was identical to what the other two newsrooms received.
So far, there are some major differences between the Russian and Iranian intrusions of importance. For one, Russia in 2016 released their pilfered correspondence publicly, first on a website called DCLeaks, and later through WikiLeaks, making it trickier for the mainstream media to ignore what was revealed in them. At least so far, it seems like Iran is sending specific documents to reporters directly and not just putting everything out for all to see.
The DNC breach was made public in June and July of 2016, and roiled the Democratic Party for months. Thousands of leaked DNC emails came out just before the Democratic National Convention, prompting DNC Chair Debbie Wasserman Schultz and a raft of her team to resign at a moment the party should have been rallying. “We couldn’t be sure, but we feared that more trouble was coming,” Hillary Clinton wrote in her post-campaign confessional. Boy, was she right, as the hackers perfectly timed the release of the Podesta emails to help distract from Trump’s worst scandal yet.
The 2016 leaks were not just a PR nightmare for the Clinton campaign. It also was a huge headache to deal with, sucking up manpower and other resources that had been set aside for rolling out the new running mate, Sen. Tim Kaine of Virginia, and harnessing the enthusiasm after a convention meant for unity and not users’ error with emails. Instead of promoting their candidate heading into a pivotal summer, they were playing clean-up for the DNC and then for their own leaders as leaves turned for autumn.
At the time, Mike Sager was one of the progressive movement’s favorite trouble-shooters and remembers watching as the Democratic Party’s top ranks were pulled into I.T. crises that could have been headed off months earlier. Sager, who later spent six years heading up the tech side of EMILY’s List, a well-connected part of the Democrats’ orbit, still works as a cybersecurity consultant and says no campaign should be treating the integrity of their digital information as an afterthought.
“There are some really basic steps that anyone can take that likely would have prevented this attack from succeeding,” says Sager, who calls “enabling two-factor authentication with a hardware security key” the most important defense. “Keeping a bad actor from getting in the door is easier and more effective than trying to clean up once they’ve trashed the house,” he says.
Along with their frustration with the press, Clinton allies can’t help but point out how Trump in 2016 was incredibly open about his desire for Russia to dig into Clinton’s emails as Secretary of State. Democrats, meanwhile, have been unified and publicly consistent in their opposition to foreign meddling in an election, regardless of beneficiary. Even Robby Mook, Clinton’s campaign manager who later started an anti-hacking nonprofit, has offered to help clean-up Trump’s dodgy IT security in the name of fair elections.
This time around, the potentially damning information—much of it seemingly based on previously available reporting—seems to have hit like a dull thud. As an intellectual matter, it’s precisely what Democrats had hoped would be their fate in 2016. The fact that Trump once again seems to be catching a break—at least thus far—leaves many in Clinton’s orbit frustrated and, not unfairly, a bit stung.
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