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How This CEO Got Caught Up In the Clinton Email Scandal

Datto chief Austin McChord never dreamed he’d get caught up in one of the most consequential political dramas ever.

How This CEO Got Caught Up In the Clinton Email Scandal
[Photo: Flickr user Bill B]

Months after the election, we still don’t know for sure what happened to all of Hillary Clinton’s emails, the ones that passed through her private email server, a question that remains unresolved and continues to infuriate some of President-elect Donald Trump’s die-hard supporters. But one clue to unraveling the mystery may lie with a low-key tech company based in southwestern Connecticut and its 31-year-old freckle-faced CEO, who handed over up to 17,448 deleted Clinton emails to the FBI.

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Datto, a data protection company, had been backing up Clinton’s messages for years, yet nobody seemed to know about it—not the techie who tended to the Clintons’ private email server, not the Clintons, not even Datto’s CEO Austin McChord and his employees. When the company’s role was first revealed last spring, Datto was thrust into the spotlight, and McChord’s face ended up at the top of Drudge Report. The drama caught the redheaded technology entrepreneur by surprise. The man who nine years ago had started his now billion-dollar company in a basement, building his first product partly out of Legos and hot glue, was even forced to buy a suit when it looked like he might have to testify on Capitol Hill.

McChord and Datto found themselves cast in bit roles in the mystery to end all political mysteries: What happened to Hillary Clinton’s deleted emails? You know, the some 30,000-odd thousand missing messages—out of more than 60,000—she sent and received while serving as secretary of state, using not the government’s system but her own private email server. Clinton has maintained all along that they were nothing more than personal correspondence, dealing with plans for daughter Chelsea’s wedding, family vacations, and yoga routines.

Austin McChord

But FBI investigators found several chains of work-related emails, some classified, that weren’t included in those turned over by her lawyers. In total, the bureau has “recovered from additional data sources” 17,448 of Clinton’s emails, according to an FBI report released last summer. Some of those emails may have come from Gmail accounts of Clinton associates that were hacked (the Obama administration blames the Russians) and later published by WikiLeaks. Others presumably came from Datto–the FBI report only lists three sources of the emails it recovered: Clinton, WikiLeaks, and Datto.

In any case, the revelation that Clinton had been using a private email server for her missives prompted Clinton’s right-wing critics to assume a conspiracy afoot: Clinton must have deleted these personal email messages because she had something to hide. Eleven days before the election, FBI director James Comey rocked the presidential campaign by announcing that the bureau was reviewing a new cache of emails that agents discovered on a machine shared by Clinton aide Huma Abedin and her husband, disgraced former congressman Anthony Weiner. In the days after Comey’s announcement, public opinion shifted toward Trump by four percentage points, according to polls. When those emails didn’t turn up any red flags, a fact the FBI director revealed just two days before the election, it was probably too late to blunt any impact it may have had on her candidacy. It’s difficult to determine the true extent of Comey’s actions, but Clinton blames the FBI director for costing her the presidency.

There are plenty of theories about what happened to the deleted emails. William Binney, who architected the National Security Agency’s surveillance program and later became a whistleblower, claims his old agency must have them. Former U.N. ambassador John Bolton thinks the Russians got them. U.S. Representative Trey Gowdy (R-S.C.), who helmed the House Benghazi committee, is less sanguine, saying he believes they are “where even God can’t read them.”

Far From The Madding Crowd

Unlike many Silicon Valley entrepreneurs who have built successful technology companies, Austin McChord operates far outside the limelight. He cares little for fame and considers himself a geek’s geek. Few know who he is outside of tech conferences, where he’s hounded for his autograph. Instead of hobnobbing with the tech cognoscenti, he spends his spare time building and racing drones, which he joyously crashes to the ground . . . just because.

McChord’s Norwalk, Connecticut, data protection company, Datto, Inc., isn’t sexy, and until recently most of the media coverage it received was from the trade press. That’s because Datto isn’t like Apple; it doesn’t sell must-have consumer products that change how we interact with the world. Unlike Twitter, it doesn’t provide a platform for journalists, celebrities, trolls, and 300 million other people, or bring together more than a billion people around the planet like Facebook. Datto is more like an insurance policy (without the wry gecko mascot or clever TV commercials).

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Datto provides what it calls a “hybrid cloud solution.” This involves a small box that sits atop a server and takes a complete snapshot of everything on it every 15 minutes, half hour, hour, or day, depending on how it is set. That snapshot, which includes all operating systems, applications, emails, and any other content, is encrypted and transmitted to Datto’s servers that are housed in Pennsylvania.

In essence, Datto acts as a time machine. It’s a hedge against the unexpected. A customer who has been hacked or suffered an outage can travel back to a point just before trouble started. The server can be rebooted and the data retrieved on demand in as little as six seconds.

Nine years ago, McChord started the company in the basement of his father’s office. Then 22, he was taking time off from the Rochester Institute of Technology, where he studied bioinformatics. One day he set his mind to cobbling together a backup and data recovery device with a smattering of Linksys parts, a few Lego pieces, and gobs of hot glue in his dad’s office basement. His tool of choice: a soldering iron. His company’s first product, the Datto 100, was born.

Today Datto is one of those big companies you’ve never heard of, operating in the background much like its technology does. More than 50,000 mostly small and mid-sized businesses rely on Datto, which handles more than 250 petabytes of data, performs a million backups a day, and protects hundreds of thousands of physical and virtual servers globally.

Datto’s hellacious growth owes much to the rampant increase in ransomware, a kind of malicious software that blocks access to a computer network by encrypting files until the victim pays a ransom. Kaspersky Security Networks call such attacks a “pandemic.” Symantec estimates that throughout 2015, ransomware infections fluctuated between 23,000 and 35,000 per month, impacting one out of every two organizations.

Digital thugs hailing from Russia, India, and Kazakhstan, where many ransomware fraudsters live, don’t intimidate McChord. But FBI agents, congressional committees, and journalists like me all demanding answers are a different matter. After meeting with me once, McChord would only agree to answer my questions about the Clinton server through his company lawyer and chief marketing officer.

BlackBerry Addict

After Hillary Clinton was appointed secretary of state in early 2009, she insisted on using her BlackBerry to stay in close contact with a small group of trusted staffers who fielded inquiries to her without going through the hassle of finding safe, secure modes of communication. When Condoleezza Rice served as secretary of state during the Bush Administration, she had managed to wrangle a few secure BlackBerrys for herself and some aides. Clinton requested a similar arrangement—pointing out that President Obama had a secure BlackBerry for personal use. Each time the State Department’s assistant director for security infrastructure, Donald R. Reid, asked for such a device for Clinton, the NSA, citing security concerns, turned them down. (For his part, President-elect Donald Trump is reportedly worried he won’t be allowed to use his beloved Android phone after he moves into the White House.)

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Clinton reportedly has never used a personal computer and was leery of email in any case because she worried about leaving a paper trail after years of being the target of what she deemed a “vast right-wing conspiracy.” At a private fundraiser in 2000, she was caught on a private video telling a donor, “As much as I’ve been investigated . . . Why would I ever want to do email? Can you imagine?”

Donald Trump isn’t tech-savvy, either. As recently as 2013, Trump, a compulsive tweeter, admitted he used email “rarely,” and when he did, often dictated messages to an assistant. In the second presidential debate, he threatened, if elected, to send Hillary Clinton to prison for the “emails that you deleted and that you acid washed,” calling it “an expensive process” (it’s not). He was referring, of course, to the 31,830 personal emails that her lawyers had expunged from her home-brew server with the aid of a free, open-source software called BleachBit—although Trump made it sound like they had relied on a chemical process for stone-washing jeans in the 1980s.

Given Clinton’s tech ignorance and paranoia about protecting her privacy, it’s easier to understand why Clinton could have made such a colossal error in judgment in allowing State Department email accounts to be set up on the Clinton family server in her basement in Chappaqua, New York.

11 BlackBerrys, 5 iPads, And A Few Clunky Servers

At the start of her tenure at the State Department, Clinton, along with several of her aides, started using a personal clintonemail.com account hosted on a server in her basement in Chappaqua that already handled email for the Clinton Foundation. The antiquated server was plagued by service outages and delays and was later upgraded to a Dell PowerEdge 2900, which is what served email for the entire four years Clinton served as secretary of state.

Maintenance and upkeep had been haphazard. At one point, an external Seagate hard drive was connected to the server, conducting daily backups, with a full backup performed weekly. Given the volume of email, the Seagate was a poor choice. As it filled up, the oldest backups were deleted on a first-in, first-out basis to make room for new messages. Thousands of email from her early years at the State Department tenure were erased, although they remained on the Clinton home server. Eventually the overtaxed Seagate device was upgraded to a more appropriate storage system, a Cisco Network Attached Storage (NAS) device. It’s not clear how frequently the NAS captured backups of the server.

Clinton’s attachment to her BlackBerry only compounded the problems. While serving as secretary of state, Clinton would stash her BlackBerry in a desk drawer at a guard station located outside her seventh-floor office, which is considered a secure location. For convenience’s sake, she refused to carry two separate devices, nor would she use a secure computer, and mingled her official State Department email with her personal account. Like a smoker forced to leave the building to light up a cigarette, throughout the day Clinton would grab her BlackBerry and go to the State Department’s eighth-floor balcony. When she was on the road or at home in Chappaqua, she also read and replied to email on an unsecured iPad.

Clinton went through 11 BlackBerrys and five iPads in four years. Some of her Blackberrys were destroyed by a staff member (he used a hammer to smash them to bits, which is standard operating procedure). Others were given away to staff. Still more remain unaccounted for. The 62,320 emails Clinton sent and received from hdr22@clintonemail.com may sound like a lot, but it works out to an average of 296 emails a week, or about 1,300 a month.

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To put it in perspective, consider the George W. Bush administration’s email scandal, one that dwarfs Clinton’s. Between 2003 and 2009, the Bush administration “lost” 22 million emails written during a tumultuous time that included the Iraq War and the scandal over the politically motivated firings of federal prosecutors. The private server handling the White House email was owned and operated by the Republican National Committee. Not only did the White House not retain these emails as required by law, it refused to comply with a congressional subpoena. Imagine if Hillary Clinton and the Democratic National Committee had done that.

For her part, Clinton later told the FBI she did not recall receiving any emails she thought shouldn’t be on an unclassified system. According to the report, “She relied on State officials to use their judgment when emailing her, and could not recall anyone raising concerns with her regarding the sensitivity of the information she received at her email address.”

The FBI report notes several attempts to hack the Clinton server, although none were successful, as far as the agency could determine. The same cannot be said of the State Department’s email system, which ran on antiquated Wang machines well into the 2000s until Colin Powell ordered an upgrade. Since then, it has been hacked repeatedly. In November 2014, the State Department took its email system offline over the course of a weekend in a bid to improve security. The following year, a federal law enforcement official called a series of Russian-linked cyberattacks on State Department computer systems over the course of 2015 as the “worst ever.”

The only times that Hillary Clinton’s State Department emails have been made public has been through Wikileaks, which has shared a large number of emails stolen from the accounts of longtime Clinton associates John Podesta and Sidney Blumenthal. That is astounding, given how insecure and haphazard Clinton’s computer security was.

Think about it: Hillary Clinton’s lightly attended, home-based email server turned out to be more secure than the State Department’s ostensibly well-fortified computer network.

Where Are The Deleted Emails?

A Datto reseller, Denver, Colorado-based Platte River Networks, a small company with no official government security clearances, took over administering the Clinton server in June 2013, moving it to Secaucus, New Jersey. The Platte technician intended to use Datto to provide backups in case the server failed. Though the company took Clinton’s old Cisco server and migrated the contents to their own machines, it’s not clear how much data was recovered and how far back it went, according to an FBI report.

This was several months after Hillary Clinton left the State Department, but that didn’t matter to the Datto box. Its purpose was to capture everything on the server from the moment the box was switched on. Platte River technician Paul Combetta set up the server to automatically delete email every 60 days, as he had been told to, and installed the Datto device to provide localized backups in case the server suddenly went down or hackers managed to take root. The Datto box was also configured to delete anything older than 60 days. What he didn’t realize was the local Datto device was beaming a complete snapshot of the Clinton server multiple times a day to Datto’s cloud servers–and those backups were not being deleted every 60 days. In fact, they weren’t being deleted at all.

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When Hillary Clinton’s lawyers turned over 33,000 work-related emails to investigators, Clinton aide Cheryl Mills ordered Combetta to delete all emails on the server that weren’t work-related. Five months later, on March 3, 2015, the day after the New York Times reported that Clinton had used a personal server while serving as secretary of state, the House Republicans’ Benghazi committee ordered all emails on the private server to be preserved. Combetta told FBI investigators that he had what he called an “oh, shit” moment when he realized he hadn’t actually deleted those 31,830 personal emails.

After a conference call involving Mills, Clinton’s legal representatives, and Platte River Networks staff, Combetta used BleachBit to delete the emails, despite later admitting to investigators that he “was aware of the existence of the preservation request and the fact that it meant he should not disturb Clinton’s email data on the PRN server.” Combetta claimed he received no guidance from anyone on the meaning of the preservation request. Both Mills and Clinton stated they were unaware that the emails had been deleted after the Committee on Benghazi requested they be preserved.

It wasn’t until August 2015, more than two years after Platte River had taken over administering the Clinton server and four months after Combetta deleted the emails off the server, that anyone realized that cloud-based backups existed. In an email dated August 6, Sam Hickler, Platte River’s VP of operations, wrote: “When we made the purchase, it was under the understanding that we didn’t want to back up to Datto’s data center.”

Datto investigated and discovered that the device Combetta had installed was automatically syncing with Datto’s cloud servers and storing the data there—even though Platte River hadn’t been billed for the service.

Treve Suazo, Platte River’s CEO, replied: “This is a problem. This data should not be stored in the Datto Cloud, but because the backup data exists, we cannot delete it . . . ”

A few days later, Datto’s general counsel, Michael Fass, sent a letter to Platte River attorneys, informing them that Datto planned to disconnect the cloud-based server. Fass said that Datto had been following news reports concerning various investigations into Clinton’s emails and had concerns. “It may be possible that information contained on the Datto device” is “subject to legal retention requirements,” he said. “We are concerned that if no immediate action is taken,” then “information may be improperly deleted.”

The following month Datto received its first written request from the FBI (there was no subpoena).

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“We received permission from both Platte River and the Clinton organization to hand over to the FBI information relevant to its investigation including physical equipment from our cloud, which we did,” Datto CEO Austin McChord told me through his attorney.

Datto provided the physical cloud storage equipment as well as individual syslog files and additional logs to the FBI.

The question is: Did Datto maintain the integrity of these cloud-based backups of Clinton’s emails after Platte River asked it to discontinue secure cloud backups?

All McChord would say after consulting his attorney was: “The FBI Report provides that Platte River Networks used Datto to back up the Clinton IT infrastructure. It also states that Platte River Networks used our solution to back up servers that had Mrs. Clinton’s emails on them. The report also indicates that the FBI was able to recover emails that were not previously provided.”

Is that a yes?

“Datto has no direct knowledge to suggest those emails were recovered from the Datto servers.”

How about indirect knowledge?

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Datto pointed me back to the FBI report, which stated that the bureau recovered “from additional data sources” 17,448 emails that were sent to and from Clinton’s hdr22@clintonemail.com and were not previously provided to the agency. Some might have come from Wikileaks’ hacked email from Podesta’s and Blumenthal’s Gmail accounts. The vast majority, however, might have come from Datto’s backups.

After handing over Datto’s servers and logs that held the Clintons’ emails, McChord says Datto hasn’t heard anything more from the FBI and has no indication that the Bureau had trouble decrypting those files.

But what was in them? Datto isn’t entirely sure. Nonetheless, it’s the missing emails that Clinton sent at the time of the Benghazi attacks that led to the investigation in the first place. The attack occurred during the final months of Clinton’s tenure at the State Department. Recall that the Seagate external hard drive that a techie installed on the Clinton server in 2009 deleted the oldest messages first as it filled up. These more recent Benghazi-era messages could have been stored and transferred to a newer server, taking the place of the older, antiquated one, if we have connected all the dots properly. Of course, we don’t know for sure that they were still on the server when Datto handed over its data to the FBI. Comey has never clarified this (and neither the FBI nor the Clinton campaign responded to my requests for comment).

As long as the whereabouts of these emails remain a mystery, this story is not going to die. Some of them really might be gone forever; some might be somewhere no one has even thought to look. The whole mess is a stark reminder that our most private data could be in places we least suspect. Even when we think we’ve deleted them, these zombie emails can linger on servers run by companies we’ve never even heard of before.

Meanwhile, McChord is still in Norwalk, running his company, smashing homemade drones, and like many Americans, trying to put the drama of this tumultuous presidential campaign behind him. And he’s relieved he never had to wear that new suit to a hearing in Congress.

About the author

Adam L. Penenberg is a journalism professor at New York University and author of several books.

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