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Trump and Clinton's Classified Capers

Both Hillary and Trump had classified information at their homes, but only one may end up legally punished.

(Photo credit should read PAUL J. RICHARDS/AFP via Getty Images)

Let’s compare, Hillary versus Trump and their classified capers. Both Hillary and Trump had classified information at their homes, both appeared to break the law, but only one may end up legally punished. Which one did more damage to national security than the average enemy spy?

In the end, when assessing the damage caused by mishandling classified information, it comes down to exposure: Who saw it? What was seen? And when was it seen?


The "who" part is clear enough. A document left inadvertently on a desktop in an embassy guarded by Marines might be seen by locally hired cleaning staff. A document left on a park bench and seized by the local police risks direct exposure to the host country’s intelligence services, if not sale to the highest bidder.

The "what" is the real stuff of James Bond, and even actual spies. A lot of things are classified, many of which may be overclassified. The director of the National Security Archive at George Washington University estimates 70 percent of the documents he sees are overclassified; Donald Rumsfeld put it at 50 percent. Just because something is marked Top Secret does not mean the information there really is very secret, but it still might rightly be marked Confidential. It would take a knowledgeable person, looking at documents one-by-one, to conclude which seven of the ten were overclassified.

Other times, proper classification is in the eye of the beholder. The secretary of State's daily list of telephone calls to make is always highly classified. It might matter very little to a Russian spy that the secretary is calling the leader of Cyprus on Wednesday but matter an awful lot to the leader of nearby Greece. That is why intelligence services often horse-trade, buying and selling information they pick up along the way about other countries for information they need about theirs. One of the deepest intelligence operations against the State Department involved a European ally who, looking for information on a competitor, listened in on third-party U.S. diplomatic sites where the data was treated like spam.

The "when" aspect is also important, as many documents are correctly classified at one point in their history but lose value over time. One classic example is a convoy notification; it matters a great deal who knows that, tomorrow at midnight, the convoy will set forth from point A to point B. It matters a whole lot less a month later after the whole affair has come and gone and everybody in town saw the convoy arrive.

Finally, we have the unknown factor. Few countries actively harvesting intelligence are in the mood to tell anyone about it. In fact, just the opposite. Spies, even when caught, deny everything, such that one of counter-intelligence's main tasks after catching a bad guy is figuring out what he likely gained access to, and which documents or information he obtained.


Note the "or" there, because it is always information that is classified, not pieces of paper. Much damage can be done with a diplomat's hand-written meeting notes, unmarked by a classification such as Secret, while a document marked Secret might contain nothing worth keeping quiet. The marking on a document is only the drafter's best estimate of what the information on paper is worth. This makes it hard to judge the relative impact of one exposure versus another, but there are ways we can try.

Those are the ground rules. Now onto Hillary versus Trump.

We start the contest with raw number of documents potentially exposed. In Trump's case, we have a decent tally thanks to the Department of Justice. The initial batch of documents retrieved by the National Archives from Trump in January included more than 150 marked as classified. With the recent search raid, more were found. The federal government has recovered over 300 documents with classified markings from the former president since he left office.

This works out to over 700 pages of classified material and “special access program materials,” which is especially clandestine stuff that might include information on the source itself, the gold star of intelligence gathering. If you learn who the spy is inside your own organization, you can shoot him, arrest him, find other spies in his ring, or turn him into a double-agent to feed bogus information back to your adversary. To be clear, our contest is a bit unfair to Trump, as inventories of what was found at Mar-a-Lago are online for all to see.

In Hillary's case, coming to a raw number is very hard, as she destroyed her server before it could be placed into evidence and completely deleted (bleached) many, many emails. Because her stash were email files, the secret files were also not all in their original paper-cover folders boldly marked Top Secret with bright-yellow borders, as in Trump's case. Hillary also stripped the classification markings off many documents as she transferred them from the State Department's classified network to her own homebrew server setup. More on that later.

Nonetheless, according to the FBI, from the group of 30,000 e-mails returned to the State Department, 110 were determined by the owning agency to contain classified information at the time they were sent or received. Eight of those chains contained information Top Secret at the time they were sent, with some labeled as “special access program materials.” Some 36 chains contained Secret information at the time, and eight contained Confidential information. Separate from those, about 2,000 additional e-mails were “up-classified” to make them Confidential. The information in those messages had not been classified at the time they were sent, suggesting they were drafts in progress, in the process of being edited before the ultimate classification assignment.

So, in simple terms based on the meager publicly available information, Trump wins the category for having the most raw material outside an officially secured facility.

In this contest, the "what" is a toss-up. Little information exists on the specific contents of each document trove, though the Washington Post claims one of Trump's documents detailed a foreign country's nuclear capability (ironically, the leak from DOJ that revealed the document's contents suggests things were more secure at Mar-a-Lago than they are now after the search) giving him a slight lead in this category. Clinton only discussed Top Secret CIA drone info and approved drone strikes via Blackberry.

But the real money-maker in the classified world is exposure, and here we finally have a clear leader. For all the noise around Mar-a-Lago, there is nothing to suggest what classified information Trump held was ever exposed; in fact, information available suggests the stuff left the White House to remain boxed up inside a storage room. We know that after classified was ID'd inside Mar-a-Lago by the National Archives, DOJ asked Trump to provide a better lock, which he did, and later to turn over surveillance tapes of the storage room, which he did.

But the clearest evidence of non-exposure is the lack of urgency on the part of all concerned to bust up Trump's classified caper. Claims he removed classified documents from the White House began circulating even as he moved out in January 2021. The first public evidence of classified information in Mar-a-Lago didn't come until January 2022 when the initial documents were seized, and the recent search warrant tailed that by months. If the FBI thought classified material was in imminent danger of being exposed to one of America's adversaries they might have acted with a bit more urgency.

Not so with Hillary. Her server was connected to the internet, meaning that for a moderately clever adversary there was literally only a wire between her computer, with its classified information, and the Kremlin. As the actual Secretary of State Hillary Clinton maintained an unsecured private email server which processed classified material on a daily basis. Her server held at least 110 known messages containing classified information, including e-mail chains classified at the Top Secret/Special Access Program level, the highest level of civilian classification, that included the names of CIA and NSA employees. The FBI found classified intelligence improperly stored and transmitted on Clinton’s server may have been “compromised by unauthorized individuals, to include foreign governments or intelligence services, via cyber intrusion or other means.” How could anyone have gained access to the credentials? Well, Clinton’s digital security certificate was issued by GoDaddy.

We have a winner. Whether anyone unauthorized got a look at Trump's stash remains unclear, but we know for near-certain Hillary's emails were compromised. And by compromised, we mean every email the secretary of State sent, wide open and read—an intelligence officer's dream. Hillary had no full-time physical security on her server, her server was enabled for logging-in via web browser, smartphone, Blackberry, and tablet, and she communicated with it on 19 trips abroad including to Russia and China. It would have taken the Russians almost no time at all to see she was using an unclassified server, and half a tick or two to hack into it. (Hostile actors gained access to the private commercial email accounts of people with whom Secretary Clinton was in regular contact.) Her drafts and documents in progress were extremely valuable to the enemy, giving them, a chance to look over Clinton's shoulder as she made policy.

The actual process Hillary used to move classified material to and from her server from the main State Department and other systems is unknown. If she transferred data the most likely and convenient way, via floppy disk or USB drive, then she likely compromised the State Department systems as well. Her system administrator for the home server was a State Department Civil Service employee she hired, suggesting a link between State computer hardware and the secretary's own. We'll never know, as no search warrant was exercised to seize the server and Hillary's word was taken when she said there was no chance of compromise.

In the end, all we can say about the real winner in this dubious contest is that some intelligence officer in Moscow or Beijing probably got promoted to colonel.


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