Hillary Clinton versus Donald Trump versus Joe Biden. All three kept classified information at their homes. Who wins—that is to say, who is most likely to have done grave damage to national security?

In the end, when dealing with the damage done by mishandling classified information, the fundamental question is one of exposure: Who saw it, what was it, when was it seen, and for how long?

The “who” part is clear enough; a document left inadvertently on a desktop in an embassy guarded by Marines might not be seen by anyone, while 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. But never underestimate cleaning staff; spies love ’em. In what other capacity are locals allowed to rummage through an embassy at night, picking through the trash, and moving things around on desks to um, dust?

The “what” and how much of it is the real stuff of James Bond. At times “what” 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 an awful lot to the leader of nearby Greece. That is why intelligence services often horsetrade, buying and selling info they pick up along the way about other countries for info they need about theirs.

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 lot who knows tomorrow at midnight the convoy will set forth. It matters a whole lot less a month later after everybody in town saw the convoy arrive. “How long” can matter as well, as the longer a document is exposed, the more chances someone unauthorized has to see it.

“Who” between Trump and Biden seems a toss-up, given that as far as we know both kept classified information in locked closets (we’ll turn to Clinton and her server below.) An investigator would want to know who had keys to that lock, and if possible, who used them when. What controls if any were in place to prevent duplicates from being made? What kind of lock was used? Was it pickable? Would cleaning staff or painters have had time alone to work the lock? Were there any video or access logs that might show the staff spent an inordinate amount of time near the closets? We know nothing about this regarding Trump’s and Biden’s closets.

One might also want to get into who packed the boxes containing classified info, on whose orders, and how much exposure did they get en route to those naughty closets. Did the information sit in an unguarded truck stop overnight in 2010? Who would have known? “Who” is more than a name; it is a line of dominoes.

We have a start on the “what” that may have been compromised, and it is not good. Clinton, Trump, and Biden mishandled information at at least the SCI level (Sensitive Compartmentalized Information, above Top Secret.) SCI means that not only is the document classified, but that even seeing it is restricted to a specific list of people such that merely holding a full Top Secret clearance is not enough. We can say the documents included some real secrets as of their drafting.

Next of concern is the 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 classified. With the raid, the government recovered over 300 classified documents from Trump. This worked out to over 700 pages of classified material and “special access program materials,” especially clandestine stuff that might include info 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.

Our contest is a bit unfair to Trump, as inventories of what was found at Mar-a-Lago are online for all to see while the pro-Biden media has been very cagey on how many documents have been found, using phrases like “several” and “a few dozen.” We’ll have to wait until Biden’s home is raided or the special counsel concludes his investigation to know for sure.

In Clinton’s case, just coming to a raw number is very hard, as she destroyed her server before it could be placed into evidence. Because her stash was email, 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. Clinton also stripped the classification markings off many documents in the process of transferring them from the State Department’s classified network to her own homebrew server setup.

Nonetheless, according to the FBI, from the group of 30,000 emails returned to the State Department, 110 contained 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, around 2,000 additional emails were “up-classified” to make them Confidential; the information in those had not been classified at the time the messages were sent, suggesting they were drafts in progress, in the process of being edited before a classification was ultimately assigned.

The “what” is a toss-up for now. Little information exists on specifically what each document trove held, though The Washington Post claims one of Trump's docs detailed a foreign country’s nuclear capability (ironically, the leak from DOJ revealing the document’s contents suggests things were more secure at Mar-a-Lago than after the search) giving him a slight lead in this category. Clinton discussed Top Secret CIA drone info and approved drone strikes via Blackberry.

As for the “when” category, Biden’s classified materials date back to his Vice Presidency. We don't know when they were moved out of secure storage, so the material possibly dates back as far as 2009. That’s potentially 14 years of paper hanging around waiting for someone to make nefarious use of it. In Trump's case, he left the White House in January 2021 and the classified material was pulled out of Mar-a-Lago no later than August 2022, only some 20 months of hiding for no more than four years of material.

Investigations are ongoing in both cases, but there is no evidence to date that anyone unauthorized saw the classified documents. We know that after classified material 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 place. Claims he retained classified documents from the White House began circulating even as he moved out in January 2021. The first public evidence of classified information at Mar-a-Lago waited until January 2022 when the initial docs were seized, and the recent search warrant trailed that by eight months. If the FBI thought classified material was in imminent danger from one of America's adversaries, they might have acted with a bit more alacrity.

The real money-maker in the classified world is exposure, and here we finally have a clear leader. Clinton wins in that her exposure of classified emails was done consistently over a period of years in real-time. Her server was connected to the internet, meaning for a moderately clever adversary there was literally a wire between her computer with its classified information and the Kremlin. 

Her server held at least 110 known messages containing classified information, including email 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? Clinton’s security certificate was issued by GoDaddy.

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Whether anyone unauthorized got a look at Trump’s or Biden’s stash remains unclear, but we know for near-certain Clinton’s was compromised. And by compromised we mean every email the secretary of state sent wide open and read, an intelligence officer’s dream. 

Clinton had no 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 zero seconds to see she was using an unclassified server, and half a tick or two to hack into—hostile actors gained access to the private commercial email accounts of people with whom Clinton was in regular contact. Extremely valuable to the adversary were the drafts, documents in progress, a literal chance to look over Clinton’s shoulder as she made policy concerning their country.

No search warrant was exercised to seize the server, and Clinton was taken at her word when she said there was no chance of compromise. So enjoy the bread and circuses around two old men with irresponsible staff or irresponsible ambitions who got caught with classified information improperly stored. The real damage had already been done years earlier by Clinton, who escaped any penalty, not even the temporary embarrassment of a special prosecutor.