• Klassified Kapers: Hillary v. Trump

    September 23, 2022

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    Posted in: Democracy, Trump

    Hillary versus Trump in their Klassified Kapers. Both kept classified information at their homes, both appeared to break the law, only one may be legally punished. But which one wins the battle to have done more damage to national security than your average enemy spy?

    In the end when dealing with the damage done by mishandling classified information it comes down to exposure; who saw it, what was it, and when was it seen?

    The “who” part is clear enough; a document left inadvertently on a desk top in an embassy guarded by Marines might be seen by locally hired cleaning staff at worst. A document left on a park bench and seized by the local police risks direct exposure to the host country intelligence services if not sale to the highest bidder depending on the locale.

    The “what” is the real stuff of James Bond and even actual spies. A lot of things are classified, many perhaps 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, but it still might rightly qualify as classified at the Confidential level. It would take a knowledgeable person looking at documents one-by-one to conclude which of the 7 out of 10 were overclassified.

    Other times “what” is classified 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 horsetrade, buying and selling info they pick up along the way about other countries for info they need about theirs. One of the most deeply-run intel operations against the State Department involved a Euro-ally looking for info on a competitor by listening in to third party U.S. diplomatic sites where the data was treated almost as 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 lot who knows tomorrow at midnight the convoy will set forth from A to 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.

    Lastly, we have the unknown factor in judging our contest. Few countries actively harvesting intelligence are in the mood to tell anyone about it. In fact, just the opposite. Even when caught spies deny everything such that one of counter-intelligence’s main tasks after a bad guy is caught is to try and figure out what he likely gained access to, which documents or information he got. Note the “or” there because it is always information, data, which is classified, not pieces of paper. Much damage can be done with a diplomat’s hand written notes of a meeting, unmarked by a classification such as Secret, compared to a document marked Secret but containing nothing really worth keeping quiet. The marking on a document is only the drafter’s best estimate of what the information on paper really is worth. This all makes it hard to judge the relative impact of one exposure to another, but there are other ways.

    So those are the ground rules, on to 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 such that the government recovered over 300 documents with classified markings from Trump since he left office. 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. To be fair, 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 just 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 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. Hillary 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. 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 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.

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

    In this race, the “what” is a toss-up. Little information exists on specifically what each document trove held, though the WaPo 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 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 the classified 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’ed 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 Klassified Kaper. 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 in Mar-a-Lago waited until January 2022 when the initial docs were seized, and the recent search warrant tailed that by months. It suggests 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 alacrity.

    Not so with Hillary. 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. 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? Um, Clinton’s digital security certificate was issued by consumer-level GoDaddy.

    The last bit seals it: we have a winner. Whether anyone unauthorized got a look at Trump’s stash remains unclear, but we know for near-certain Hillary’s was 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 zero seconds to see she was using an unclassified server, and half a tick or two to hack (hostile actors gained access to the private commercial email accounts of people with whom Secretary Clinton was in regular contact) into it. Extremely valuable to the adversary were the drafts, documents in progress, a literal chance to look over Clinton’s shoulder as she made policy.

    Unknown is the actual process Hillary used to move classified material to and from her server from the main State Department and other systems. 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 SysAdm for the home server was a State Department Civil Service employee she hired and so suggests 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. All we can say is some intelligence officer in Moscow or Beijing was probably promoted to Colonel off this one.

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  • Recent Comments

    • Rich Bauer said...


      Talk about beating a dead horseface, LOCK THEM BOTH UP.

      Feel better?

      09/23/22 9:27 PM | Comment Link

    • Rich Bauer said...


      But then, Hillarious never claimed the Feds set her up.

      09/24/22 8:22 AM | Comment Link

    • John Poole said...


      Bauer- I was hoping instead for a rematch in 2024 so I could again abstain. America deserves a tie where both Donald and Hillary copartner and share the POTUS throne. Finally! Peace in the homeland.

      09/24/22 10:19 AM | Comment Link

    • Rich Bauer said...


      Why would Hillary’s emails be in Trump’s possession…unless he was selling them to Russia, hmmmm?

      Asked why federal agents raided his Florida home, Donald Trump floated the idea that they might have been looking for Hillary Clinton’s emails. Speaking to Fox News host Sean Hannity Wednesday night, the former president mentioned his theory alongside the claim that he was able to declassify documents just by “thinking about it.”

      “There’s also a lot of speculation, because of the severity of what they did, the severity of the FBI coming and raiding Mar-a-Lago,” Trump said, referring to the search last month amid claims Trump had improperly retained sensitive documents. “Were they looking for the Hillary Clinton emails that were deleted, but they are around someplace?”

      “They may be saying… They may have thought that it was in there. And a lot of people said the only thing that would give the kind of severity that they showed by actually coming in and raiding with many, many people is the Hillary Clinton deal, the Russia, Russia, Russia stuff, or… I mean there are a number of things. The spying on Trump’s campaign.”

      So it WAS Trump WHO hacked Hillary’s computer.

      09/24/22 11:17 AM | Comment Link

    • Rich Bauer said...


      Russia, Russia…Trump has Hillary’s emails and 100 TS docs if he has to flee to Russia. Of course getting Russian citizenship comes with military service in Ukraine. Eddie Snowden just got his Russkie citizenship and no doubt is headed to the special military operation.

      09/26/22 12:55 PM | Comment Link

    • Rich Bauer said...


      Trump: FBI planted those classified documents at Mar-a-lago. Who is next?

      Court-appointed Special Master Raymond Dearie has now requested that Trump go on record in a sworn declaration regarding the classified documents the FBI recovered. In a filing Thursday, Judge Dearie ordered Trump to submit a sworn declaration itemizing “inventory” of materials seized from his Palm Beach, FL estate that were NOT actually recovered during the FBI search.

      Trump likely will not provide a sworn statement as it is against his religion. Instead, Trump plans to go on FoX the night before the midterms to warn Republican voters to stay home on Election Day to prevent the FBI from planting classified documents in their homes.

      09/26/22 6:02 PM | Comment Link

    • Rich Bauer said...


      “But the real money-maker in the classified world is exposure, and here we finally have a clear leader.”

      Peter may cry wolf, but he has picked up on the perfect Putin payoff plan: Trump was only in it for the money. And if you think Trump would never do something like that, then you probably believe in fairy tales.

      09/26/22 9:52 PM | Comment Link

    • Rich Bauer said...


      “All we can say is some intelligence officer in Moscow or Beijing was probably promoted to Colonel off this one.”

      Wow, Peter knows a wolf in sheep clothing when he sees one. Russian intelligence perhaps.

      Trump could have videoed the TS documents and RETURNED THEN TO THE National Archives, but he kept them…Why?

      As Peter has sensed, perhaps Trump let someone WITHOUT TS SCI CLEARANCE HANDLE THEM. FINGERPRINTS. On POSSIBLE orders of a Russian intelligence officer HE DESTROYED 46 TS docs and left the empty Classified folders. The Folders probably have the incriminating Russian agent fingerprints on them. Perhaps Dumbass didn’t have time to destroy the other TS docs without Secret Service agents aware and boxed them for destruction later.

      Yep, somebody in Moscow got a big promotion off this one.

      09/28/22 12:46 PM | Comment Link

    • ‘Rigged’ election claims then and now | Phil Ebersole's Blog said...


      […] I think the motive for these investigations is to find something – anything – that would discredit Trump or possibly prevent him from running again.  I recall Democrats took a different stance about Hillary Clinton’s problems with handling classified information. […]

      09/30/22 8:22 AM | Comment Link

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