The FBI can’t stop the leaking in Trump’s White House.

Neither can the Department of Justice, or the presidential communications team or even new Chief of Staff Jim Kelly. Why? Because the more heavy-handed tactics Trump and his cabinet seek to employ to stop leaking, the more leaky the White House will get.

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Trust me on this one. The music industry really isn’t that different than politics — secrecy is tantamount to everything, except for when it’s not, which is all the time. Between the bragging egos and the incompetent middle managers, the silent observers, squealers, and backstabbers, covering music and politics isn’t a matter of uncovering confidential information — it’s much more like playing air traffic control to a nonstop stream of leaked intel and rumors, making sense of which rumors to ground and which to clear for takeoff.

Why do people leak? There’s ego, jealousy and deceit, but those type of leaks typical carry a lot of baggage. My job is to understand people’s motivations when it comes to leaking, so I find the most reliable people are the ones motivated by a sense of self-righteousness. People who don’t like what they are seeing behind-the-scenes feel that no one is listening to their concerns. They leak information because they think they can affect change. For some people it’s a last resort — for others, it’s a shortcut around red tape and bureaucracy.

That’s why cracking down on leaking never works — it just makes people more desperate and emboldened.

And let’s face it — the likelihood that a leaker gets caught is still relatively small. If you’re smart, and work with competent media that use basic best practices to protect you, the chances that authorities could build a case against you for leaking is relatively small.

So how do you leak sensitive information without getting caught and getting fired or thrown in jail? Below are five things to think about before setting upon your righteous duty to set information free.

Don’t Steal Documents — Photograph Them With Your Phone

Every time you print a document, forward an email or call up a report, you create a digital record. Printer logs and email server reports have brought down more leakers than all the spies in the KGB.

Want to leak a sensitive document? Take a picture of it with your phone and hide and encrypt the image until you’re in a safe location to transmit. Be careful that no one sees you taking a picture with your phone, and make sure to remove geotags and time stamps from your photos (this article tells you how). More importantly, don’t store any sensitive photos in your phone’s default photo album. Protect all sensitive photos and videos in an encrypted app-based vault, like Securepad or Safe Camera.

It also doesn’t hurt to understand how ISP numbers work (this article explains what they can tell you) and how VPNs and Tor Browsers can make it more difficult to trace you online. News outlets like the Washington Post use Onion Routers and encrypted tools like SecureDrop to create virtual safe houses for collecting and distributing sensitive information.

“There are no third parties involved in SecureDrop,” Trevor Timm of the Freedom of the Press Foundation, explained in a WaPo tutorial.  “So the government can’t secretly subpoena Google for the news organization’s information, or they can’t secretly go to AT&T and get any information on SecureDrop. They would have to subpoena the news organization directly, who can fight it and refuse to comply.”

Work With Competent Media Outlets and Insist on Protection

The worst thing you can do with leaked intel is to blast out an email to a bunch of reporters you don’t know and hope that one of them bites. Do your research.

Look for reporters who work for respected news organizations that have a background in investigative reporting and the resources to defend themselves in court. If you leak something to a basement blogger who can’t afford a lawyer to fight off a subpoena, you better hope that blogger is willing to go to jail for 18 months to protect your identity (spoiler alert: they probably aren’t).

But be warned, even if you work with a trusted outlet, mistakes still get made that lead to people getting arrested. Reporter Glenn Greenwald’s news site The Intercept published several classified documents it had been anonymously given showing that Russian spies sent spear-phishing emails to more than 100 local election officials just days before last November’s presidential election. The documents proved to the public that Putin had tried to infiltrate voting systems in key battleground election states. But the documents also showed something else that few people could see — tiny yellow watermarks that are almost impossible to the naked eye.

“Most new printers print nearly invisible yellow dots that track down exactly when and where documents, any document, is printed,” security expert Robert Graham explained in an in-depth post. “Because the NSA logs all printing jobs on its printers, it can use this to match up precisely who printed the document.”

NSA contractor Reality Winner was arrested and charged with violating the Espionage Act and is facing ten years in prison. Many criticized The Intercept for lax security precautions that exposed Winner to arrest. (Many more criticized Trump and the DOJ for trying to keep the Russian news secret in order to protect their man in Moscow.)

The lesson in all this — take control of your personal security. Make sure you have an understanding of how the media is going to use your information and documents. Explicitly ask reporters how they plan to use the information you’re providing them — are they going to paraphrase it, are they going to quote it or are they going to make copies available to readers for download? And ask them how they are going to refer to you in their story? How will they describe your role, and how will they describe how they obtained the information? When it doubt, ask questions and advocate for yourself because once the story is published, you’re generally on your own.

When in Doubt, Only Communicate Verbally (And Make Sure You’re Not Being Recorded)

When you hand over documents to news outlets, you cede control of those documents and how they are used. Not only does that create a digital paper trail, but it’s nearly impossible to claw back a document once it’s been released into the public domain.

When possible, try to communicate verbally, preferably over the phone. Make sure you ask the reporter, each and every time, “are you recording me?” and “are we off the record?” If a document is too sensitive to share, read it to him or her over the phone or meet in person and show it to them, allowing them to take notes but not taking it with them. Of course, be extremely careful about meeting anyone in person where you might get caught. Starbucks and coffee shops are the WORST place to be discrete. Everyone drinks coffee and are constantly coming in and out. I recommend a corner in a crappy fast food restaurant or the back of an empty diner. You’re not there for fine dining — you’re there to blow up the system.

Don’t Compromise or Conspire With Other People

Don’t tell other people what you’re doing (besides your spouse, in case you get caught). Don’t try to recruit people you work with. Don’t take it upon yourself to flip confidential informants or radicalize people to your agenda. Most importantly, never, ever, under any circumstances use someone else to unwittingly help you leak a document. Don’t ask for someone’s login so you can pull down a file or ask them to print something that you later plan on turning over to the media. That is wrong, and extremely unethical. Besides, involving other people just creates more openings for you to get caught.

Whistle-blowing is a one-person operation. Do it with pride, do it with a sense of duty to country, and most importantly, do it by yourself!

Understand how Information Flows Toward the Public Domain

This is more of a justification than an actual tip, but I hope it inspires truth-seekers in their pursuit. Know this — information, in its natural state, flows freely toward the light. Unlike objects, animals, minerals and even people, once information has been made public, it can’t be put back into a box. It can not be deleted from the public domain. There’s no unknowing what is known.

Secrets, classifications and other barriers that seek to hide information are temporary and fragile. You might not be able to break out of a prison or escape from a heavily locked cage, but all it takes to free information is for one person to be brave enough to tell the truth. And once that information is liberated, it can’t be constrained.

You, on the other hand, can be constrained for sharing classified information and proprietary secrets. You can go to a jail for decades, have your possessions taken away and your life ruined if you chose to go down this path. Despite the protections in place, most high profile whistleblowers who get caught spend time in jail, see their relationships end and their careers ruined by telling the truth. Before you decide to take this step and become a leaker, think through the consequences, consider what you have to lose, and have a plan in place to protect yourself. With a little smart planning, and a few safety cautions, you should be able to set the world afire without getting burned.


Dave Brooks
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Dave Brooks

Founder & Executive Editor at Amplify Media
Dave Brooks has over 15 years experience as a writer, including eight years as the Managing Editor of Venues Today. He started Amplify in 2014 to give the industry its own voice and turn up the volume on live entertainment.
Dave Brooks
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