The Security Woes of Former President Trump



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Presidents, Prime Ministers, Popes, and I assume even the Dalai Llama, are all headaches for security personnel. Leaders, oftentimes, demand the flexibility to use technology and handle sensitive material as they see fit while being constant targets for those who wish to do them harm or steal state secrets or simply hack into their lives in some way.


A solid approach to security typically has three pillars that act as the overarching umbrella for how we implement solid protection of people, assets, and information. Physical safeguards ensure that there are barriers to overcome so an attacker cannot simply walk up to the target and shoot, or walk into a building and steal classified information. Technical safeguards ensure that electronic threat detection is in place, whether it’s cameras watching the physical security or firewalls to stop hackers from breaking into wherever the sensitive data is stored. Finally, administrative safeguards ensure that proper policies and procedures, along with management of everything, are in place so that security personnel do not miss anything and that information is handled with the care they need. While this is a very high-level explanation of security, it’s important to understand how we use this very basic framework to ensure that we don’t find ourselves compromised in some way.


In the case of former President Trump, his administration tended to follow along with his maverick leadership style which makes me speculate that the army of security personnel around him were given lifetime prescriptions of Xanax. Security has flexibility, but it also requires rigidity to a certain extent. Undoubtedly, this president was more of a challenge to secure than previous office holders, though to be fair all presidents are a challenge in their own way.


In that vein, and in light of the recent events at Mar-a-Lago, I thought it would be a good idea to put into context the multitude of security issues that former President Trump brought to the table given who he is as a person and how he typically operates.


So here are some of the core highlights –serious and minor– of the security headaches that we in the security and cybersecurity communities were all discussing while these events received minimal coverage in the news or had a non-security framing.


To start, Trump, right after being sworn into office, still refused to use the government-issued secure mobile phone offered by the Secret Service and instead used his personal phone. His phone is incredibly hackable compared to the hardened versions of mobile phones that the national security apparatus creates to keep our leaders secure. For the record, former President Obama also balked when it was requested he give up his personal Blackberry, but he did compromise and let cybersecurity personnel heavily modify, secure, and restrict its use due to the intense concerns of the President of the United States being arguably one of the largest targets for hacking in the world. By the end of the Obama Administration, China state-sponsored hackers were maintaining persistence in their attacks against the White House. That’s according to the Obama White House Cybersecurity Advisor, Michael Daniel, whom I interviewed in 2020. This means that the White House, when President Trump took office, was already a critical and constant target for foreign cyber-attacks.


Trump’s advisor Kelly Anne Conway also caused a security stir in the White House early on in the administration. She was photographed with her mobile phone while sitting on the couch at the White House. The controversy the media picked up was her feet on the couch while she was in shoes. However, we in the security community cringed at the use of consumer-grade electronics in one of the most secure offices in the world as they are much more susceptible to hacking. While former President Trump’s administration wasn’t the first to have these issues, this is still a grave concern for whoever occupies the presidency.


When Trump fired FBI Director James Comey, he invited Russian diplomats into the Oval Office. While that move itself may be debatable in the political sphere, it made the cybersecurity world wince to see a Russian photographer allowed into the Oval Office, along with his electronic equipment. Could
they have taken pictures of anything they shouldn’t have? Could that camera have integrated a wireless capture device? This type of espionage exists as it’s so easy to integrate wireless snooping and cellular devices into virtually anything, including the USB mouse on a computer which is something I spoke at length about with Yossi Applebaum of Sepio Systems when they discovered Chinese intelligence secretly integrating microprocessors into servers that were slated to be delivered to Apple, the U.S. Navy, and others. This was also the same meeting where Trump revealed classified information to the Russian Foreign Minister and Ambassador, which needless to say is why the NSA probably has a dedicated Alcoholics Anonymous meeting just for their personnel.


Japan’s Prime Minister, Shinzo Abe, visited former President Trump at his Mar-a-Lago home early in 2017. During this visit, he ended up talking about a response to North Korea’s most recent missile test with President Trump. This happened in the open air where members of the golf club (read: without security clearance) were also dining. This prompted then-House Minority Leader Nancy Pelosi to tweet: “There’s no excuse for letting an international crisis play out in front of a bunch of country club members like dinner theater.”


When President Trump met with Russian President Vladimir Putin in Hamburg Germany in 2017, he took possession of his translator’s notes and ordered that person not to discuss what had transpired with other U.S. government officials. From a security and transparency standpoint, this is also a violation of the Presidential Records Act. If something was agreed upon by the two world leaders, the U.S. could be at a security disadvantage if the proper security and administration officials are unaware of what may be happening shortly.


Also, in 2017, famed Rock and Country musician, Kid Rock, met with President Trump in the White House along with Sarah Palin, Ted Nugent, and their respective spouses. In a 2022 interview with Tucker Carlson on Fox News, Kid Rock mentioned that the president sought his advice on geopolitical issues. Kid Rock jovially told Mr. Carlson; “We’re looking at maps and s***, and I’m like, ‘Am I supposed to be in on this s***?’ I make dirty records sometimes. ‘What do you think we should do about North Korea?’ I’m like, ‘What? I don’t think I’m qualified to answer this.’” While Kid Rock may be a talented musician, he does not have the proper vetting and clearances to look at “maps and s***” if they relate to sensitive information regarding the nuclear situation in North Korea.


In 2018, President Trump once again met with President Putin in Helsinki, Finland, and made the following statement when asked if the President of the United States believed his own intelligence infrastructure and reporting on President Putin over the allegations of Russian interference in the 2016 elections: “President Putin says it’s not Russia. I don’t see any reason why it would be.”  Statements like this can undermine the confidence in the intelligence community and federal law enforcement which potentially makes it harder for them to release future reports while still maintaining the confidence of the general public. When that trust has been eroded, disinformation can run rampant.


President Trump’s friendliness to the QAnon movement has been considered a national security threat due to the galvanization of domestic violent extremists. As a quick backstory: in 2017, President Trump was taking questions in the State Dining Room where he was hosting a dinner for military commanders and their spouses. Gesturing to the military guests he stated; “You guys know what this represents? Maybe it’s the calm before the storm.” When pressed, the former president did not elaborate. Whatever Trump meant at that moment, this helped to galvanize the QAnon movement (who uses the term “the storm” as a call to overthrow the government) which had been gaining momentum since “Pizzagate.” Pizzagate is where people began to seriously believe that Hillary Clinton and a cabal of other leaders were running a child trafficking ring in the basement of a pizza restaurant in Washington D.C. that didn’t actually have a basement. Since that time, the U.S. has seen multiple acts of violence committed by QAnon supporters and many in the security community believe that President Trump made the situation worse by repeatedly offering subtle support to this fringe conspiracy movement.


The former president was also a prolific Twitter user until he was banned, and in 2019 tweeted out a sensitive satellite surveillance image that showed the results of a disaster at an Iranian space facility. The image that was tweeted out by Trump had a vastly superior image resolution to any known commercially available satellite imagery. Thus, this gave potential adversaries of the United States a serious look into the capabilities of our spying from orbit. Former President Trump had the right to put out this image since he was the president at the time, however, from a security standpoint moves like this are frowned upon. Imagine if I tweeted out the make and model of the firewall I recommend to my clients. That would help build a roadmap for attackers into how I defend anyone I help.


U.S. intelligence officials repeatedly sounded alarms regarding President Trump’s debts to both foreign and domestic entities.  With hundreds of millions of dollars owed to Germany’s Deutsche Bank and others, the national security community is rightfully concerned that those debts could compromise the president. Working for the intelligence community requires, not just background checks, but also financial checks since having a foreign intelligence agency pay off; say, one’s gambling debts in Las Vegas means a possible quid pro quo of U.S. secrets being handed over in an exchange. It’s a very serious security concern and with actual classified material being stored insecurely at Mar-a-Lago, it’s enough to give even the most veteran of agents a serious headache. Though to be clear, at the time of this publication there has been no indictment or charges of Donald Trump personally in this vein. Nevertheless, it’s of grave concern.


Federal law enforcement went on high alert after the 2020 presidential debate when President Trump told the Proud Boys to “Stand back and standby” which the now designated terrorist organization used as a recruiting tool to grow their ranks, thus causing deep concern in the law enforcement and security communities. The Proud Boys have a history of violence in the United States and elsewhere so increasing their numbers is desirable to pretty much no one outside the extremist orbit.


After the horrific events of January 6, 2021, there were grave national security concerns about his two-ish weeks left in office as well. Aside from the physical security breach of the U.S. Capitol that day, there were concerns that his supporters may attempt to violently interfere with the inauguration of now, President Biden. With President Trump being the first surviving president in 152 years to skip his successor’s inauguration there was concern that this would be seen as a signal to extremist outfits to regroup and attempt one last effort to keep Donald Trump in office.


Given this small sampling of some of the security concerns about President Trump’s time in office, it’s not surprising that these issues would follow him out of office.


Mar-a-Lago, his fabled “Winter White House,” is a golf resort that makes it virtually impossible to fully secure with the now reduced Secret Service staff a former president is granted. In 2019, Chinese national, Lu Jing, was caught trespassing and taking pictures at Mar-a-Lago. She was acquitted of trespassing but sentenced to six months in jail for resisting arrest. Even earlier in 2019, Chinese national Yujing Zhang was convicted of lying her way into a restricted area at Mar-a-Lago, lying to federal agents, and possibly carrying malware. Recently, in 2022, it was discovered that little to no checking was done on a woman who was posing as a Rothschild family heiress and got such deep access to the former president and his inner circle that there are pictures of her with Donald Trump, Republican Senator Lindsey Graham of South Carolina and other top officials. Inna Yashchyshyn, posing as Anna de Rothschild, is being investigated by the FBI, Canadian law enforcement, and other agencies.


National Security exists for a reason. The United States being, arguably, the most powerful country in the world means that we have various secrets to protect and protocols to ensure that our most valued information doesn’t fall into the wrong hands, whether it be accidental or deliberate. There are thousands of men and women dedicated to protecting this apparatus daily. They are trained to look for patterns of compromise or malfeasance over time to help identify if there are leaks, hacks, spies, or worse that are attempting to undermine our security. When the warrant was served on August 8, 2022, to the former president, it wasn’t a surprise to us security professionals that have been paying attention to how our former maverick president operates. I just hope the FBI and Department of Justice determine that we are still fully secure. We’ll see.


Nick Espinosa

An expert in cybersecurity and network infrastructure, Nick Espinosa has consulted with clients ranging from small business owners up to Fortune 100 level companies for decades. Since the age of 7, he’s been on a first-name basis with technology, building computers and programming in multiple languages. Nick founded Windy City Networks, Inc at 19 which was acquired in 2013. In 2015 Security Fanatics, a Cybersecurity/Cyberwarfare outfit dedicated to designing custom Cyberdefense strategies for medium to enterprise corporations was launched.

Nick is a regular columnist, a member of the Forbes Technology Council, and on the Board of Advisors for both Roosevelt University & Center for Cyber and Information Security as well as the College of Arts and Sciences. He’s also the Official Spokesperson of the COVID-19 Cyber Threat Coalition, Strategic Advisor to humanID, award-winning co-author of a bestselling book, TEDx Speaker, and President of The Foundation.


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