Photo: NICHOLAS KAMM/AFP via Getty Images

In 2002, with his cultural stock at an all-time high after calmly navigating an American tragedy, Rudy Giuliani leveraged his post-9/11 standing to form a security consulting firm that lent its services to esteemed clients like the Qatari Interior Ministry, OxyContin-maker Purdue Pharma, and noted drug smuggler and data miner Hank Asher. Because of this work history — and because he reportedly thought Giuliani didn’t have the “stamina” to actually join the Cabinet — Trump brought in Giuliani to serve as a cybersecurity adviser in the early days of his administration.

The president is quite fond of appointing underqualified candidates for lifetime judicial appointments, or bringing in Cabinet-level officials who’ve spent their business careers in opposition to the service their department is meant to protect. In this spirit, Giuliani made an excellent Trump choice: The cybersecurity adviser forgot the six-digit code to unlock his phone.

According to a report from NBC News, in February 2017 — less than a month after becoming Trump’s cybersecurity adviser — Giuliani visited an Apple Store in San Francisco because “he had forgotten the passcode and entered the wrong one at least ten times.” A former store employee who saw the incident told NBC News that it was “very sloppy.”

Managing passwords is a burden of the computer age and one that Giuliani shouldn’t necessarily be condemned for. But actual cybersecurity analysts told NBC News that the real concern was that Giuliani sought help at a highly trafficked public store. “There’s no way he should be going to a commercial location to ask for that assistance,” E.J. Hilbert, a former FBI agent for cybercrime and terrorism, told NBC’s Rich Shapiro. “It’s unnerving to think that this individual has access to the most powerful person in the world and that sensitive communications could be disclosed to people who should not have access to them,” added former FBI agent Michael Anaya.

Trump, however, may not have minded the lapse in phone security. As late as October 2018, Trump was still using his personal iPhone, which allowed Russian and Chinese intelligence to listen in as he called his advisers. He’s also left behind his phone in a golf cart, causing Secret Service to “scramble” to retrieve it.

Though the Apple Store incident occurred nearly three years ago, it appears that Giuliani hasn’t learned his lesson. Last week, NBC News reported that America’s Mayor had butt-dialed a reporter twice, leaving messages in which he discussed with an unknown associate his need for “a few hundred thousand” for business dealings in Bahrain and Turkey.