Rudy Giuliani's Awkward Boomer Move At Mar-A-Lago Party Will Haunt Him Forever

If you're having a bad day, just remember that you're not Rudy Giuliani. Chances are, your mood will instantly improve when you realize you were not the one at Donald and Melania Trump's Mar-a-Lago New Year's Eve bash trying to film the festivities while actually filming your own dazed (and possibly slightly intoxicated) face. Nor did you post it on social media for everyone to see as they rang in 2026. This is exactly what Giuliani did, and the internet had a field day.

Giuliani can be seen frowning at his phone, all nostrils and ginormous teeth, as he tries to film the party. When he did finally manage to flip the camera, the only footage he captured was of his drink. "Rudy's tech skills are about as sharp as his legal advice," one netizen quipped on X (formerly Twitter). "Needs better fitting dentures," another opined. Other users took it upon themselves to turn Giuliani's most awkward facial expressions into memes. Needless to say, the disgraced attorney isn't living this one down anytime soon.

OMG!!! While Zohran Mamdani begins to run NYC, broke and disgraced Rudy Giuliani can't even run his own iPhone. He tried to film the Mar-a-Lago New Year's Eve 2026 party but accidentally flipped the camera on his own dazed face.

This is what rock bottom looks like. pic.twitter.com/qK9wzroSzl

— CALL TO ACTIVISM (@CalltoActivism) January 1, 2026

This wasn't the first time Giuliani showed his incompetence when it comes to technology, however. In 2017, shortly after President Donald Trump appointed him as his cybersecurity advisor, Giuliani broadcast his inaptitude for the job when he managed to lock himself out of his iPhone. He visited an Apple store for help after entering the wrong password over 10 times, leading the device to lock him out completely. The story only broke in 2019, with a former Apple employee telling NBC News, "Very sloppy. Trump had just named him as an informal adviser on cybersecurity and here, he couldn't even master the fundamentals of securing your own device." As a government employee, Giuliani should never have visited an Apple store for assistance, members of the FBI noted.

Rudy Giuliani's disbarment officially made him Donald Trump's worst lawyer, but there are other areas in life where he's also failed to exude excellence, like being a good husband (Giuliani will never live down those affair rumors) and not embarrassing himself on a regular basis. Giuliani's list of gaffes is long and mortifying and arguably overshadows his boomer blunder at the New Year's Eve party.

During his May 2024 arraignment, which took place over Zoom, Giuliani's miserly tech skills led to an embarrassing moment when he failed to mute his mic when he slipped away (or so he thought) to pee. Instead, everyone on the call was obligated to listen in. Awkward. Then there was also the great fart of 2020. Giuliani loudly let one rip — not once, but twice — during a voter fraud hearing in December 2020. He continued speaking as if nothing had happened, but former Trump lawyer Jenna Ellis, who was sitting next to him, gave the game away when she threw some judge-y side-eye his way.

Giuliani also found himself the butt of several jokes when he did a press briefing at Four Seasons Total Landscaping in Philadelphia in November 2020, a few days after the presidential election. Many reporters initially showed up at the Four Seasons Hotel, which was a much more sensible location, given it was close to the center where the votes were getting counted. In the aftermath, many speculated that organizers had made a mistake booking the venue. Giuliani was left doing his press briefing (and getting the news that Trump had lost the election) in front of a dilapidated backdrop, with a crematorium and a sex shop located right across the street. Rock bottom took on an entirely new meaning that day.