The many tech fails of cursed muppet Rudy Giuliani

It’s a tale as old as time. A desiccated muppet valiantly struggles through tech fail after tech fail to eventually be anointed as Donald Trump’s cyber czar and, maybe, finally have a chance at becoming a real boy.

However, in the Grimm’s Fairy Tale that is life, we are sadly deprived of that happy ending. You see, when it comes to all things technology related, Giuliani was cursed to live out his days as a moron. 

We are reminded of this fact today by the somehow unsurprising news that back in 2017, shortly after Trump named him , Giuliani waddled into an Apple Store to have his iPhone restored to factory settings. Why? Because he too many times in a row.

This, dear reader, was not Giuliani’s first tech-related mishap. And no fairy tale, even one as dark is this, is complete without a detailed recounting of its villain’s fall from not-quite grace. 

So let’s take a moment to flip back through the pages of that sad, tech-fail ridden life.

1. The butt dial

Image: NICHOLAS KAMM / GETTY IMAGES

When you’re already down in the dumps, it somehow makes sense that it’s your butt that does you in further.

Giuliani learned this lesson first hand on Oct. 25, when NBC News reported that the former mayor had butt dialed a reporter. In the process, he managed to leave a three-minute message in which he could be heard saying “The problem is we need some money” (among other things). 

2. The tweet invader

Image: The Washington Post / getty 

Like the demented prince of a plague-ridden kingdom, Giuliani felt the need to protect his digital fiefdom from invaders. 

He made that much clear back in 2018 when, after accidentally tweeting out a nonsense link, someone registered the link and turned it into a website trashing Tump. 

Image: screenshot / twitter

However, instead of realizing the folly of his ways, Giuliani insisted that the fault lie not with him. Instead, he proclaimed, “Twitter allowed someone to invade” his tweet. 

3. The website

Image: NBC NewsWire / getty 

Cast your mind back to January of 2017. Giuliani has just been appointed Trump’s cybersecurity advisor, and people were genuinely curious what technical chops he brought to the round table. And so, as one might expect, security experts took a look at his company’s website. 

What they found was anything but reassuring.

But hey, every self-deluded hero’s journey involves repeated demonstrations of incompetence. 

4. The screen reveal

Image: screenshot / fox news

Nothing disputes accusations of idiocy more than thoughtlessly flashing the contents of your smartphone on national television. 

And yet, during a Fox News interview addressing the lawyer’s role in the Ukrainian scandal, Giuliani did just that. 

5. It’s not me, it’s…

Image: Jabin Botsford / getty

“You”

Like a sputtering automaton desperate to find the few remaining others of his kind, the lugubrious Giuliani tweeted those three letters in the summer of 2018. 

Perhaps he was hoping for some kind of human connection, or maybe attempting to fulfill a dark prophecy, but either way he reminded everyone just how far he had managed to not come over the years.  

Like many a failed Disney villain before him, Giuliani never truly learned his lesson — and his repeated tech fails kept him trapped in his muppet-body prison. As is the way of these tragic tales, the once mayor of America is doomed to live the rest of his life never knowing the pleasures of being a real, live boy.