Once upon a time, the following events were regarded as “low” points for Rudy Giuliani:

• Accidentally marrying his cousin and not finding out until 14 years later
• Appearing in a Borat movie with his hands down his pants
• Having a hair dye malfunction in the middle of a televised press conference
• Confusing the Four Seasons hotel with Four Seasons Total Landscaping (a business across from a crematorium and next to a sex shop)
• Farting so much that the flatulence made Saturday Night Live
• Being reduced to hawking gold coins on YouTube
• Shaving in the middle of an airport restaurant

Yes, for the man once known as “America’s mayor,” these were deeply embarrassing events that caused people to repeatedly ask, “What the heck happened to Rudy Giuliani?” But in retrospect, these low points represented, if not high points in Giuliani’s life,* then definitely not the worst things that would ever to happen to him. These days, those could soon involve him quite literally going broke and receiving a prison sentence.

As the Daily Beast writes:

Giuliani is poised to get hit with a multimillion-dollar ruling against him in DC over his baseless accusations of election fraud against two poll workers. After that civil trial concludes, he’ll turn around and begin preparing for a criminal trial in Atlanta, where he’s facing many of the same racketeering charges he once wielded as a federal prosecutor against mobsters in New York. And throughout it all, Giuliani has a long list of creditors, from former associates to contractors, who are also hounding him for money.

For Giuliani, 2023 will likely end in penniless defeat. But 2024 could be even worse—it could actually end with him in prison.

In the case of election workers Ruby Freeman and Shaye Moss, Giuliani has already been found liable for defaming them, with this week’s proceedings determining exactly how much money he should have to pay. The women are seeking between $14 million and $41 million—and based on their testimonies about how the former mayor turned Trump attorney ruined their lives with his vicious lies, it’s not hard to see why.

On Tuesday, Moss told jurors that after Giuliani spread baseless claims about her and her mother, “I was afraid for my life. I literally felt like someone going to come and attempt to hang me and there’s nothing that anyone will be able to do about it.” She added: “I now am very anxious. I have these nonstop anxious sweats. I have a lot of dark moments. I no longer go out. I will not be caught out anywhere alone, ever…. I look totally different; I gained, like, 70 pounds. I stress eat. I cry a lot. I’m just this whole new stressed-out person.” On Wednesday, Freeman read a selection of the messages she received, which included “Kill yourself now so we can save AMMO“ and “I hope the Federal government hangs you and your daughter from the Capitol dome you treasonous piece of shit! I pray that I will be sitting close enough to hear your necks snap.” She told the jury, “My life is just messed up. It’s really messed up all because somebody put me on blast, just tweet my name out to their millions of followers.”

After again defaming the women on Monday outside the courthouse, Giuliani took to his podcast later in the week to scoff at the damages they think he should pay. “They’re seeking $40 million,” Giuliani said, laughing and adding, “Oh yeah.” Of course, it’s highly unlikely that the former mayor has anything close to $40 million in the bank, given that he keeps getting sued for reportedly being a deadbeat and, by his lawyer’s own admission, can’t pay his bills. But that’s not Moss’s or Freeman’s problem.

And speaking of problems, a massive civil penalty will look like a dream compared to what may be coming next for old Rudy. Per the Daily Beast:

…the real danger comes in the latter part of next year, when Fulton County district attorney Fani Willis seeks to put Giuliani on trial along with former president Donald Trump for trying to overturn the 2020 election in Georgia. Giuliani faces years behind bars if convicted of essentially taking part in a shakedown of the state’s election system. And yet, the clear way out already taken by others in the case—flipping and becoming a state witness to help prosecutors nail Trump—pits Giuliani against himself. That’s because he’s openly shown himself to be financially dependent on Trump’s massive fundraising.

Look no further than the $100,000-a-plate “Dinner With America’s Mayor” that Trump hosted at his golf course in Bedminster, New Jersey, in September. Were Giuliani to turn on Trump, as other MAGA lawyers like Kenneth Chesebro and Sidney Powell already have done, the Trump money spigot would instantly dry up. The Giuliani downfall has been slow but precipitous: 2021 was the ruining of his professional reputation, with New York and the District of Columbia suspending his law license for spreading lies and his role in the January 6 insurrection. This year exposed his financial ruin. Next year, it could be prison.

Oh well, couldn’t have happened to a nicer guy. (Giuliani has pleaded not guilty to all charges.)

*For him that would be 9/11, which he literally said last year was “in some ways, you know, the greatest day of my life.”