Will Rudy Giuliani End Up Homeless?

Mike Weisser
4 min readDec 5, 2023

I’ve told this story before but it’s worth telling again. Back in 1987, I flew down to D.C. for a meeting, rented a car at National Airport and was now stopped at a red light on Wisconsin Avenue in the Georgetown section of the city.

While I was waiting for the light to change, an elderly man wearing a raincoat and a hat (it was raining that morning) shuffled across the street in front of my car. He was holding a quart of milk in one hand and in the other hand he had the leash attached to a small dog. Obviously, he had been sent to the deli to get milk for the morning coffee and also to give the dog a chance to pee.

All of a sudden — holy shit! — that old man was none other than John Mitchell, former Attorney General, who was now a convicted felon living rent-free with some little, old lady in her Georgetown townhouse, and in exchange for running little errands, he had a place to sleep.

So, I’m sitting there in my rented car, looking at the man who had once been the second most powerful person in the United States and was now one step away from being just another street-corner bum.

Know how they say that anyone can rise all the way to the top in the United States? Anyone in the United States can also sink to the bottom — social mobility in this most mobile and democratic society of all time works both ways.

I was reminded of this incident yesterday when the judge overseeing the trial of Rudy Giuliani for defaming two Georgia election workers, characterized Rudy’s final attempt to get out from underneath what will be a huge financial loss as ‘nonsense’ and ordered the trial to begin next week.

In fact, Rudy has already been found guilty of consciously lying about what these two women did or didn’t do in collecting completed election ballots in 2020, so this trial is simply going to set how much money the two women will receive.

The two Georgia women, a mother and daughter, are seeking between $15 million and $43 million for both compensatory and punitive damages, and if I know anything about civil law, there is really no limit to punitive damage amounts, so what Rudy will owe these two women could be even more.