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The Two Biggest Losers: Trump and Giuliani

Trump Giuliani

Rudy Giuliani was never well-liked. And he was clearly racist before all the clear evidence came in; when he cracked down on low-level crime during his tenure as New York City mayor, which meant arresting an unnecessarily large number of people of color. His policy was later determined to be racially-biased.

That’s why he’s the perfect dogmatist to lead Trump’s current efforts to disenfranchise Black voters. The dogma fits his deranged bulldog persona. He’s always tried to convey an image of toughness melded with bluster — sound familiar? But in the end, it really was just a delusion from a truly detestable individual. Again, sound familiar?

Before 9/11, most New Yorkers had had enough of Giuliani, and then after the terrorist disaster, when admittedly he showed fortitude, people for a time respected him. Not for long though. Pulling a stunt out of the Trump playbook, he tried to have the 2001 mayoral election pushed back so he could stay in power, illegally, for a third term. Cooler and more legal heads prevailed, and Mike Bloomberg was elected, and he did two things that Rudy couldn’t do —scheme his way, legally via money, to a third term and pull the city back together after the attack.

The question now is, who is going to put Giuliani back together? Or is he too far gone? He marketed himself at the start of his political career as a tough U.S. Attorney who fought the mob. Little did we know he would later become the underboss to the Don. His only other self-fulfilling fantastical gambit was when he shoehorned himself into becoming the 26th player on the New York Yankees 25-man roster after 9/11, and that relationship has since soured when he was booed ferociously throwing out a first — and last — pitch.  

The only thing I can remember that made me like him just a tiny bit was after the separation from his second wife, Donna Hanover, Rudy bunked with a gay couple in their Midtown apartment. Was he an intolerable tolerable? That was in 2000 before 9/11. Hanover found out about the separation when Rudy mentioned it during a press conference, apparently while he was part of the platonic gay throuple and publicly and shamelessly dating Judith Nathan, who would become his third divorced wife. He fancies himself as quite the ladies’ man.

And that was clearly apparent in his now iconic turn in a vomit-inducing scene from the new Borat movie. Rudy disgustingly hitting upon a pseudo teenage reporter (played by an actress in her late 20s for those who don’t know). And then, going into a bedroom, lying aross a bed, and manhandling himself in her presence. It wasn’t embarrassing — it was hideous and revolting.

Now Trump has put Rudy in charge of his illegal revolt against the United States electoral system, tapping Yoda Rudy as his lead counsel. The insanely insecure and desperate sore loser hates losers. Trump must hate himself because he is loser number one in the country right now (losing both the popular vote and Electoral College, handily), followed by Rudy at well-deserved second place. Why would loser Trump (can’t say it enough) put the habitually losing Rudy in charge of a loser enterprise to overturn election results?

Rudy’s 2008 run for the presidency was a major flop, and since that loss, Rudy has been at a loss at trying to win in government again, and mad that his mad-power grabs have been maddeningly ignored.

Then Trump came along, a fellow hair-challenged, retrograde 70-something; a brusque New Yorker who demands bootlicking. Rudy literally saw himself in Trump, and his shot at hitting the big-time. This was his desperate ploy to return to his Big Apple days surrounded by apple-polishers; however, this time, Rudy had to be the boot-licker. He slobbered himself all over Trump who loves to be bathed in suck-up saliva. Rudy’s big mouth was a perfect fit for Trump. And then it wasn’t.

Rudy wanted to be secretary of State, and Trump wanted glamorous gravitas, opting for Exxon's Randy Rex Tillerson. Rudy wanted to be Attorney General, so when Jeff Sessions wouldn’t give lip-service to Trump, Rudy licked his chops. This was his time. He would become Trump’s bulldog Roy Cohn. But Rudy was thwarted again when Trump went with someone with more heft, Bill Barr.

What would Rudy do? Trump’s dictatorship was Rudy’s last opportunity to diabolically dictate to all the minions in government. He longed to be in charge and relevant, and to Trump his relevance only became relevant if he could make Joe Biden, via Hunter, irrelevant. Bloviating and bogus Rudy traveled the world over, cavorting with henchmen, dining with dictators, and sending manila envelopes chuck-full of garbage to the FBI, CIA, and Pompeo. Trump, and Rudy, promised the biggest political scandal in history that embarrassingly disappeared like Rudy’s slippery hands into his pants.

This epic loser is leading the charge for the clear loser of the presidential race. Rudy hasn’t won anything since the Yankees were browbeaten into giving him an ostentatious World Series ring which he never takes off, unlike his wedding rings. This ring banger is barking about nationwide election fraud and being skewed on social media as the real fraud.

Rudy’s being snickered at throughout Pennsylvania, during his recent press conference between a sex shop and a morgue in Philadelphia, by a disbelieving judge in a Williamsport, and by fed-up election officials in Harrisburg. Rudy barnstorming the state claiming without evidence of statewide malfeasance. His rants and hysterics have been hysterical to those he encounters. America’s mayor reincarnated to Pennsylvania’s clown. His laughable arguments only outdone by legendary comic W.C. Fields who joked that his epitaph should read, “I’d rather be in Philadelphia.” Rudy’s epitaph will add “…between a crematorium and a strip club.” So apropos for a guy who’s been disintegrated and sexually humiliated.

If this all wasn’t so incredibly dangerous to our democracy, it would be sad. But no tears for Ribald Rudy. He’s either wildly lost his way or wickedly lost his mind. And it’s both because Rudy has always been the biggest fraud, with the notable exception of Donald Trump. And it’s fitting that as the Titanic that is Trump sinks deeper and deeper into loserdom, Rudy remains on the deck, playing the world’s smallest violin, with no one listening. They will go down into the ash heap of history, not as they wished as titanium and unsinkable giants, but as the world’s two biggest losers. Trump and Rudy’s last hurrah will be one epic fail.

John Casey is editor at large of The Advocate.

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