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Rudy Giuliani’s Legal Battles: A Cautionary Tale of Loyalty and Consequences

What once seemed to be the never-ending tale of Rudy Giuliani, formerly “America’s Mayor,” now has a sequel of legal failures and resulting financial burdens, which is nothing less than utterly damning evidence for staunch loyalty toward former President Donald J. Trump.

Giuliani’s attempts to overthrow the results of the 2020 election have devolved into case cascade hell. The latest: he just agreed to fork over a huge sum to settle his bankruptcy case and avoid further probing into his finances. Federal court documents filed in White Plains, New York, indicated that the settlement agreement took place after a judge dismissed his bankruptcy case due to his concealment of income sources and failure to comply with court orders.

This comes after a jury delivered the ruling that Giuliani must pay almost $150 million in damages to two former election workers, Ruby Freeman and Shaye Moss, whom he smeared with lies about the 2020 election. The total financial obligations against Giuliani are now pegged at about $153 million, without any plan in place for repayment.

Several professional and personal setbacks have attended Giuliani’s fall from grace. A disciplinary panel in 2022 recommended that he be disbarred, citing his “frivolous” and “destructive” defense of a baseless claim that President Joe Biden did not legitimately win the 2020 election. According to the Board on Professional Responsibility of the D.C. Bar, “Giuliani claimed massive election fraud but had no evidence of it,” leading it to conclude he forfeited his right to practice law.

What further complicates his legal woes is that, in 2019, Giuliani was under scrutiny for his efforts to extract dirt from Ukrainian officials on Trump’s rivals, which included Joe Biden and his son, Hunter Biden. While his associates, Lev Parnas and Igor Fruman, were charged in 2019, the investigation into Giuliani’s role is still ongoing.

The Giuliani arc from prosecutor-celebrity who took down mob bosses in New York City in the ’80s, to mayor on 9/11, to central figure in spreading lies about the 2020 election is a bracing reminder of what can be the price of blind political loyalty. His recent admission to running through an “alter ego LLC” known as Giuliani Communications opens new legal avenues for creditors to collect what they are owed, further complicating his financial situation.

The woes of Giuliani pile on, and his case becomes, as his legal battles go on, a cautionary tale of how being blind to loyalty and propagating untruths might ultimately lead to a dramatic, public fall from grace.

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