Rudy Giuliani's bankruptcy saga is nearing a conclusion as a U.S. judge hinted at likely dismissing the case. The move could drastically impact the former New York City mayor and Donald Trump lawyer, who was ordered to pay $148 million to two Georgia election workers for defamation.

Judge Sean Lane of the U.S. Bankruptcy Court for the Southern District of New York indicated on a Wednesday hearing that he is leaning towards dismissal. Lane noted that ongoing issues with Giuliani's financial transparency hampered progress. A final decision is expected on Friday.

The bankruptcy case has been tumultuous, marked by disputes over missed deadlines and accusations that Giuliani is manipulating the legal system to delay paying his debts. His creditors, led by ex-Georgia election workers Ruby Freeman and Wandrea Shaye Moss, argue that Giuliani is using the bankruptcy as a pause button on his numerous legal challenges.

Giuliani initially sought Chapter 11 protection to reorganize his finances, but later requested a shift to Chapter 7 liquidation, suggesting that a trustee should manage and liquidate his assets. However, he quickly pivoted again, pushing for a complete dismissal instead. His legal team contends that administrative fees in a liquidation would consume a substantial portion of the assets.

Dismissal would permit Freeman and Moss to resume their efforts to collect the defamation award, notably by reviving their case in Washington D.C., thus avoiding additional bankruptcy court fees. However, it would leave Giuliani open to further legal scrutiny and asset seizures.

I'm leaning towards dismissal frankly because I'm concerned that the past is prologue, said Judge Lane at the hearing, emphasizing issues of financial transparency.

The dismissal wouldn't eliminate Giuliani's debts. His creditors could seek other legal avenues for repayment, such as acquiring court orders to seize his assets, including his apartments and other properties. They could also continue defamation, harassment, and other claims that the bankruptcy had paused.

Giuliani filed for bankruptcy last December under a deluge of legal woes, including a disbarment decision and multiple lawsuits tied to his efforts to overturn the 2020 presidential election. In his filings, he reported nearly $153 million in existing or potential debts. Conversely, his assets were estimated between $1 million and $10 million, including a significantly diminished retirement account that forms a critical part of his financial portfolio.

Giuliani's legal team, represented by the firm Berger, Fischoff, Shumer, Wexler & Goodman LLP, and the creditors' committee, represented by Akin Gump Strauss Hauer & Feld LLP, remain embroiled in legal tactics. Giuliani's pivot on the bankruptcy underscores the tension between hastening a resolution and ensuring creditors retrieve as much debt repayment as possible.

Insight into Giuliani's financial maneuvering reveals skepticism. Freeman and Moss' attorney, Rachel Strickland, accused him of engaging in the bankruptcy process as a bad-faith litigation tactic. Judge Lane also rebuked Giuliani during the hearing for interrupting proceedings.

The implications of Lane's upcoming decision are far-reaching, potentially setting precedents for personal bankruptcy claims intertwined with complex legal liabilities and political undercurrents. For now, Giuliani's financial and legal turbulences remain a focal point of keen scrutiny.