Rudy Giuliani's Trump files could spill out in bankruptcy

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Former Mayor of New York Rudy Giuliani speaks to reporters as he leaves his apartment building in New York on Aug. 23, 2023. (AP Photo/Seth Wenig)

The stakes were already high for former NYC mayor in Rudy Giuliani’s bankruptcy following a $148 million judgment for defaming Georgia election workers, but now his flouting of discovery in the Ruby Freeman and Shaye Moss case is being used as a justification for a far-reaching proposed order complete with discovery demands that threaten to expose the “nature of any legal services that you have performed, or continue to perform, for Donald J. Trump” and much more.

Attorneys for the appointed Official Committee of Unsecured Creditors in the bankruptcy case on Thursday filed a notice of a hearing to take place before U.S. Bankruptcy Judge Sean Lane at 2 p.m. on April 4 on the committee’s motion to allow discovery demands to be served via subpoena on Giuliani and third parties, like his companies, his legal defense funds, his son Andrew Giuliani (the “designated agent” of the Giuliani Defense legal fund), Maria Ryan, and others.

The notice of hearing submitted attorney Philip Dublin of the firm Akin Gump Strauss Hauer & Feld LLP, requiring that “any responses or objections” to the attached motion be “served so as to be actually received by the Court and the Committee no later than March 28, 2024 at 4:00 p.m.,” then turned to the motion’s stated interest in probing Giuliani’s “assets, liabilities, relevant prepetition conduct and financial position.”

The motion pointed out that Giuliani’s massive defamation judgment came about after his “willful shirking of his discovery obligations” lost him the case by default.

In light of that, the attorneys said, “substantial doubt exists” that Giuliani is willing or able to “comply fully with his disclosure obligations” in the resulting bankruptcy case set in the same jurisdiction where he made his name as U.S. Attorney for the Southern District of New York.

“Indeed, it was Giuliani’s discovery misconduct in the Freeman Litigation—concerning Giuliani’s defamatory statements about two Georgia 2020 election workers—that led U.S. District Court Judge Beryl A. Howell to enter a $148 million default judgment against Giuliani,” the motion recounted. “Judge Howell found Giuliani’s misconduct in the Freeman Litigation so egregious that she further ordered immediate dissolution of the automatic thirty-day stay of enforcement of the judgment, allowing the plaintiffs in the Freeman Litigation to take immediate steps to enforce the judgment.”

Because the same “concerns” of an uncooperative Giuliani “persist,” and because Giuliani is “currently the subject of at least nine additional pending litigations or outstanding judgments” threatening upwards of $4 billion” in potential damages, a more aggressive approach is “warranted” here, the filing asserted.

“In the Chapter 11 Case, Giuliani has alleged that he has approximately $10.6 million of assets, which amount is dwarfed by nearly $153 million in liabilities,” the motion said. “Given the magnitude of these liabilities—and considering the pending lawsuits against Giuliani and his businesses seek upwards of $4 billion in damages—Giuliani has substantial motivation to continue his historical pattern of financial obfuscation and discovery misconduct.”

In addition to the Freeman judgment he faces, Giuliani faces lawsuits by Hunter Biden, Dominion Voting Systems, Smartmatic, Noelle Dunphy, Giuliani’s former director of business development who accused him of sexual assault last May. Attorneys for those parties previously entered appearances on the docket.

Urging the judge to be mindful the Giuliani has incentive to “obfuscate assets,” the motion called for further investigation into the “origin” of the Rudy Giuliani Freedom Fund Legal Defense Trust Fund and Giuliani Defense, from which he “received substantial monetary support” over the course of the Freeman and Hunter Biden cases. The committee lawyers want to know if or how those legal defense funds tie into Giuliani’s companies and who the donors are to Giuliani.

“To date, the origin of these funds, the relationships between Giuliani and the donors of those funds, and any historical relationship between those assets and the assets of Giuliani or the Giuliani Businesses have not been sufficiently disclosed,” the motion continued.

The filing added that several asset disclosures to date have been “incomplete or otherwise inconsistent,” whether for vagueness or for valuation discrepancies on New York Yankees World Series rings or even for the use of an incorrect address for his Florida property:

Giuliani discloses lumped categories of assets such as “television etc…,” without sufficient itemization. Similarly, the values listed for certain categories—such as “Jewelry,” which includes among other items, a “diamond ring, 3 yankee world series rings,” and 26 luxury watches—are insufficiently itemized and appear to be undervalued. Giuliani claims a total value of $30,000 for this jewelry; yet a single World Series ring may be valued at upwards of $15,000 in its own right. Likewise, Giuliani vaguely discloses “Uber shares”—with no information as to present value, basis, location of those assets, or even the number of shares. Even the address of Giuliani’s Florida property is listed incorrectly.

Sensing that delay tactics are afoot due to “unresponsive” behavior on the part of Giuliani and the debtor’s attorneys, the committee lawyers claimed “it must obtain the relief requested herein to adequately conduct its own investigation and satisfy its fiduciary duties to its constituency” — including making Giuliani sit for a deposition.

In a proposed order, the committee asked the bankruptcy judge to force Giuliani and third parties, whether identified today or on a later date, to “respond to the Requests and to substantially complete their document productions within 21 days.” The proposal Judge Lane has been asked to approve:

The Committee is hereby authorized, pursuant to Rule 2004, to (a) serve document requests as specified below/subpoenas on, and (b) take depositions of, (i) Rudolph W. Giuliani; (ii) Giuliani Partners, LLC; (iii) Giuliani Communications, LLC; (iv) Giuliani Security & Safety, LLC; (v) Giuliani Group, LLC; (vi) Giuliani & Co.; (vii) Rudolph W. Giuliani PLLC; (viii) WorldCapital Payroll Corporation; (ix) Rudy Giuliani Freedom Fund Legal Defense Trust Fund; (x) Giuliani Defense; (xi) Robert Kiger; (xii) Andrew Giuliani; (xiii) Jake Menges; (xiv) Maria Ryan; (xv) Ryan Medrano; (xvi) Joseph Ricci; (xvii) Ted Goodman; (xviii) Michael Ragusa; and (xix) any other party the Committee identifies as possessing information relevant to its investigation into the Debtor’s assets, liabilities, relevant prepetition conduct and financial position.

Also sought were documents on any contracts “relating to business dealings, advertisements, endorsements or any other sources of income,” whether those contracts involve media outlets or Giuliani’s book “The Biden Crime Family: The Blueprint for Their Prosecution” ticketed for an April debut.

Perhaps most eye-popping of all, the proposed requests demand documents and communications that could shed light on Giuliani’s current or former legal representation of Trump, any claim for unpaid legal fees, and his ill-fated “Russian pawn” defamation lawsuit against President Joe Biden:

12. All Documents and Communications concerning the bases, evidence and work product made in connection with any claims or causes of action that are asserted or assertable by You, including, but not limited to, (i) any claims for unpaid legal fees against Donald J. Trump, (ii) any defamation actions against Joseph R. Biden (iii) any unliquidated and/or contingent claims and causes of action listed in Your Schedules and Statements, and (ii) counterclaims that have been or may be asserted in connection with any pending litigation against You, including, without limitation, the Freeman Litigation, the Biden Litigation, the Dunphy Litigation or the Dominion Litigation.

13. Documents and Communications sufficient to identify the nature of any legal services that you have performed, or continue to perform, for Donald J. Trump.

Read the documents here.