Diligent Enterprise Management, LLC v. AML Global Eclipse, LLC, DWC Pine Investments I, Ltd., Alan Klapmeier, James Carroll, Steve Serfling, RJ Siegle, and Mike Wyse

District Court, S.D. New York·Decided March 3, 2026·No. 1:24-cv-02228·Unknown

Opinion

USDC SDNY DOCUMENT UNITED STATES DISTRICT COURT ELECTRONICALLY FILED SOUTHERN DISTRICT OF NEW YORK | DOC #: DATE FILED: _ 3/3/26 DILIGENT ENTERPRISE MANAGEMENT, LLC, 24-CV-2228 (VEC) (BCM) Plaintiff, OPINION AND ORDER -against- AML GLOBAL ECLIPSE, LLC, DWC PINE INVESTMENTS I, LTD., ALAN KLAPMEIER, JAMES CARROLL, STEVE SERFLING, RJ SIEGLE, and MIKE WYSE, Defendants.

BARBARA MOSES, United States Magistrate Judge. Now before the Court is the application of defendant AML Global Eclipse, LLC (AML) for an award of $163,107 in attorneys' fees and $1,542.54 in expenses, pursuant to Fed. R. Civ. P. 41(d), to be paid by plaintiff Diligent Enterprise Management, LLC (Diligent) as a sanction for voluntarily dismissing Diligent Enterprise Management, LLC v. AML Global Eclipse, LLC et al., No. 1:23-CV-10924 (VEC) (Diligent J), and then filing this lawsuit (Diligent I) "the same day against many of the same defendants asserting the same claims." Diligent Enter. Mgmt., LLC v. AML Glob. Eclipse, LLC, 2025 WL 1502032, at *10 (S.D.N.Y. May 27, 2025). For the reasons that follow, AML will be awarded $80,525 in attorneys’ fees and $1,542.54 in expenses. I. BACKGROUND I assume familiarity with the factual background and procedural history of this case, which are described in detail in Diligent, 2025 WL 1502032, at *1-4, and are reviewed here only to the extent necessary to resolve the pending fee application. A. Factual Background Diligent's claims in this Court relate chiefly to a series of agreements, including an Intercreditor Agreement, between defendant DWC Pine Investments I, Ltd. (DWC) and Citiking

International US LLC (Citiking), concerning their rights with regard to certain nonperforming loans issued by affiliates of ONE Aviation Corp. (ONE Aviation). See Diligent, 2025 WL 1502032, at *1. On October 9, 2018, ONE Aviation and its affiliates (the Debtors) filed voluntary Chapter 11 petitions in the United States Bankruptcy Court for the District of Delaware (the Bankruptcy Court). Id. at *2. Two years later, on November 20, 2020 – after a failed Plan of

Reorganization and several aborted sale efforts – the Bankruptcy Court approved the sale of the Debtors' assets to AML, which also agreed to buy the Debtors' secured debt, including a second tranche of nonperforming loans, from DWC. Id. at *3. Citiking appealed the approval order and unsuccessfully sought a stay pending appeal. The bankruptcy proceeding was then "converted from Chapter 11 to Chapter 7." Id. In the Bankruptcy Court, Citiking objected to the allowance of any claim asserted by AML, arguing – among other things – that DWC and AML had conspired to deprive Citiking of its right to credit bid the amounts that the Debtors owed it, and that the sale of the secured debt to AML violated Citiking's right of first refusal pursuant to the Intercreditor Agreement between DWC and Citiking. Id. On June 23, 2023, Citiking withdrew its objection in

exchange for $950,000. Id. B. Procedural History On July 20, 2023, Diligent, as assignee of Citiking, filed Diligent I in New York State Supreme Court. In its complaint, Diligent asserted claims against AML, DWC, and six former directors and officers of ONE Aviation,1 for breach of contract, tortious interference, civil conspiracy, and breach of fiduciary duty, all premised on defendants' "wrongful and deceptive conduct with respect to the bankruptcy and asset sale and purchase of One Aviation." Diligent I

1 The individual defendants sued in Diligent I were Alan Klapmeier, James Carroll, Steve Serfling, RJ Siegle, Mike Wyse, and Carol Larotonda. Compl. (Dkt. 1-1 to Dkt. 1-4 in Diligent I) at 2; see also id. ¶¶ 1-9, 90-146. On December 15, 2023, defendants removed the case to this Court. (Dkt. 1 in Diligent I.) On January 19, 2024, the Hon. Valerie E. Caproni, United States District Judge, gave the parties a briefing schedule for (a) Diligent's planned motion to remand the case to state court, and (b) defendants' planned cross-motion to transfer the case to the District of Delaware, where the

ONE Aviation bankruptcy proceeding was venued. (Dkt. 13 in Diligent I.) In the same order, the district judge extended defendants' time to answer or move against the complaint until "twenty days after the Court resolves the parties' jurisdictional and venue-related issues." Id. In February and March 2024, the parties filed their moving and opposition briefs as to those motions. Additionally, during that period, the parties stipulated to dismiss all of plaintiff's claims against Larotonda. (Dkt. 20 in Diligent I.) Then, on March 12, 2024 – before the reply briefs were filed as to the remand and transfer motions – Diligent voluntarily dismissed its claims against AML and the remaining individual defendants, without prejudice, pursuant to Fed. R. Civ. P. 41(a)(1)(A)(i). (Dkt. 25 in Diligent I.) On March 15, 2024, Diligent voluntarily dismissed its claims against DWC

as well. (Dkt. 26 in Diligent I.) That same day, Diligent filed a "substantively identical" complaint in New York State Supreme Court, Diligent, 2025 WL 1502032, at *4, naming all of the same defendants (except for Larotonda) and asserting the same causes of action. See Diligent II Compl. (Dkts. 1-1 and 1-2) ¶¶ 1-8, 89-152. On March 19, 2024, AML asked Judge Caproni to address the "impermissible chicanery that Plaintiff [Diligent] is engaging in to evade this Court's jurisdiction over the pending motion to remand and cross-motion to transfer." (Dkt. 27 in Diligent I, at 1.) AML suggested that this Court issue "an injunction against the state court action to preserve its own federal jurisdiction." Id. at 2. Judge Caproni held a conference on March 22, 2024 (see Dkt. 28 in Diligent I), but did not issue an injunction. On March 25, 2024, defendants removed Diligent II to this Court (Dkt. 1), where it was assigned to Judge Caproni. On April 24, 2024, Diligent notified the Court that "it [was] unable to proceed with this lawsuit at this time," and requested leave to dismiss Diligent II without prejudice,

pursuant to Fed. R. Civ. P. 41(a)(2). (Dkt. 11.)2 On June 4, 2024, after briefing, Judge Caproni denied Diligent's request and gave it a deadline of June 14, 2024, to "either (a) file a notice of voluntary dismissal with prejudice, or (b) file a letter proposing a jointly-agreed upon briefing schedule to address the threshold service, jurisdiction, and venue issues." (Dkt. 17 at 4.) Plaintiff failed to comply with that order. Instead, on June 14, 2024, Diligent's counsel filed a motion to withdraw, citing "irreconcilable differences," as well as Diligent's failure to pay its legal bills. (Dkt. 19.) Judge Caproni granted the withdrawal motion on June 24, 2024. (Dkt. 23.) On September 6, 2024, after new counsel appeared for Diligent (Dkt. 26), it moved to remand Diligent II to state court. (Dkt. 44.) On September 17, 2024, defendants cross-moved to

transfer Diligent II to the District of Delaware. (Dkt. 47.) That same day, AML, joined by defendants Klapmeier, Carroll, Serfling, Siegle, and Wyse (the Individual Defendants) filed a motion for sanctions and costs pursuant to Fed. R. Civ. P. 11 and 41(d). (Dkt. 50.) On May 27, 2025, after the motions were fully briefed, Judge Caproni denied the remand motion; granted the

2 Under Rule 41(a)(1)(A)(i), plaintiff may dismiss its case voluntarily, by notice, if it does so before the opposing party serves either an answer or a motion for summary judgment.

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Diligent Enterprise Management, LLC v. AML Global Eclipse, LLC, DWC Pine Investments I, Ltd., Alan Klapmeier, James Carroll, Steve Serfling, RJ Siegle, and Mike Wyse, (S.D.N.Y. 2026).

Diligent Enterprise Management, LLC v. AML Global Eclipse, LLC, DWC Pine Investments I, Ltd., Alan Klapmeier, James Carroll, Steve Serfling, RJ Siegle, and Mike Wyse (Diligent Enterprise Management, LLC v. AML Global Eclipse, LLC, DWC Pine Investments I, Ltd., Alan Klapmeier, James Carroll, Steve Serfling, RJ Siegle, and Mike Wyse) — published by Counsel Stack Legal Research, free access to 12M+ legal documents.

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