John Francis Calicchio and Vincent Colabella, as Cotrustees of the Thomas A. Calicchio 2010 Trust Under Agreement Dated May 1, 2020 v. Lisa M. Jackson, Tate Jackson, and Phillip J. Michaels, as the Executors of the Estate of John Calicchio, Deceased

CourtDistrict Court, S.D. New York
DecidedMarch 25, 2026
Docket1:24-cv-05101
StatusUnknown

This text of John Francis Calicchio and Vincent Colabella, as Cotrustees of the Thomas A. Calicchio 2010 Trust Under Agreement Dated May 1, 2020 v. Lisa M. Jackson, Tate Jackson, and Phillip J. Michaels, as the Executors of the Estate of John Calicchio, Deceased (John Francis Calicchio and Vincent Colabella, as Cotrustees of the Thomas A. Calicchio 2010 Trust Under Agreement Dated May 1, 2020 v. Lisa M. Jackson, Tate Jackson, and Phillip J. Michaels, as the Executors of the Estate of John Calicchio, Deceased) is published on Counsel Stack Legal Research, covering District Court, S.D. New York primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

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John Francis Calicchio and Vincent Colabella, as Cotrustees of the Thomas A. Calicchio 2010 Trust Under Agreement Dated May 1, 2020 v. Lisa M. Jackson, Tate Jackson, and Phillip J. Michaels, as the Executors of the Estate of John Calicchio, Deceased, (S.D.N.Y. 2026).

Opinion

| USDC SDNY UNITED STATES DISTRICT COURT NT SOUTHERN DISTRICT OF NEW YORK ELECTRONICALLY FILED DOC #: JOHN FRANCIS CALICCHIO AND VINCENT DATE FILED: 3/25/2026 COLABELLA, AS COTRUSTEES OF THE THOMAS A. CALICCHIO 2010 TRUST UNDER AGREEMENT DATED MAY 1, 2020, Plaintiffs, -against- 24-CV-05101 (MMG) LISA M. JACKSON, TATE JACKSON, AND SS Se ee PHILLIP J. MICHAELS, AS THE EXECUTORS OF THE ESTATE OF JOHN CALICCHIO, DECEASED, Defendants.

MARGARET M. GARNETT, United States District Judge: In 2010, John Calicchio (“John Sr.”) and Thomas A. Calicchio (“Thomas”) set up a trust to benefit Thomas’ wife and descendants. From May 2010 until his death on December 11, 2021, John Sr. served as the trustee. While trustee, John. Sr. did not invest the trust’s funds. He also transferred approximately $3.7 million from the bank accounts associated with the trust. In early 2024, Plaintiffs John Francis Calicchio (“John Francis”) and Vincent Colabella (together, “Plaintiffs”) assumed the role of co-trustees. They allege that John Sr.’s failure to invest the trust’s funds and his withdrawals from the trust accounts breached his fiduciary duty as trustee. Plaintiffs seek over $6 million in damages for this alleged breach. Defendants have moved to dismiss Plaintiffs’ claim pursuant to Federal Rule of Civil Procedure 12(b)(6). For the reasons set forth below, Defendants’ motion to dismiss is GRANTED.

BACKGROUND L RELEVANT FACTS! John Sr. and Thomas entered into a trust agreement (the “Trust Agreement”) on May 1, 2010 to set up trust titled “The Thomas A. Calicchio 2010 Trust” (the “Trust”), with Thomas as grantor of the Trust and John Sr. as sole trustee. Dkt. No. 1-1 at 2. The Trust Agreement authorized the trustee to distribute the Trust’s principal and income to the following three entities: (1) Thomas’ wife; (2) his descendants; and (3) “any charitable organizations added to the class of beneficiaries by the Selector.”? Compl. § 13. In addition, the Trust Agreement endowed the trustee with various administrative powers, including the ability to make loans and retain property. Dkt. No. 1-1 at 25-26. The Trust had at least two different bank accounts: one at First Republic Bank and one at Citi Bank. Compl. □ 26, 27. During his tenure as Trustee, John. Sr. transferred funds in and out of the Trust’s accounts on numerous occasions. Jd. 25. Between 2016 and 2021, John Sr. transferred $2,270,000 into the First Republic Bank account and transferred over $2,072,000 out. Id. 426. During that same period, John Sr. transferred approximately $5,527,800 into the Citi Bank account and transferred over $3,630,000 out. Jd. 27. Plaintiffs allege that these transfers were made “for the benefit of third parties or individuals that were not beneficiaries of the Trust, and/or without informing the beneficiaries.” Jd. § 25. Additionally, while John. Sr. served as trustee, the Trust’s principal did not grow in value. Jd. 938. Plaintiffs attribute this lack of growth to the fact that John Sr. did not “prudently invest[] in a portfolio of securities, including

! The following facts are taken from the allegations in the Complaint (““CompIl.”), Dkt. No. 1, and are assumed true for the purpose of resolving this motion. ? During the relevant time period, Plaintiff John Francis and non-party Amanda Calicchio were Thomas’ descendants. Compl. § 14.

stocks and fixed income.” Jd. 29. They allege that, had he done so, the portfolio would have a present-day value of over $6,000,000. Jd. John Sr. died on December 11, 2021. Jd. § 17. Following his death, and pursuant to the Trust Agreement, Norman Rosner briefly served as trustee. Jd. { 18. Thomas replaced him as trustee and appointed Ann Lackowitz to serve in the role on January 13, 2022. Jd. On January 16, 2024, Thomas removed Ms. Lackowitz and appointed Plaintiff Vincent Colabella as Trustee. Id. 919. On February 1, 2024, Mr. Colabella appointed John Francis (Thomas’ descendant) as Co-Trustee. Jd. § 20. Plaintiffs bring this case in their capacity as co-trustees against Lisa M. Jackson, Tate Jackson, and Philip J. Michaels (together “Defendants”) in their capacity as executors of John Sr.’s estate. Plaintiffs allege that John Sr. negligently breached his fiduciary duty as trustee by “failing to hold and properly invest the Funds, administer the Trust for the purpose and sole use of the beneficiaries, and keep the beneficiaries informed of the Trust’s accountings.” Jd. § 37. They seek to hold liable John Sr.’s estate for this allegedly unlawful conduct and obtain damages incurred as a result. Jd. § 41. Il. PROCEDURAL HISTORY Plaintiffs initiated this action on July 3, 2024. Dkt. No. 1. On September 26, 2024, Defendants moved to dismiss the Complaint for failure to state a claam. Dkt. No. 18 (“Mot.”). On October 8, 2024, the Court stayed discovery pending resolution of Defendants’ motion to dismiss, Dkt. No. 21, and the motion is now fully briefed, Dkt. Nos. 22 (“Opp.”), 23 (“Rep.”).

DISCUSSION L LEGAL STANDARD To survive a motion to dismiss under Rule 12(b)(6), a complaint must plead “enough facts to state a claim to relief that is plausible on its face.” Bell Atl. Corp. v. Twombly, 550 U.S. 544, 570 (2007).* A claim is facially plausible “when the plaintiff pleads factual content that allows the court to draw the reasonable inference that the defendant is liable for the misconduct alleged.” Ashcroft v. Iqbal, 556 U.S. 662, 678 (2009). A complaint is properly dismissed where, as a matter of law, “the allegations in a complaint, however true, could not raise a claim of entitlement to relief.” Twombly, 550 U.S. at 558. The Court must assume all well-pled facts to be true, “drawing all reasonable inferences in favor of the plaintiff.” Koch v. Christie’s Int’] PLC, 699 F.3d 141, 145 (2d Cir. 2012); see also A.I. Trade Fin., Inc. v. Petra Bank, 989 F.2d 76, 79-80 (2d Cir. 1993) (“[A]Il allegations are construed in the light most favorable to the plaintiff and doubts are resolved in the plaintiff's favor, notwithstanding a controverting presentation by the moving party.”). However, the Court need not accept conclusory assertions. Whiteside v. Hover-Davis, Inc., 995 F.3d 315, 321 (2d Cir. 2021). On a Rule 12(b)(6) motion, a court “may review only a narrow universe of materials.” Goel v. Bunge, Ltd., 820 F.3d 554, 559 (2d Cir. 2016). That universe includes “the facts alleged in the complaint, documents attached to the complaint as exhibits, and documents incorporated by reference in the complaint.” United States ex rel. Foreman v. AECOM, 19 F Ath 85, 106 (2d Cir. 2021). Here, the Court may consider the Trust Agreement and bank statements attached as

3 Unless otherwise indicated, case quotations omit all internal citations, quotation marks, footnotes and omissions, and adopt alterations.

Exhibits 1 through 6 to the Complaint, because they are incorporated by reference in and integral to the Complaint. See Dkt. Nos. 1-1 to 1-6. II. PLAINTIFFS’ CLAIM IS TIME-BARRED A. Florida Law Applies to Plaintiffs’ Claim Defendants claim that Florida law applies to the parties’ dispute and that, under Florida law, Plaintiffs’ claim is time-barred.

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John Francis Calicchio and Vincent Colabella, as Cotrustees of the Thomas A. Calicchio 2010 Trust Under Agreement Dated May 1, 2020 v. Lisa M. Jackson, Tate Jackson, and Phillip J. Michaels, as the Executors of the Estate of John Calicchio, Deceased, Counsel Stack Legal Research, https://law.counselstack.com/opinion/john-francis-calicchio-and-vincent-colabella-as-cotrustees-of-the-thomas-nysd-2026.