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Matthew Flanagan

Co-Chair, Disciplinary Board Representation Practice Group

Portrait of Matthew Flanagan

Matt is a highly skilled litigator with over 30 years of trial and appellate experience and serves as Co-Chair of the firm's Disciplinary Board Representation Practice Group. His practice is concentrated on the defense of lawyers against malpractice actions, Judiciary Law 487 claims and grievances. He also defends other professionals and handles general litigation matters on behalf of corporate clients. He has successfully tried cases in New York City and its surrounding counties and has secured dozens of victories in attorney liability cases in New York State’s appellate courts.

With a career-long focus on professional liability litigation, Matt lectures throughout the state on legal malpractice prevention and defense, ethics and professional responsibility. His articles relating to attorney ethics have been cited in the authoritative codification of the laws of New York, as well as New York’s leading treatise on the Rules of Professional Conduct.

Among his numerous professional memberships, he is the past President of the Theodore Roosevelt American Inn of Court and is a member of the New York State Bar Association's Law Practice Management and Insurance Committees. He is a longtime member of the Nassau County Bar Association and served as Chair of the Association’s Ethics Committee from 2019 to 2022. He is also a longtime member of the American Bar Association.

Matt has been recognized annually as a New York Metro Area Super Lawyer for over a decade and is rated AV Preeminent™ by Martindale-Hubbell, the highest peer-review ranking for an attorney's professional and ethical competence. A graduate of St. John's University School of Law and Fordham University, he is admitted to practice before the courts of the State of New York, the United States District Courts for the Southern and Eastern Districts of New York and the United States Court of Appeals for the Second Circuit.

    • St. John's University School of Law (J.D., 1992)
    • Fordham University (B.A., 1989)
    • New York, 1993
    • U.S. District Court Eastern District of New York, 1993
    • U.S. District Court Southern District of New York, 1993
    • U.S. Court of Appeals 2nd Circuit, 1996
    • AV® Preeminent™ by Martindale-Hubbell®
    • New York Metro Area Super Lawyer (2012-2026)
    • American Bar Association (2007-Present)
    • Nassau County Bar Association (1999-present); Ethics Committee (2011-present); Ethics Committee Chairman (2019-2022)
    • New York State Bar Association (1999-present); Law Practice Management & Insurance Committees (2011-present)
    • St. John’s University Alumni Association, Nassau Chapter (2000-present); President (2017-2020)
    • Theodore Roosevelt American Inn of Court, (2011-present); President (October 2023-present)
  • Trends In Claims, Marshall Dennehey Client Presentation, May 5, 2026

    The Art of Mediation, Marshall Dennehey Client Presentation, May 5, 2026

    Attorney Discipline, Theodore Roosevelt American Inn of Court (with program chairs Hon. Randall Eng, Appellate Division, Second Department (ret.), and Hon. Helen Voutsinas, Appellate Division, Second Department), November 15, 2023

    Risk Management and the Rules of Professional Conduct, Nassau County Bar Association, May 12, 2022

    Cybersecurity: Are You and Your Firm Compliant: A Checklist for Lawyers, Joint Presentation of Nassau County Women’s Bar Association and Nassau County Bar Association Ethics Committee, March 3, 2020

    Navigating Malpractice and Ethical Concerns for Trusts and Estates Attorneys, St. John’s University School of Law Continuing Legal Education Weekend, February 8, 2020

    Legal Malpractice: Elements & How to Avoid It, Suffolk Academy of Law, December 12, 2019

    Legal Malpractice: Reducing Your Risk and Strengthening Your Defense, St. John’s University School of Law Spring Continuing Legal Education Weekend, February 10, 2018

    Lawyers’ Ethics: Escrow Accounts (with Hon. Leonard Austin, Appellate Division, Second Department), Theodore Roosevelt American Inn of Court, December 12, 2017
    Judicial Ethics, What’s a Judge to Do? (with Hon. Vito DeStefano and Hon. Randy Sue Marber, Supreme Court, Nassau County), Theodore Roosevelt American Inn of Court, April 27, 2017

    Legal Malpractice: Professional Liability Claims, Litigation Strategies and Attorney Discipline Procedures, New York State Bar Association, Melville, New York, March 31, 2017

    Attorney Ethics: A Discussion of the New Statewide Procedures for Attorney Discipline Matters (with Abraham Krieger, Chairman of Grievance Committee for 10th Judicial District), St. John’s University School of Law Continuing Legal Education Weekend, February 25, 2017

    Legal Malpractice Update, Nassau County Bar Association, February 1, 2017

    • “Escrow Cleanup: Taking Care of the Money Left Behind,” NYSBA Journal, Vol. 90, No. 8, New York State Bar Association, October 2018
    • “On Ethics: Agreements Not To Grieve – Are They Ethical?” – Nassau Lawyer, November 1, 2017 
    • “On Ethics: Addressing Claims Against A Client's Settlement Funds,” Nassau Lawyer, March 1, 2017
    • “Bowing Out Ethically: Ending the Attorney-Client Relationship Before the Matter is Completed,” NYSBA Journal, Vol. 88, No. 7, New York State Bar Association, September 2016
    • "Follow the Money - Escrow Accounts: The Dangers of Excessive Delegation and Deference," NYSBA Journal, Vol. 87, No. 5, New York State Bar Association, June 2015

Results

Summary Judgment Secured for Law Firm

We secured summary judgment for a law firm by successfully arguing that its role in implementing and overseeing a client’s anti-money laundering policies did not encompass the accounting functions the accounting firm had agreed to perform, and that there was no evidence the law firm acted negligently. The underlying malpractice claim was brought by a check cashing company against its accountants, alleging that the accounting firm failed to detect thefts committed by one of the company’s employees. The accounting firm, in turn, filed a third-party contribution claim against the law firm, contending that the firm should have detected the employee’s thefts through its work overseeing the company’s anti-money laundering policies. The Court rejected the accounting firm’s arguments, granted our motion for summary judgment, and dismissed the contribution claim.

Dismissal Secured in New York Legal Malpractice Matter

We secured a decision granting our motion to dismiss an attorney malpractice matter in Orange County, NY. The plaintiff and daughter of the co-defendants sued her parents and our client for breach of contract, breach of fiduciary duty denominated as promissory estoppel, and constructive trust and sought damages of $800,000. The co-defendants allegedly purchased a property for the plaintiff to live and work in and agreed to deed the property to the plaintiff once she paid the mortgage in full. Our client created a family trust naming the plaintiff as trustee, in which the property would be transferred to the plaintiff following the death of both parents. However, following a family dispute, the co-defendants replaced the plaintiff as trustee with our client. Upon the request of the co-defendants and in accordance with the terms of the trust, our client transferred the house to another beneficiary. We filed a motion to dismiss on all counts which the court granted in full.

Thought Leadership

Legal Updates for Lawyers' Professional Liability

Courts in New York Continue to Crack Down on Attorneys’ Faulty Reliance on Generative Artificial Intelligence

July 29, 2026

The latest instance occurred in Landberg v. City of New York, 2026 NY Slip Op 03935, 2026 LX 36495 (2d Dept., June 23, 2026), which was a fairly simple trip and fall case. The plaintiff tripped and fell on a loose brick on a sidewalk and brought an action against the City of New York and the abutting landlord, both of which were awarded summary judgment. The Appellate Division, Second Department, affirmed the grant of summary judgment in a relatively short decision issued in early June.  The court spent far more time later in the month addressing the contents of the brief submitted on behalf of the plaintiff and the conduct of plaintiff’s attorney. In a lengthy decision, the court dissected the plaintiff’s brief, finding that it cited and/or quoted from three cases which did not exist, and then misrepresented the holdings of cases which actually did exist.  One of the fictious quotes purported to be from the court of appeals, but was “directly contrary to what the court of appeals has actually said.” After being confronted with the non-existent cases at the oral argument, the plaintiff’s attorney was offered an opportunity to take a 15-minute recess to come up with an explanation of where the nonexistent cases came from, but he declined the opportunity and said that he had “found them either on Westlaw or Lexis or in a book, a previous case, or another brief.” The court concluded that the attorney was not being candid, and that he should have said (as he later admitted) “that the cases were hallucinated by artificial intelligence.” The court imposed a monetary sanction of $8,000 on the attorney, but the court did not stop there. Although the handling attorney’s actions were contrary to the policies of the law firm he worked for, the firm was sanctioned, too (for $2,500). The attorneys for the defendants, while not sanctioned, were chastised for not alerting the court to the AI hallucinations in plaintiff’s brief.  The court wrote: “Although the attorneys for the owner and the City, who are officers of the court, submitted respondents’ briefs, neither of them alerted this Court about the fabricated citations, fabricated quotations, misstatements of law, and misrepresentations regarding the holdings of real cases contained in the plaintiff’s brief.”   Not surprisingly, the sanction exceeded the sanction which the same court had assessed a few weeks earlier against a pro se litigant. In Matter of Julien v. Arthur, 2026 NY Slip Op 03308, 2026 LX 287806  (2d Dep.t, May 27, 2026), the Second Department sanctioned a pro se litigant in the amount of $250 for his reliance on generative AI. The pro se litigant cited only one nonexistent case, but the court ruled that that was sufficient to warrant the imposition of a sanction. The Julien court noted that the pro se litigant (a father in a custody dispute) acknowledged responsibility for his conduct and that it only occurred once, which undoubtedly factored into the lower monetary sanction. The following month, in distinguishing the much lower sanction awarded in Julien, the Landberg court said: “This case is obviously much more egregious in that the person who filed the subject brief is a trained attorney with access to legal research materials, including Westlaw, and who is bound by the Rules of Professional Conduct.” Attorneys practicing in the Second Department can expect a sanction greater than $250 for even a single AI hallucination or fabricated citation in a brief. The court made it clear in Landberg that attorneys are on notice of the unreliability of generative AI: “stories about the unreliability of GenAI in performing legal work, leading to fictitious citations, misrepresentations of the law, and sanctions, have been widespread in the media for years.”  The court also made it clear that attorneys are expected to alert the court to the AI hallucinations and fabricated cases and quotations in their adversary’s briefs.  The foregoing cases coincide with the New York State Unified Court System’s adoption of a new rule, Part 161, regulating the use of AI. The new rule provides that attorneys cannot be prohibited from using artificial intelligence tools in preparing papers submitted to a court, but the tools must be used “in accordance with the duties and responsibilities that apply to individuals who submit papers to a court.” The rule goes on to suggest that individual judges should adopt a Part Rule which provides: “Every attorney or party who uses an artificial intelligence (AI) tool in preparing any paper submitted to this court is expected to understand that tool's capabilities and limitations. Attorneys and parties need to be aware that AI tools, among other risks and limitations, can generate fabricated information or fictitious citations to authority (commonly known as hallucinations)… Accordingly, any attorney or party who uses an artificial intelligence tool, as defined in 22 NYCRR 161.2(a), in preparing any paper, as defined in 22 NYCRR 161.2(b), filed in or submitted to this court or served on another party in a case before this court is required to carefully review the paper and independently ensure that it contains no fabricated or fictitious cases, statutes, or other material.” Attorneys are on notice of the pitfalls of blind reliance on generative AI and can expect to be sanctioned if they mis-cite or misquote cases in submissions which are prepared with the assistance of AI tools.    

Legal Updates for Lawyers' Professional Liability

California Supreme Court Rejects Automatic Expungement of Attorney Disciplinary Records

January 1, 2026

Last year, we reported on a California State Bar initiative to expunge attorney discipline records, other than disbarment, after eight years. See Legal Updates for Lawyers’ Professional Liability – February 2025. The proposed change was intended to lessen the impact of what was perceived as racial disparities in attorney discipline in California. A 2019 State Bar-commissioned study had found that Black male attorneys in California were more than three times as likely to be placed on probation than white male attorneys. This past October, the California Supreme Court rejected the expungement proposal, without any explanation. The court may have been persuaded by opponents of the measure, many of whom felt that the public is entitled to complete transparency when hiring an attorney. The court may have also been influenced by more recent studies which showed that the racial disparities highlighted in the 2019 study were already narrowing. A study released by the California State Bar in May of 2025 found that while some racial gaps remained, “the discipline system is trending in the right direction.” Whether relied on by the California Supreme Court or not, the report from the 2025 study has some interesting findings which could benefit all attorneys faced with disciplinary complaints. The report suggested that sending letters to encourage attorneys who are subject to disciplinary proceedings to retain counsel may have helped narrow the racial disparities found in the 2019 study. Any attorney facing a disciplinary complaint is well-advised to consult an attorney who is experienced in handing such complaints. Many attorneys are not aware that their lawyers’ professional liability policy likely includes supplemental coverage to pay attorney fees incurred in responding to grievances. The carrier can also help find an attorney to help defend against the grievance should the responding attorney need one. The California Supreme Court’s rejection of the expungement proposal opens the door to the expanded use of the less controversial (and, perhaps, more effective) methods highlighted in the report from the 2025 study, including sending letters to attorneys subject to disciplinary complaints. In addition to encouraging attorneys to retain counsel, the letters could also advise them of the supplemental coverage available under their LPL policies. Legal Update for Lawyers’ Professional Liability – January 2026 is prepared by Marshall Dennehey to provide information on recent legal developments of interest to our readers. This publication is not intended to provide legal advice for a specific situation or to create an attorney-client relationship. We would be pleased to provide such legal assistance as you require on these and other subjects when called upon. ATTORNEY ADVERTISING pursuant to New York RPC 7.1 Copyright © 2026 Marshall Dennehey, all rights reserved. No part of this publication may be reprinted without the express written permission of our firm. For reprints or inquiries, or if you wish to be removed from this mailing list, contact MEDeSatnick@MDWCG.com. 

Firm Highlights

Thought Leadership

Pennsylvania Supreme Court to Review Whether Legal Malpractice Claims May Be Recast as Breach of Contract Claims

The Pennsylvania Supreme Court recently granted allowance of appeal to consider whether a plaintiff may pursue a breach of contract claim against an attorney based on allegations that the attorney failed to provide competent legal services. The issue is significant in professional liability litigation because it concerns whether a plaintiff may avoid the statute of limitations applicable to professional negligence claims by characterizing the alleged misconduct as a breach of contract. Antoine Poteat retained attorneys Gary Asteak and Nino V. Tinari to represent him in a criminal matter. After his conviction was subsequently overturned through a Post Conviction Relief Act proceeding, Poteat filed suit against his former attorneys alleging that they breached their retainer agreements by failing to provide competent legal services. The attorneys argued that the claims sounded in professional negligence, rather than breach of contract, and were therefore time-barred. The trial court dismissed Poteat’s complaint, but the Superior Court, sitting en banc, reversed. The Superior Court held that the gist-of-the-action doctrine did not bar Poteat’s breach of contract claim because the alleged failure to provide competent legal services could constitute a breach of the parties’ agreement. The Court further held that a legal-services agreement contains an implied duty requiring an attorney to provide competent legal services, even where the agreement does not contain an express provision requiring such services. The Pennsylvania Supreme Court granted review in July 2026 and will consider whether the Superior Court’s decision conflicts with Pennsylvania precedent distinguishing contract and tort claims, including Bruno v. Erie Insurance Co. The Supreme Court will also address whether a plaintiff may maintain a breach of contract claim based on an implied duty to provide competent legal services without identifying a specific contractual provision that was breached. The Supreme Court’s decision could have significant implications for professional liability litigation in Pennsylvania, particularly where plaintiffs seek to characterize claims arising from alleged professional negligence as contractual claims.

Thought Leadership

The Search-Incident-to-Arrest Doctrine Does Not License Strip Searches

In Beatty v. Gardner, No. 25-2860 (3d Cir. Sept. 16, 2026), Kyle Beatty sued police officers Clinton Gardner and Calvin Irvin under 42 U.S.C. § 1983 after they stopped, arrested, and searched him three times during a drug investigation in Williamsport, Pennsylvania. The officers initially smelled marijuana coming from the car in which Beatty was sitting and observed marijuana residue, giving them probable cause to arrest him. Beatty consented to the first pat-down, and the second search was conducted incident to his lawful arrest; neither search uncovered weapons or contraband. The officers then transported Beatty to the police station solely to strip-search him, but the strip search also revealed nothing. The District Court granted the officers summary judgment, concluding that the initial stop, arrest, and first two searches were reasonable and that qualified immunity protected the officers from liability for the strip search. The Third Circuit affirmed, but held that the strip search itself violated the Fourth Amendment. The court concluded that the search-incident-to-arrest doctrine does not automatically permit officers to strip-search an arrestee outside the jail or prison setting. Because strip searches are highly intrusive and the traditional justifications for searches incident to arrest (officer safety and preservation of evidence) did not justify the search of Beatty, the officers generally needed either the arrestee’s consent, exigent circumstances, or a warrant supported by probable cause to believe that a search beneath the clothing would reveal weapons, contraband, or evidence. Here, the officers had none of those justifications. Nevertheless, the court held that qualified immunity barred damages liability because, at the time of the search, the right against a warrantless strip search of an arrestee outside the institutional setting was not clearly established by Supreme Court or Third Circuit precedent. The court likewise upheld qualified immunity on Beatty’s First Amendment retaliation claim and affirmed summary judgment for the officers.

Thought Leadership

Two Tracks, No Preclusion: Ohio Supreme Court Preserves Separate Damages Claims After Chapter 2506 Appeals

The Supreme Court of Ohio has clarified that an administrative appeal under Ohio Revised Code Chapter 2506 does not bar a separate action for damages and declaratory relief that could not have been pursued in the administrative appeal. The Ohio Supreme Court considered Sheetz, Inc. v. Centerville (2026-Ohio-3531) as a result of a certified question from the Southern District of Ohio. The question was whether Sheetz, the gas station/convenience store brand, was barred from seeking damages in a separate action since damages were not sought in their administrative appeal. Ultimately, the Ohio Supreme Court ruled that res judicata does not bar a separate action for damages after ruling on an administrative appeal because R.C. Chapter 2506 is limited to judicial review and cannot grant affirmative relief. The case arose after Centerville’s city council rejected a site plan proposed by Sheetz, Inc. that had received unanimous approval from the City’s planning commission. Sheetz filed an administrative appeal pursuant to R.C. 2506 in the Montgomery County Court of Common Pleas, and two months later filed a complaint for damages and declaratory relief under 42 USC § 1983 as a takings action with the city, city council, and other objectors as improper takings and a violation of due process, as well as interference with business and contractual relationship. The city and city council removed the § 1983 action for damages to federal court. Montgomery County Court of Common Pleas reversed the city council’s denial, and allowed the Sheetz project to move forward. Upon that ruling, the federal court issued a show-cause order questioning whether the § 1983 action was barred by the doctrine of res judicata via claim preclusion (which includes all theories of recovery).  Sheetz argued that Ohio courts of common pleas do not have authority to award damages or declaratory relief as party of the R.C. Ch. 2506 appeal, therefore res judicata could not be triggered to apply to the § 1983 action. Additionally, Sheetz moved to certify the issue to the Ohio Supreme Court, citing differing results between the second and sixth districts on this same issue. Centerville approached the question, not from a claim preclusion standpoint, but from the holding in Grava v. Parkman, Twp which states that a final judgment rendered on the merits bars all subsequent action based on the same transaction or occurrence.  In yet another approach, an objector argued that claim preclusion was satisfied because Sheetz could have raised its damages claims in the administrative appeal – Sheetz disagrees. In their analysis, the Supreme Court of Ohio broke down the elements of a claim preclusion analysis: 1) a prior final, valid decision on the merits by a court of competent jurisdiction; (2) a second action involving the same parties, or their privies, as the first; (3) a second action raising claims that were or could have been litigated in the first action; and (4) a second action arising out of the transaction or occurrence that was the subject matter of the previous action. The Court held that R.C. Ch. 2506 does not permit a party to argue damages as R.C. Ch. 2506 limits the common pleas jurisdiction as if it were sitting on appeal, and therefore can only affirm, reverse, vacate, or modify the appealed order, or can remand the case to the administrative body. Further, the Court held that Grava’s conclusion that a final judgment precludes additional litigation for different relief is inapplicable under this fact pattern because it was meant only to apply to those matters in which the plaintiff brings the exact same case twice, but for new relief. The Court found Grava was inapplicable because Sheetz could have requested damages or declaratory relief in the R.C. 2506 appeal. Therefore, Grava would be nothing more than dicta if it even did apply. Going further, the Ohio Supreme Court disavowed Sixth Circuit precedent which, in reliance on Grava and other district court decisions, permitted an owner to seeking relief under 42 U.S.C. § 1983 alongside an administrative appeal. See Moore v Hiram Twp., 988 F.3d 353 (6th Cir.2021). The Ohio Supreme Court found that the Sixth Circuit had disregarded a critical decision in Community Concerned Citizens, Inc. v. Union Twp. Bd. of Zoning Appeals, 1993-Ohio-115, which clearly held that a R.C. Ch. 2506 appeal cannot be combined with a complaint seeking other claims for relief. Id. at ¶ 11. To that end, the Ohio Supreme Court has determined that the decisions Moore relied on (outside of Grava) are no longer good law, and that Moore was wrongly decided. The decision draws a clear procedural boundary: Chapter 2506 provides judicial review of an administrative decision, not a forum for independent claims seeking affirmative relief. Although Grava may place claims arising from a single transaction within the potential scope of claim preclusion, those claims are not barred unless the complete claim-preclusion test is satisfied. Because Sheetz could not have pursued damages or declaratory relief in its Chapter 2506 appeal, the separate action was not precluded. The remaining question for practitioners looking to apply or defend against this exception is when does the statute of limitations begin to run on damages and declaratory relief claims related to an administrative decision on appeal? A takings action in federal court has a 2-year statute of limitations, or as a state claim, 4 years (like the other tortious claims raised therein). Correlating this case with others, an administrative appeal will not likely toll the statute of limitations on claims based on a final decision by a municipal authority. Therefore, practitioners should look for these cases to be brought simultaneously.