In Parkoff v Rieger & Fried, LLP 2025 NY Slip Op 04914 Decided on September 10, 2025 Appellate Division, Second Department Plaintiff had an otherwise good claim against the attorneys, and, after a while, asked to amend the complaint to add the otherwise good claim. Supreme Court said no. The AD reversed.

“In September 2021, the plaintiff commenced this action against the defendants, his former attorneys, to recover damages for legal malpractice arising out of the defendants’ representation of the plaintiff in a matrimonial action against his former spouse. In June 2023, the plaintiff moved pursuant to CPLR 3025(b) for leave to amend the complaint to add a fifth cause of action.

The proposed amended complaint alleged that during the pendency of the matrimonial action, the plaintiff paid income taxes on the exercise of stock options and restricted stock units issued to him by his employer. The proposed amended complaint further alleged that, while the matrimonial court had determined that the plaintiff was entitled to recover from his former spouse 50% of the taxes paid in the form of a credit on the distributive award, the defendants failed to make a claim for that credit on behalf of the plaintiff. Finally, the proposed amended complaint alleged that, but for this failure, the plaintiff would have been credited $292,760.63 against amounts that he owed his former spouse.

The defendants opposed the motion, arguing, inter alia, that the plaintiff unduly delayed in moving for leave to amend the complaint and, in any event, the proposed amendment was palpably insufficient and patently devoid of merit because the judgment of divorce in the plaintiff’s matrimonial action did, in fact, permit the plaintiff the credit he sought. The Supreme Court denied the plaintiff’s motion. The plaintiff appeals.

A party may amend his or her pleading “at any time by leave of court or by stipulation of all parties” (CPLR 3025[b]). “Generally, leave to amend a pleading shall be freely given absent prejudice or surprise resulting directly from the delay unless the proposed amendment is palpably [*2]insufficient or patently devoid of merit” (Spina v Browning Hotel Props., LLC, 230 AD3d 613, 613 [alteration and internal quotation marks omitted]; see Bisono v Mist Enters., Inc., 231 AD3d 134, 140; Kyung Hee Moon v Owadeyah, 223 AD3d 793, 795). Here, the Supreme Court improvidently exercised its discretion in denying the plaintiff’s motion pursuant to CPLR 3025(b) for leave to amend the complaint. The proposed amendment was not palpably insufficient or patently devoid of merit because, while the judgment of divorce in the plaintiff’s matrimonial action provided that the plaintiff was entitled to the subject credit, the judgment of divorce required that “[t]he parties shall exchange proof of said expenses within 30 days.” The proposed amendment sufficiently alleged that the defendants negligently failed to make a claim for the credit on the plaintiff’s behalf in the manner envisioned by the judgment of divorce.

Moreover, while the defendants contend that the plaintiff unduly delayed in moving for leave to amend the complaint, “[i]n the absence of prejudice or surprise resulting directly from the delay in seeking leave, applications to amend or supplement a pleading are to be freely granted unless the proposed amendment is palpably insufficient or patently devoid of merit” (Itzkowitz v Ginsburg, 186 AD3d 579, 581 [internal quotation marks omitted]; see CPLR 3025[b]). The burden of demonstrating prejudice or surprise falls upon the party opposing the motion (see U.S. Bank Trust, N.A. v Carter, 164 AD3d 539, 541-542; Deutsche Bank Trust Co. Ams. v Cox, 110 AD3d 760, 762). Here, the defendants did not allege prejudice (see Itzkowitz v Ginsburg, 186 AD3d at 579; Guangzhou Sanhua Plastic Co., Ltd. v Fine Line Prods. Corp., 165 AD3d 899).

Accordingly, the plaintiff’s motion for leave to amend the complaint should have been granted (see Itzkowitz v Ginsburg, 186 AD3d at 579).”

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Andrew Lavoott Bluestone

Andrew Lavoott Bluestone has been an attorney for 40 years, with a career that spans criminal prosecution, civil litigation and appellate litigation. Mr. Bluestone became an Assistant District Attorney in Kings County in 1978, entered private practice in 1984 and in 1989 opened…

Andrew Lavoott Bluestone has been an attorney for 40 years, with a career that spans criminal prosecution, civil litigation and appellate litigation. Mr. Bluestone became an Assistant District Attorney in Kings County in 1978, entered private practice in 1984 and in 1989 opened his private law office and took his first legal malpractice case.

Since 1989, Bluestone has become a leader in the New York Plaintiff’s Legal Malpractice bar, handling a wide array of plaintiff’s legal malpractice cases arising from catastrophic personal injury, contracts, patents, commercial litigation, securities, matrimonial and custody issues, medical malpractice, insurance, product liability, real estate, landlord-tenant, foreclosures and has defended attorneys in a limited number of legal malpractice cases.

Bluestone also took an academic role in field, publishing the New York Attorney Malpractice Report from 2002-2004.  He started the “New York Attorney Malpractice Blog” in 2004, where he has published more than 4500 entries.

Mr. Bluestone has written 38 scholarly peer-reviewed articles concerning legal malpractice, many in the Outside Counsel column of the New York Law Journal. He has appeared as an Expert witness in multiple legal malpractice litigations.

Mr. Bluestone is an adjunct professor of law at St. John’s University College of Law, teaching Legal Malpractice.  Mr. Bluestone has argued legal malpractice cases in the Second Circuit, in the New York State Court of Appeals, each of the four New York Appellate Divisions, in all four of  the U.S. District Courts of New York and in Supreme Courts all over the state.  He has also been admitted pro haec vice in the states of Connecticut, New Jersey and Florida and was formally admitted to the US District Court of Connecticut and to its Bankruptcy Court all for legal malpractice matters. He has been retained by U.S. Trustees in legal malpractice cases from Bankruptcy Courts, and has represented municipalities, insurance companies, hedge funds, communications companies and international manufacturing firms. Mr. Bluestone regularly lectures in CLEs on legal malpractice.

Based upon his professional experience Bluestone was named a Diplomate and was Board Certified by the American Board of Professional Liability Attorneys in 2008 in Legal Malpractice. He remains Board Certified.  He was admitted to The Best Lawyers in America from 2012-2019.  He has been featured in Who’s Who in Law since 1993.

In the last years, Mr. Bluestone has been featured for two particularly noteworthy legal malpractice cases.  The first was a settlement of an $11.9 million dollar default legal malpractice case of Yeo v. Kasowitz, Benson, Torres & Friedman which was reported in the NYLJ on August 15, 2016. Most recently, Mr. Bluestone obtained a rare plaintiff’s verdict in a legal malpractice case on behalf of the City of White Plains v. Joseph Maria, reported in the NYLJ on February 14, 2017. It was the sole legal malpractice jury verdict in the State of New York for 2017.

Bluestone has been at the forefront of the development of legal malpractice principles and has contributed case law decisions, writing and lecturing which have been recognized by his peers.  He is regularly mentioned in academic writing, and his past cases are often cited in current legal malpractice decisions. He is recognized for his ample writings on Judiciary Law § 487, a 850 year old statute deriving from England which relates to attorney deceit.