James S. O'Brien, Jr. LinkedIn

Attorney in New York, NY

James O'Brien is a seasoned litigator with experience in complex commercial litigation and arbitration, including SEC proceedings and shareholders' class actions, entertainment and intellectual property litigation, and all types of contractual disputes. James tries cases in both federal and state courts, and litigates cases across the country. In addition, James chairs the Firm's Americans With Disabilities Act practice.

James was trial counsel for client Castillo Grand LLC in a nine-week trial against Starwood Hotels' subsidiary Sheraton Operating Corp., which resulted in a judgment of $55M in Castillo Grand's favor. The substantial ruling in Castillo Grand LLC v Sheraton Operating Corp. (N.Y. Supreme Court, Westchester County) was a result of Sheraton's multiple breaches of its management contract with the owners and developers of the former St. Regis Hotel and Resorts. The parties had entered into a contract to bring New York's famed St. Regis Hotel brand to Ft. Lauderdale's Gold Coast, making it one of the first high-end, luxury hotel and condominium resorts in the beachside community at the time. At the crux of the dispute was the absence of "St. Regis-style" brand standards in the design and construction of the hotel, caused in large part by the revolving door of senior leadership within the Starwood organization. There were four St. Regis regime changes during the design and construction of the hotel and with each change Starwood leadership imposed a new direction in the design for almost every facet of the hotel. The disorganization created ever-evolving interior building specs for the St. Regis brand and a moving design and construction standard that led directly to extensive construction delays and vast cost overruns for Castillo Grand. By the time the hotel opened in 2007, it was millions of dollars over budget, two years behind schedule, and the Florida real estate market was cratering to historic lows. To read more about this case, please click here.

James was lead trial counsel in Deep Woods Holdings LLC v. Savings Deposit Insurance Fund of the Republic of Turkey, 07-CV-934 (S.D.N.Y. 2011), in which he obtained a $25 million judgment for the client after trial. The case involved the Savings Deposit Insurance Fund of the Republic of Turkey's ("SDIF") refusal to honor the terms of an option agreement concerning shares in The Park Avenue Bank (the "Bank"). Pryor Cashman asserted claims against SDIF for breach of contract for SDIF's failure to deliver the shares as required under the call option and for its intentionally preventing the occurrence of certain conditions that triggered its performance. SDIF denied the claims and asserted a counterclaim for attorneys' fees and costs against Deep Woods as the prevailing party. The Court gave no credence to SDIF's arguments and awarded James and his team a resounding victory.

James represented Integro USA, Inc., one of the largest insurance brokers in the United States, in an AAA arbitration commenced by a former senior broker seeking a bonus and additional post-termination compensation. The broker's termination agreement provided that his post-termination benefits would cease if he accepted employment with a competitor during the time that Integro was paying him. The arbitrator ruled that: (a) the termination agreement's non-compete clause was enforceable; (b) the broker had accepted employment with a competitor; and (c) Integro rightfully had ceased its post-termination payments to the broker. In addition, the arbitrator ruled that Integro was entitled to the return of the post-termination payments it had made, plus its costs and fees.

James was principally involved in Pryor Cashman's representations of the CEOs of two Fortune 500 companies in separate consolidated, multi-district, shareholder class-actions. He was also lead trial counsel in Lockheed Martin Corporation v. Spencer Trask Intellectual Capital Company, L.L.C., in which James successfully defended six scientists in New Hampshire against Lockheed Martin's charges of theft of cutting-edge photonics technology.

James successfully defended the directors of a Connecticut corporation against allegations of fraud, RICO violations, and securities law violations arising from an $80 million stock and debenture fraud that resulted in substantial prison terms for a number of defendants, including the corporation's president.

James also has experience with bankruptcy-related litigation and represents the indenture trustees of bond issues in federal bankruptcy courts around the country. James represented the indenture trustees in Delaware in In re Kaiser Aluminum Corporation, Case No. 02B-10429 (JKF), and in In re American Business Financial Services, Inc., Case No. 05-10203, one of the first sub-prime bankruptcies.

James also routinely litigates real estate-related matters and was lead counsel in a number of construction law actions arising from the construction of a union-financed hospital in New York City. James also has litigated product liability and toxic tort cases, having been lead counsel representing Boyle Drug Company in 242 DES (diethylstilbestrol) cases brought in New York County.

James graduated from Tulane University Law School, where he was Articles Editor of the Tulane Law Review, in 1986. James won the Tulane Law School Writing Competition in 1984 and the Moot Court Competition in 1986. He was a Senior fellow, Legal Research and Writing, in 1985-86. James earned a B.A. degree from the United States Merchant Marine Academy, where he graduated cum laude, in 1979.

Previous Positions

· Olwine, Connelly, Chase, O'Donnell & Weyher, Associate (1989-91)

· Burlingham, Underwood & Lord, Associate (1987-89)


· Co-Author (with S. Bell & S. Kline), The ADA and Access to Pools and Other Recreational Facilities, Bloomberg BNA Real Estate Law & Industry Report (June 2012)

Professional Affiliations

· New York State Bar Association

Other Activities

· FAA Certified Private Pilot

· U.S. Coast Guard licensed Master Mariner

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Areas of Law

  • Litigation
  • Alternative Dispute Resolution
  • Americans With Disabilities Act Defense
  • Antitrust and Trade Regulation
  • Appeals
  • Bankruptcy Court Litigation and Appeals
  • Class Action Defense
  • Complex Contract and Commercial Litigation
  • Contested Administrative Proceedings and Litigation: Banking
  • Criminal, White Collar, Administrative, Enforcement and Regulatory Defense
  • Entertainment Litigation
  • Financial Institutions Group
  • Hospitality Litigation
  • Intellectual Property, Copyright and Trademark Litigation
  • Music Litigation
  • Privacy and Defamation
  • Investment Management Group
  • Real Estate Litigation
  • Regulatory, Corporate Compliance and Internal Investigations
  • Restrictive Covenants, Trade Secrets and Duty of Loyalty
  • Securities Litigation
  • Terminations and Severance Arrangements
  • Trade Secret Litigation
  • Trusts and Estates: Litigation
  • White Collar Defense and Investigations
  • Intellectual Property
  • Copyright
  • Entertainment, Media and Communications
  • Labor and Employment
  • Bankruptcy, Reorganization and Creditors' Rights
  • Corporate Trust: Defaults and Bankruptcies
  • Corporate
  • General Business Law


Experience & Credentials



Admission Details

Admitted in 1987, New York
1987, U.S. District Courts for the Southern and Eastern Districts of New York
2012, U.S. Court of Appeals for the Second Circuit

Law School Attended

Tulane University Law School
Class of 1986

University Attended

United States Merchant Marine Academy
Class of 1979
cum laude

Contact Information






Send email to James S. O

Office Information
James S. O'Brien, Jr.
 7 Times Square,
New York, NY 10036-6569


Pryor Cashman LLP (New York, New York)

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