S. Penny Windle

S. Penny Windle

S. Penny Windle


212.701.3693 Phone vCard
212.378.2621 Fax

Cahill Gordon & Reindel LLP
80 Pine Street
New York, NY 10005-1702



  • Columbia University, A.B., 1991
  • Columbia Law School, J.D., 1997, Harlan Fiske Stone Scholar


  • New York

Penny Windle is a member of Cahill Gordon & Reindel LLP's litigation practice group and serves on its Development Committee. She has also served as Co-Administrative Partner of the firm.

Penny represents global corporations, leading banks, boards of directors, special committees and directors and officers of publicly-held companies in high-stakes commercial litigation and government investigations, with particular emphasis on complex securities, insurance and reinsurance matters.

Penny served as a lead counsel in the defense of McGraw Hill Financial, Inc. and Standard & Poor’s Financial Services, LLC in a FIRREA lawsuit brought by the United States Department of Justice and related lawsuits brought by the attorneys general of 19 states and the District of Columbia relating to the rating of residential mortgage-backed securities and collateralized debt obligations in the years preceding the financial crisis. Penny also served as a lead counsel in multiple investigations by the United States Securities and Exchange Commission and several additional state attorneys general, as well as multiple private lawsuits, in related matters.

Other clients have included Deutsche Bank, Bankers Trust Company, American International Group, Kemper Insurance Company, Global Reinsurance, ABC, The New York Times Company and many others.

Penny has a long track record of success in leading internal investigations and responding to governmental inquiries, particularly those arising from financial, accounting and insurance matters. She has represented companies and their boards in investigations and proceedings before the Securities and Exchange Commission, numerous state attorneys general, the United States Department of Justice and other state and federal regulatory entities.

Penny joined Cahill in 1997, following her tenure as a Financial Analyst with Kidder Peabody & Co., Inc. and Bear Stearns & Co. Inc., and became a partner in 2006. Penny is recognized as a New York Litigation Star and one of the "Top 250 Women in Litigation" in the United States by Benchmark Litigation, and is recommended by The Legal 500.

  • Represented McGraw Hill Financial, Inc. and Standard & Poor’s Financial Services, LLC in a FIRREA lawsuit brought by the United States Department of Justice, as well as lawsuits and investigations brought by numerous state attorneys general, the United States Securities and Exchange Commission, private litigation and other related matters.
  • Represented international insurance company in connection with various matters under investigation by the New York Attorney General and others relating to contingent commissions to insurance brokers.
  • Represented both insurance and reinsurance entities in a variety of reinsurance arbitrations and litigation.
  • Represented numerous companies in a variety of industries in defense of purported class action lawsuits and related litigation, including derivative actions.
  • Represented the Special Litigation Committee of the Board of Directors for a major retailer in connection with derivative lawsuits.
  • Represented numerous companies and boards in internal investigations arising from allegations of misconduct by current or former employees and others.
  • Represented numerous companies in disputes concerning post-closing adjustments relating to the sale of businesses or business units.
  • Represented prominent real estate investment and management partnership in arbitration proceedings and related litigation involving hotel/casinos in Las Vegas and condominium hotels in Florida.
  • Represented numerous companies in matters relating to intellectual property, including successful defense of a trademark action brought against a health supplement company and a patent infringement case brought against a biopharmaceutical company.