University of Virginia School of Law, J.D., 1986

  • Robert E. Goldstein Award

Dartmouth College, B.A., 1981

  • Sigurd Larmon Scholar
  • Rufus Choate Scholar
  • Longwood Cup
  • Brooks Cup
  • Chase Peace Prize
  • Ranked first nationally for intercollegiate debate, 1980-1981


  • French
Photo of Cy  Smith

Cy Smith


Cy Smith’s work as a trial lawyer often puts him in the spotlight, most recently for his representation of retired NFL players who received multiple concussions during their careers, only to be shortchanged by the league’s pension plan. The New York Times recently covered Cy’s representation of former players in a class action suit against the league, in addition to covering prior cases involving individual players injured while playing for the Washington Redskins and New York Titans (now the Jets).

Cy’s work for football retirees began in 2005 when he helped the family of the late Pittsburgh Steelers great Mike Webster win a multimillion-dollar judgment in retroactive benefits and other relief from the Bert Bell/Pete Rozelle NFL Player Retirement Plan. The case was the first-ever win against the NFL pension plans, and paved the way for today’s public, litigation, and legislative scrutiny of the benefits available to retired players. Cy testified before the U.S. House Judiciary Committee and has appeared on HBO and ESPN to discuss the NFL’s pension plan.

With more than a quarter century’s experience as a trial lawyer, Cy has represented plaintiffs and defendants in complex securities, class action, sports law, products liability, professional malpractice, and business tort cases. His wide variety of plaintiffs’ cases includes medical, legal, and accounting malpractice claims; shareholder derivative suits and securities matters; and defamation claims, resulting in a number of multimillion-dollar verdicts and settlements. He has also represented defendants in a similar range of complex civil litigation matters.

No stranger to the challenges of high-stakes—and high-profile—cases, Cy represented the son of real estate mogul and corporate raider Victor Posner in a multimillion-dollar settlement in one of the largest will contests in U.S. history. More recently, Cy represented an accountant in the Manila office of a global construction firm, who was kidnapped and tortured after the employer refused either to pay his ransom or permit his family to do so.

Cy has also represented clients who are witnesses, targets, and defendants in federal investigations and administrative proceedings concerning insider trading, money laundering, false statements to the government, insurance fraud, and other

  • Represented a class of nursing home residents challenging Maryland’s refusal to provide deductions for Medicaid recipients’ pre-eligibility medical expenses for long-term care. The settlement—one of the two largest settlements or judgments ever against the state of Maryland—will pay up to $16 million for the benefit of the class and bring the state into compliance with federal law.
  • Represents a class of consumer borrowers alleging that their title insurance transactions were steered by kickbacks paid by a national title insurer in violation of the federal RESPA statute. After prevailing in the U.S. Court of Appeals for the Ninth Circuit, the U.S. Supreme Court granted certiorari to review the case, then—on the last day of the October 2011 term, seven months after argument—dismissed the writ as improvidently granted, leaving the U.S. Court of Appeals for the Ninth Circuit’s decision intact.
  • Represented the estate of ex-Pittsburgh Steelers great Mike Webster in the first-ever win against the National Football League’s (NFL’s) pension plan, proving that Mike had been crippled by multiple concussions from his NFL career. His win led to testimony before Congress and paved the way for today’s media, public, legislative and litigation scrutiny of pro football’s concussion crisis.
  • Represented an accountant who was kidnapped, tortured, and held for ransom in the Philippines; his employer had refused both to pay the ransom demanded and to tell his family so that they could secure his release. The case settled on confidential terms after we won back-to-back victories in the U.S. Court of Appeals for the District of Columbia Circuit—and unearthed a video of our client’s imprisonment and torture.
  • Served as counsel for the shareholder plaintiff in a case against the directors, senior officers, and accountants of a bank, resulting in a $10 million-plus settlement because of the bank's enormous losses from unsecured loans to an unscrupulous mobile-home retailer.
  • Represented plaintiffs who won enforcement of a highly favorable pension plan amendment, defeating claims that it was the product of a federal labor racketeering conspiracy and resulting in one of the largest ERISA judgments ever in the U.S. Court of Appeals for the Fourth Circuit.


Mentioned & Quoted



Bar Admissions

Court Admissions

Professional Affiliations

  • Member and President (2006-2007), Board of Governors, Federal Bar Association, Maryland Chapter
  • Member, Criminal Justice Act Panel, U.S. District Court, District of Maryland, 1991—2008

Community Involvement

  • President (2011—present) and Member (2005—present), Board of Trustees, Beth Am Synagogue
  • Member and Vice Chair, Board of Directors, Baltimore Urban Debate League, 2004—2011
  • Member and Chairman (2003-2004), Lawyers’ Campaign for the College Bound Foundation
  • Chair, Friends of City College Speech and Debate, 2008—present