Meet Cynthia


Cynthia Leppert is a trusted strategic advisor and advocate for businesses and individuals. She formed the Law Office of Cynthia Leppert, LLC in 2021, after thirty years as a principal owner of one of Baltimore’s most preeminent mid-sized law firms. Her clients – both businesses and individuals, including fellow lawyers – come to her knowing that she will devote her full energies to their matters. Further, her familiarity and comfort with both day-to-day business issues and the courts, as well as issues that confront clients who are in the public eye, add a perspective that can be invaluable when navigating sensitive matters.

As an advisor, Cynthia provides Outside General Counsel services to start-ups and growing businesses with respect to everything from formation, governance, and funding to day-to-day matters such as contracts and employment matters. She also advises on ventures, strategic partnerships, and crisis and risk management. Cynthia has particularized experience with compliance, HIPAA, IP, and other issues confronting healthcare and technology companies. Her years of significant success as a business litigator enable her to counsel corporate clients and draft agreements so as to minimize business risk. Her natural affinity for business and financial concepts allows her to understand the practical and contextual impact of legal decisions. Additionally, her experience presenting cases to judges and juries has fine-tuned her ability to effectively persuade in negotiations.

As a litigator, Cynthia handles court cases and arbitrations, but is also keenly aware of the cost of litigation, and thus works closely with clients to negotiate favorable resolutions (both in structured mediations and more informally) where appropriate. A strong advocate, she has significant experience handling both small and high-stakes cases spanning a wide variety of substantive areas, including contracts, real estate, trademark infringement, unfair competition, partnership disputes, employment, covenants not to compete, defamation, and commercial disputes.  

Separate from her services as an advisor and litigator, Cynthia is also a trained mediator, who can be retained as a neutral to assist individuals and/or businesses resolve disputes without the costs of litigation. She brings to her mediation practice the perspective and broad substantive knowledge developed over forty years as a practicing lawyer and litigator.

Listed in Best Lawyers in America and SuperLawyers, Cynthia is a past President of the Bar Association of Baltimore City, the Baltimore Bar Foundation, and the Women’s Bar Association of Maryland. She currently Chairs the Baltimore County Ethics Commission. The Daily Record, Maryland’s business and legal newspaper, has named her to its list of Maryland’s Top 100 Women and honored her with its Leadership in Law Award. Recognized by her peers for her litigation successes, Cynthia is a Fellow in the invitation-only honor society, Litigation Counsel of America, whose membership is open to only one-half of one percent of U.S. lawyers. She is also a well-respected bankruptcy litigator and was included in LawDragon’s inaugural list of 500 Leading Bankruptcy and Restructuring Lawyers.

Cynthia graduated from Johns Hopkins University (B.A., Economics), completed a one-year Regent’s Fellowship in the UCLA Graduate School in Economics, and earned her J.D. from the UCLA Law School where she was Comments Editor of the UCLA Law Review.

Awards & Recognitions

  • Best Lawyers in America (2012-present)
  • Maryland Super Lawyers (2007-present)
  • Margaret Brent – Juanita Jackson Mitchell Award, Bar Association of Baltimore City (2023) – Woman Lawyer Trailblazer Award
  • LawDragon, 500 Leading U.S. Bankruptcy and Restructuring Lawyers (2020 – Inaugural List).
  • The Daily Record, “Leadership In Law” Award (2005).
  • The Daily Record, recognized as one of “Maryland’s Top 100 Women” (2006, 2008, 2011)
  • The Daily Record,  inducted into the “Circle of Excellence” (2011)
  • Law and Politics, “Top 50 Women Lawyers in Maryland” (2008)
  • Baltimore County Commission for Women, “Baltimore County Woman of The Year” (2008)
  • Baltimore Smart CEO Magazine, “Smart Lawyer” (2004, 2005)
  • Martindale-Hubbell AV Rating (1994-present)
  • American Bar Foundation, Fellow (2008-present)
  • Maryland Bar Foundation, Fellow (2005-present)
  • Baltimore Bar Foundation, Fellow (2007-present)
  • Litigation Counsel of America, a National Trial Lawyer Honorary Society, Charter Fellow (2006-present)
  • Women’s Bar Association of Maryland, “President’s Award” (2004, 2006, 2007, 2015)

Leadership Positions in Professional Organizations

  • Bar Association of Baltimore City
    • President (2013-2014)
    • Other Officer Positions (President-Elect, Vice President, Treasurer and Secretary)  (2009-2013)
    • Chair, Small Firm Committee (2022-present)
    • Chair, Membership Committee (2006-2009)
    • Chair, Continuing Legal Education (CLE) Committee (2005-2006)
    • Executive Council (2005-2015)
    • Advisor to Personnel Committee (2022-2023)
    • Ethics Committee (2005-2007, 2012-2020)
    • Long Range Planning Committee (2017-2020)
    • Bench Bar Committee (2012-2020)
  • Baltimore Bar Foundation
    • President (2011-2012)
    • Other Officer Positions (Treasurer and Secretary)(2009-2011)
    • Trustee (2009-present)
  • Baltimore County Bar Association
    • Professionalism Committee (2019-present)
  • Maryland State Bar Association
    • Executive Committee (2020-2021)
    • Board of Governors (2014-2016, 2019-2021, 2023-present)
    • Co-Chair, Professional Development Project and Summit (2022-present)
    • Ethics Committee (2014-present)
    • Planning Committee (2016-2018)
    • Faculty, Professionalism Course required for all new Admittees to the Maryland Bar (2002-2011)
  • Women’s Bar Association of Maryland
    • President (2007-2008)
    • Other Officer Positions (President-Elect, Vice President, Treasurer and Secretary)  (2004-2007)
    • Co-Chair of Advisory Committee to Board
    • Chair or Co-Chair, Judicial Selections Committee (2000-2004)
    • Chair, Rita C. Davidson Award Dinner, which honored U.S. Supreme Court Justice Sandra Day O’Connor at the historic conclusion of her tenure on the Court and was attended by over 500 lawyers and judges (2005)
    • Task Force on Judicial Selections Policies and Procedures (2008-2009)
    • Executive Committee (2000-2016)
    • President, Baltimore Chapter (1999-2000)
  • National Conference of Women’s Bar Associations
    • Board of Directors (2007-2012)
  • Maryland Women’s Bar Foundation
    • Board of Directors (2007-present)
    • Chair, “Finding Justice” Project (2014-present)
    • Development Committee, “Finding Justice” Project (2008-2013)
  • Attorney Grievance Commission
    • Peer Review Committee (2001-present)
    • Inquiry Committee (1998-2001)
  • Maryland Institute for The Continuing Professional Education of Lawyers (MICPEL)
    • Board of Trustees (2004-2012)

Community Involvement

  • Baltimore County Ethics Commission
    • Chair (2020-present) and Commissioner (2019-present), appointed by the County Executive of Baltimore County, Maryland and confirmed by Baltimore County Council
  • Baltimore County Blue Ribbon Commission on Ethics and Accountability (2022-2023), appointed by the County Executive of Baltimore County, Maryland
  • Baltimore County Work Group on Ethics and Accountability (2018-19), appointed by the County Executive of Baltimore County
  • Baltimore County Diversity, Inclusion and Equity Community Advisory Council
  • Maryland Commission for Women
    • Commissioner, appointed by Governor of Maryland (2002-2007)
  • Pro Bono Resource Center of Maryland
    • Co-Chair, 25th Anniversary Gala (2015)
  • Finance Committees for various Maryland, Baltimore County and Baltimore City elected officials (2009-present)
  • National Association of Women Business Owners, Baltimore Chapter
    • Secretary and Director (2005-2007)
    • Education Chair and Director (2007-2009)
  • Wakefield Improvement Association
    • President (2008-2010)
    • Board of Directors (2003-2006, 2008-2012)


  • University of California, Los Angeles (UCLA) School of Law (J.D.)
    • Comments Editor, UCLA Law Review
  • UCLA Graduate School (Regents’ Fellow, Economics)
  • The Johns Hopkins University (B.A., Political Economy, with Honors)

Professional Background

  • Staff Attorney, Federal Trade Commission (1983-1986)
  • Partner, formerly Associate, Frank, Bernstein Conaway & Goldman (1986-1992)
  • Equity Principal, Neuberger, Quinn, Gielen, Rubin & Gibber P.A. (1996-2021); Nonequity Principal (1993-1995); Attorney (1992-1993)
  • Administrative Committee (2016-2021)
  • Compensation Committee (2017-2020)

Representative Matters

General Business Representation and Outside General Counsel Services (as Sole or Lead Counsel)

  • Outside General Counsel for highly successful, growing, cutting-edge company in the IT/Health Care industry, beginning with start-up and continuing through its growth into a thriving, prosperous mid-life company and acquisition by a publicly traded company, providing advice to management on a daily basis regarding a full array of business issues.
  • Outside General Counsel for growing health care start-up, beginning with ideation and formation and continuing through all growth phases, including structuring of entity and affiliates; counseling on governance, seed and Series A capital raises, employment matters, and equity plans; drafting employment and restrictive covenants agreements, custom customer and vendor agreements, business associate agreements and data use agreements; advising regarding compliance and privacy matters; drafting privacy policies; and advising on board matters.
  • Outside General Counsel for several health care providers or provider groups, including drafting and negotiating vendor agreements, counseling on employment matters, and advising on compliance and privacy-related matters.
  • Outside General Counsel for web-based health care provider, drafting terms of use and privacy policies, and handling other privacy and compliance matters.
  • Represented several technology firms in their separate acquisitions by other technology firms, including strategic structuring of acquisitions, and drafting and negotiation of deal documents.
  • Represented a title company and its owners in company’s acquisition by Fortune 500 company, including strategic negotiation of structure of acquisition and deal documents.
  • Outside Lead General Counsel to a defense manufacturing contractor located in Puerto Rico, providing advice to owners on full array of business issues, successfully taking Puerto Rico federal bar exam at client’s request (receiving highest score in the Commonwealth) to more fully serve the client.
  • Provided issue-specific advice to closely held businesses in diverse industries regarding a variety of strategic and contractual matters.
  • Represented numerous businesses or individuals in negotiation of employment agreements or severance packages, including with respect to non-competes, other covenants and buyouts of restricted stock.
  • Represented numerous businesses or individuals in varied industries in contractual negotiations to protect intellectual property and developments.

Real Estate Litigation (as Sole or Lead Counsel)

  • Represented the seller in the trial of a real estate broker’s claim for a $1.2 million commission on the sale of a $19 million warehouse, and in the subsequent appeal. Judgment was entered in favor of the seller and the Fourth Circuit affirmed the trial court’s judgment.
  • Represented the owner of undeveloped land valued at $2 million in a boundary dispute, obtaining an agreement that successfully resolved the dispute before trial.
  • Successfully represented numerous purchasers of residential real estate with respect to claims against brokers, sellers and/or home inspectors regarding undisclosed defects.

Trademark/Copyright and Business Tort (as Sole or Lead Counsel)

  • Obtained a jury verdict in favor of an apparel manufacturer in a lawsuit under the Federal Arbitration Act to compel arbitration of a multi-million dollar trademark dispute. At the subsequent arbitration, won a decision from the arbitrator that the manufacturer owned the subject trademarks.
  • Represented a wine distributor in a trademark action filed by wine manufacturer, obtaining in mediation a settlement permitting the distributor to continue to market under the subject trademark.
  • Represented a sausage manufacturer in a trademark action against a distributor, obtaining a settlement pursuant to which the distributor would no longer be permitted to market its own sausage under the subject trademark.
  • Represented several businesses or employees with respect to claims asserted by or against them for misappropriating employees, client lists or trade secrets, obtaining favorable judgments or settlements in each case.
  • Represented publishers in various copyright actions brought by alleged owners of copyrights, obtaining favorable settlements in each case. 

Contract and Commercial Disputes (as Sole or Lead Counsel)

  • Represented manufacturer in the trial of a supplier’s claim for amounts allegedly due under a purchasing contract. Obtained judgment in favor of manufacturer after presenting expert testimony by the former chief documents examiner for the U.S. Secret Service establishing the authenticity of a second contract which precluded the supplier’s claim, and which had been alleged to be a forgery.
  • In arbitration, successfully defended signatory to a letter of intent pertaining to a contemplated joint venture against a claim that the letter was not binding. Obtained a ruling from the arbitrator that the letter of intent was binding.
  • Represented a defense contractor in a dispute with supplier, obtaining a $1 million judgment.
  • Represented guarantors of promissory notes in numerous lawsuits brought to enforce guarantees and obtained favorable resolution, often by identifying deficiencies in the guarantee or failures by the lender to comply with requirements under the guarantee or promissory note. 
  • Represented indemnitors under commercial agreements in several lawsuits brought to enforce indemnities, and obtained dismissals or settlements for a small fraction of the claims.
  • Represented defendants in numerous confessed judgment actions and obtained orders vacating the confessed judgments and ultimately favorable resolutions of the lawsuits.

 Employment Disputes (as Sole or Lead Counsel)

  • Represented numerous employers or employees in lawsuits arising out of employment contracts, including claims for severance or enforcement of covenants not to compete. 
  • In a dispute concerning an executive’s compliance with provisions of employment contract, obtained a preliminary injunction against the honoring of a letter of credit securing the executive’s “golden parachute” severance payment.
  • Represented a corporation in the arbitration of a $1.2 million severance claim brought by its former president, and uncovered evidence of the president’s fraud in procuring his employment. The arbitrator ruled in favor of the client corporation on the former president’s claim and required the former president to pay damages to the corporation.
  • Represented employers or employees in Maryland Wage Act claims arising from employer’s non-payment of severance payment upon termination of employment. 
  • Obtained trial verdict against former employee’s claim of severance and for damages under the Maryland Wage Act.
  • Represented numerous employers or employees in disputes or litigation regarding whether the employee had been terminated without cause and thus were entitled to severance payments, obtaining favorable outcome for client.
  • Represented numerous individuals or employers in negotiation of employment agreements or severance packages, including with respect to non-competes, other covenants, equity awards, or buyouts of restricted stock.
  • Represented numerous individuals or employers in negotiations of contractual provisions to protect intellectual property and developments.

Bankruptcy Litigation (as Sole or Lead Counsel)

  • Represented bankruptcy trustee in a suit against a corporation’s former law firm based upon allegations that the law firm had an undisclosed personal interest conflict at the time it was representing the corporation. Supervised audit of law firm’s invoices. Case settled for a $1 million reduction in legal fees.
  • Represented bankruptcy trustee in a trial of the trustee’s claim against a life insurance company for repayment of an unauthorized post-petition transfer. Obtained judgment in trustee’s favor from the Bankruptcy Court, and obtained appellate decisions from the District Court and Fourth Circuit affirming the Bankruptcy Court’s judgment.
  • Managed litigation of 400 preference lawsuits brought on behalf of the trustee of a bankrupt corporation. Coordinated a team of accounting and business valuation experts and, based upon a detailed forensic analysis of the corporation’s financial records and assets, worked with the experts in developing evidence that the corporation was insolvent on pivotal dates. Personally handled mediations resulting in recoveries exceeding $5 million.
  • Represented bankruptcy trustee in resolving approximately 1,000 claims by landlords for rejection damages. Developed and utilized a method for evaluating and defending the claims which dramatically reduced the value of these claims at very low cost and risk to the bankruptcy estate. As a result, was invited to present a paper on the methodology for litigating landlord claims at ABA Annual Meeting. 
  • Represented bankruptcy trustee in litigation that successfully established ownership of estate property, the title to which had been obscured by fraud. 
  • Represented a bankruptcy trustee in litigation against debtor who had fraudulently transferred assets to a related corporation and obtained favorable settlement.
  • Represented numerous defendants in preference/ avoidance lawsuits brought by bankruptcy trustees, obtaining settlements for small fractions of the claims.

Insurance Coverage and Claims Disputes (as Sole or Lead Counsel)

  • Represented a real estate developer with respect to a coverage claim against an insurance carrier and a negligence claim against a title examiner, obtaining a favorable settlement in mediation.

Family Law (as Sole or Lead Counsel)

  • Represented individuals in divorce proceedings, including high-conflict break-ups and visitation disputes.
  • Represented, on several occasions, individuals in breakups of same-sex partnerships.

Personal Injury (as Sole or Lead Counsel)

  • Represented plaintiff in auto tort case, obtaining settlement of $600,000 for pain and permanent damage to arm and shoulder mobility.
  • Represented plaintiff in auto tort case, obtaining settlement of $200,000 prior to mediation for injuries to back and residual pain even after surgery.
  • Represented plaintiff in auto tort case, obtaining policy limits of $50,000 in pre-litigation negotiation despite absence of permanency.

Bar Admissions

  • Maryland
  • U.S. Supreme Court
  • U.S. Court of Appeals for the 4th Circuit
  • U.S. District Court for the District of Maryland
  • U.S. District Court for the District of Puerto Rico
  • U.S. District Court for the Northern District of Texas
  • U.S. Court of Federal Claims