Robert C. Penn Jr.

+1 212 202 2649

Robert brings a strong client focus to his complex commercial litigation practice. Clients value his ability to simplify the intricacies of technical litigation and formulate strategies that help them achieve their goals.

Whether advising on a business breakup, a commercial contract matter, or an action involving confidential information, Robert is adept at navigating complex legal territory to secure optimal outcomes.

Before joining Sher Tremonte, Robert was an associate at Wollmuth Maher & Deutsch LLP, where he represented individual and institutional corporate clients in commercial litigation matters involving antitrust, securities, and business law, as well as clients in bankruptcy adversary actions and arbitration. During law school, Robert interned at the New York Attorney General’s Office in the Antitrust Bureau, assisting in investigations into anti-competitive and monopolistic practices.

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  • Representing one of two former co-principals in a business divorce involving claims and counterclaims regarding unauthorized payments and reputational damage as well as the ongoing financial and operational health of the original business.
  • In a breach of contract action, representing a corporate plaintiff seeking payment from former clients amid challenges as to the best way to reach defendants’ assets given their questionable financial health.
  • Representing a blockchain technology company and its founders in dispute with an outside investor and related action by client to recover against former senior executive for breaches of non-solicitation and confidentiality obligations.
  • On a pro bono basis, representing an individual pursuing claims against a federal agency related to an assault by prison staff.

Other notable work includes:

  • Obtained dismissal on summary judgment of all claims and won summary judgment on the clients’ counterclaim in the representation of a boutique investment bank and cable management consulting company in a breach of contract action against a national media company.
  • Prevailed on a motion to dismiss plaintiff’s employment discrimination claims in representation of a business development company.
  • Represented a medical malpractice insurance company owned by an American multinational conglomerate against claims of breach of fiduciary duty.
  • Represented holders of residential mortgage-backed securities (RMBS) in claims against trustees of RMBS trusts for breach of contractual duties.


Recognized in Best Lawyers: Ones to Watch® in America for Corporate Law (2024)



The National Black Lawyers – Top 100 Black Lawyers in New York (2021-present)

Metropolitan Black Bar Association (2016-present)

Historical Society of the New York Courts (2016-present)

New York City Bar Association (2008-present)