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Mary-Caitlin Ray

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Areas of Focus

Overview

Mary-Caitlin is a versatile aviation attorney whose practice uniquely combines sophisticated M&A and transactional experience with deep Federal Aviation Administration (FAA) and Department of Transportation (DOT) regulatory experience, giving clients a rare, integrated perspective that is essential for navigating one of the world's most heavily regulated industries. A former attorney in the FAA's Office of the Chief Counsel, she delivers practical, business-savvy counsel to aircraft owners, operators, lessors, manufacturers, supply chain stakeholders, and investors across the full spectrum of aviation transactions and regulatory challenges. Her clients rely on her to move quickly, manage risk, and capitalize on opportunity—whether they are structuring a transformative acquisition, entering a new aviation market, or resolving a complex regulatory matter.

Mary-Caitlin's practice is rooted in business aviation, where she advises clients on the acquisition and sale of business aircraft—including complex cross-border transactions—and on the full range of operating structures, including dry leasing, timesharing, and fractional ownership agreements. She has represented numerous individuals and corporations in the acquisition of fractional interests in aircraft and counsels Fortune 500 flight departments and high-net-worth individuals on regulatory matters ranging from permitted compensation and pilot licensing to responses to FAA investigations and audits. As the industry evolves, she helps her business aviation clients anticipate and navigate the regulatory and technological changes reshaping the sector.

That forward-looking perspective extends naturally into the emerging aviation technologies space, where Mary-Caitlin is a recognized advisor to UAS (drone) and eVTOL manufacturers, operators, and their investors on FAA and DOT regulatory compliance, the business impact of new and evolving rulemakings, remote identification requirements, and the development of internal aviation policies and best practices. Her government experience at the FAA gives her clients a distinct advantage—she understands how regulators think and how to engage constructively with the agency to achieve practical, business-driven outcomes. She has represented a major drone manufacturer in navigating U.S. aviation regulatory matters and new rulemakings and regularly advises the investors and stakeholders backing next-generation aviation businesses on the full regulatory implications of their positions.

Whether the matter involves a transformative M&A transaction, a novel regulatory question, or a time-sensitive operational issue, Mary-Caitlin brings the aviation industry knowledge, cross-practice collaboration, and client-first pragmatism that today's transportation clients demand.

Career & Education

    • Department of Veterans Affairs
      Attorney-Advisor, 2013–2014
    • Federal Aviation Administration
      Attorney, Office of the Chief Counsel, 2014–2018
    • Department of Veterans Affairs
      Attorney-Advisor, 2013–2014
    • Federal Aviation Administration
      Attorney, Office of the Chief Counsel, 2014–2018

    • Washington and Lee University School of Law, J.D., 2012
    • Washington and Lee University, B.A., cum laude, 2009
    • Washington and Lee University School of Law, J.D., 2012
    • Washington and Lee University, B.A., cum laude, 2009

    • District of Columbia
    • Massachusetts
    • New York
    • Supreme Court of the United States
    • District of Columbia
    • Massachusetts
    • New York
    • Supreme Court of the United States

  • Professional Activities and Memberships

    • Membership Chair and Governing Committee American Bar Association Forum on Air and Space Law
    • Regulatory Issues Advisory Counsel, National Business Aviation Association (“NBAA”)
    • International Aviation Women’s Association, Member
    • ISTAT, Member

    Professional Activities and Memberships

    • Membership Chair and Governing Committee American Bar Association Forum on Air and Space Law
    • Regulatory Issues Advisory Counsel, National Business Aviation Association (“NBAA”)
    • International Aviation Women’s Association, Member
    • ISTAT, Member

    • Mandarin
    • Mandarin

Mary-Caitlin's Insights

Client Alert | 3 min read | 07.02.26

Prohibiting Adversarial Patents Act of 2026 (H.R. 9142): What the Drone Industry Needs to Know

On June 4, 2026, Rep. Scott Fitzgerald (R-WI-5) introduced a bill that would limit the ability of people and entities seen as threats to U.S. national security to obtain and enforce patents. If enacted, the Prohibiting Adversarial Patents Act of 2026 (H.R. 9142) would leverage use of patent law as a national security tool, with consequences for companies operating in technology-intensive sectors, including drones, telecommunications, semiconductors, artificial intelligence, and advanced manufacturing. The proposed legislation, currently under review by the U.S. House Judiciary Committee, is particularly focused on persons and entities with connections to the People’s Republic of China....

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Representative Matters

Transactional

  •  Represented a major automobile manufacturer in the formation of a manufacturing joint venture with an eVTOL manufacturer, providing aviation regulatory due diligence and counsel on the aviation-specific implications of the transaction and of the go-forward manufacturing business.
  • Represented a large multinational manufacturer in the spin-off of its aircraft cabin business, advising on the regulatory and transactional aspects of the separation.
  •  Represented a lessor in standing up aircraft leasing platform, including the acquisition and leasing of a business jet fleet and a fleet of over 50 trainer aircraft, including negotiation of lease documentation and regulatory structuring.
  • Represented numerous individuals and corporations in the acquisition of fractional interests in aircraft, advising on operational structures, operating agreements, and regulatory compliance.
  • Represented numerous private equity funds in conducting transactional due diligence and providing regulatory counsel related to the acquisition and sale of aviation-related businesses, including MROs, manufacturers, aircraft owners and operators, and UAS and eVTOL manufacturers and operators.
  • Represented buyers and sellers in numerous aircraft purchase and sale transactions, including cross-border transactions requiring the export or import of aircraft.
  • Advised on the aircraft and flight department implications of numerous corporate restructurings and spin-offs, including aircraft operating, registration, and financing matters.

Emerging Technologies (UAS and EVTOL)

  •  Represented a major drone manufacturer in U.S. aviation regulatory matters, including compliance with FAA rulemakings and the development of internal aviation policies and best practices.
  •  Advised UAS manufacturers on compliance with remote identification regulations, including the development of technical and operational compliance strategies.
  •  Drafted internal UAS use and remote identification policies for commercial UAS operators and manufacturers, including Fortune 500 companies.
  • Advised small UAS operators on FAA operating and registration rules, including counsel on new and upcoming FAA rulemakings affecting sUAS operations.
  • Conducted investor-led reviews of the certification progress of an eVTOL manufacturer to support additional infusions of capital.

FAA Regulatory and Compliance

  • Counseled numerous FAA certificate holders, including PMA holders and Part 145 Repair Station Certificate holders, on responses to whistleblower complaints, FAA investigations, audits, and Letters of Investigation related to quality escapes and incidents.
  • Advised Fortune 500 flight departments and high-net-worth individuals on complex regulatory issues related to permitted compensation, pilot licensing, and operating structures including dry leasing and timesharing arrangements.
  • Advised clients on negotiating lease documents and operating agreements related to Part 91 operations.
  • Drafted manned and unmanned internal aircraft use policies for corporate flight departments and commercial UAS operators.

Mary-Caitlin's Insights

Client Alert | 3 min read | 07.02.26

Prohibiting Adversarial Patents Act of 2026 (H.R. 9142): What the Drone Industry Needs to Know

On June 4, 2026, Rep. Scott Fitzgerald (R-WI-5) introduced a bill that would limit the ability of people and entities seen as threats to U.S. national security to obtain and enforce patents. If enacted, the Prohibiting Adversarial Patents Act of 2026 (H.R. 9142) would leverage use of patent law as a national security tool, with consequences for companies operating in technology-intensive sectors, including drones, telecommunications, semiconductors, artificial intelligence, and advanced manufacturing. The proposed legislation, currently under review by the U.S. House Judiciary Committee, is particularly focused on persons and entities with connections to the People’s Republic of China....

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Recognition

  • Chambers USA
    • Transportation: Aviation: Regulatory - Nationwide, 2025–2026
    • Transportation: Aviation: Transactional - Nationwide, 2026
  • Lexology Index: Transport, 2023-2026
  • National Business Aviation Association (NBAA): Business Aviation Top 40 Under 40 Award, 2023

Mary-Caitlin's Insights

Client Alert | 3 min read | 07.02.26

Prohibiting Adversarial Patents Act of 2026 (H.R. 9142): What the Drone Industry Needs to Know

On June 4, 2026, Rep. Scott Fitzgerald (R-WI-5) introduced a bill that would limit the ability of people and entities seen as threats to U.S. national security to obtain and enforce patents. If enacted, the Prohibiting Adversarial Patents Act of 2026 (H.R. 9142) would leverage use of patent law as a national security tool, with consequences for companies operating in technology-intensive sectors, including drones, telecommunications, semiconductors, artificial intelligence, and advanced manufacturing. The proposed legislation, currently under review by the U.S. House Judiciary Committee, is particularly focused on persons and entities with connections to the People’s Republic of China....

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Insights

Client Alert | 3 min read | 07.02.26

Prohibiting Adversarial Patents Act of 2026 (H.R. 9142): What the Drone Industry Needs to Know

Firm News | 7 min read | 06.04.26

Crowell & Moring Secures Top Rankings in Chambers USA 2026

Client Alert | 4 min read | 05.14.26

No-Fly Zones for Drones: FAA Proposes New Rules Over Critical Infrastructure

Client Alert | 4 min read | 01.29.26

FAA Invites Fresh Input on Expansive Drone Rule

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Practices

Industries

Mary-Caitlin's Insights

Client Alert | 3 min read | 07.02.26

Prohibiting Adversarial Patents Act of 2026 (H.R. 9142): What the Drone Industry Needs to Know

On June 4, 2026, Rep. Scott Fitzgerald (R-WI-5) introduced a bill that would limit the ability of people and entities seen as threats to U.S. national security to obtain and enforce patents. If enacted, the Prohibiting Adversarial Patents Act of 2026 (H.R. 9142) would leverage use of patent law as a national security tool, with consequences for companies operating in technology-intensive sectors, including drones, telecommunications, semiconductors, artificial intelligence, and advanced manufacturing. The proposed legislation, currently under review by the U.S. House Judiciary Committee, is particularly focused on persons and entities with connections to the People’s Republic of China....

View All Insights