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Mary-Caitlin Ray

Senior Counsel | She/Her/Hers
Senior Counsel | She/Her/Hers
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VCard
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Areas of Focus

Overview

A former attorney for the Federal Aviation Administration, Mary-Caitlin represents aircraft owners, operators, and manufacturers as well as investors into aviation related businesses, advising on regulatory and transactional matters. Her clients come to her for practical and strategic advice on navigating complex aviation challenges. She has significant experience advising clients on the impacts of and solutions for emerging technologies in the aviation sector, including uncrewed aircraft systems (UAS or drones) and electric vertical takeoff and landing (eVTOL) aircraft.

Mary-Caitlin’s practice spans the crewed and uncrewed side of the aviation world.

She has advised Fortune 500 flight departments, high net worth individuals, and manufacturers and suppliers on regulatory concerns related to the operation and production of aircraft, including complex issues related to permitted compensation, pilot licensing, operating structures such as dry leasing, timesharing and fractional ownership agreements, and emergency and Letter of Investigation response related to quality escapes and incidents. She also represents clients in the acquisition and sale of business aircraft, including cross-border transactions requiring the export or import of aircraft.

Mary-Caitlin counsels drone and eVTOL manufacturers, operators, and owners on all aspects of FAA regulatory compliance, including the business impacts of the evolving global regulatory framework for emerging aviation technologies. She also advises drone manufacturers and operators developing internal aviation-related corporate policies and best practices.

Mary-Caitlin has significant experience advising investors on the regulatory implications of investment into a wide array of aviation-related businesses, including MROs, manufacturers (including eVTOL manufacturers), and businesses that own and/or operate aircraft.

Career & Education

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    • 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, B.A., cum laude, 2009
    • 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

    • 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

    • Chair, Young Lawyers Committee of the American Bar Association Forum on Air and Space Law
    • Young Lawyer Liaison to the American Bar Association Forum on Air and Space Law
    • Member, International Society of Transport Aircraft Trading
    • Member, Women in Aviation International
    • Vice Chair, ABA Section of Public Contract Law Young Lawyers Committee, 2017–2018

    Professional Activities and Memberships

    • Chair, Young Lawyers Committee of the American Bar Association Forum on Air and Space Law
    • Young Lawyer Liaison to the American Bar Association Forum on Air and Space Law
    • Member, International Society of Transport Aircraft Trading
    • Member, Women in Aviation International
    • Vice Chair, ABA Section of Public Contract Law Young Lawyers Committee, 2017–2018

    • Mandarin
    • Mandarin

Mary-Caitlin's Insights

Client Alert | 1 min read | 02.29.24

IRS to Kickoff Audit Campaign Focused on Business Aircraft Users

Last week, the IRS announced plans to begin a campaign to audit personal use of business aircraft. The audits will focus on whether large corporations, partnerships and high-and ultra-high net worth aircraft owners have properly reported their business and personal aircraft usage for tax purposes, with a particular focus on ensuring that owners are only taking deductions to which they are entitled. Given the value of an aircraft, the amount of a deduction for aircraft related expenditures on a given taxpayer’s return can be in the tens of millions of dollars, and with more than 10,000 corporate jets operating in the U.S., IRS Commissioner Daniel Werfel recognized that much is at stake with this campaign.  The audit campaign is expected to focus initially on multinational and domestic corporations and complex partnerships but is expected to expand from there....

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Representative Matters

  • Advised small UAS operators on FAA operating and registration rules, including counseling on new and upcoming FAA rulemakings affecting sUAS operations.
  • Advised UAS manufacturers on compliance with remote identification regulations.
  • Drafted internal UAS use and remote identification policies for commercial UAS operators and manufacturers.
  • Represented buyers and sellers in numerous aircraft purchase and sale transactions.
  • Advised clients on negotiated lease documents related to Part 91 operations.
  • Represented numerous private equity funds in conducting transactional due diligence and counseling related to the acquisition and sale of aviation related businesses, including Maintenance and Repair Organizations, manufacturers, aircraft owners and operators, and UAS and eVTOL manufacturers and operators.
  • Counseled numerous FAA certificate holders, including PMA and Part 145 Repair Station Certificate holders, on responses to FAA investigations and audits.

Mary-Caitlin's Insights

Client Alert | 1 min read | 02.29.24

IRS to Kickoff Audit Campaign Focused on Business Aircraft Users

Last week, the IRS announced plans to begin a campaign to audit personal use of business aircraft. The audits will focus on whether large corporations, partnerships and high-and ultra-high net worth aircraft owners have properly reported their business and personal aircraft usage for tax purposes, with a particular focus on ensuring that owners are only taking deductions to which they are entitled. Given the value of an aircraft, the amount of a deduction for aircraft related expenditures on a given taxpayer’s return can be in the tens of millions of dollars, and with more than 10,000 corporate jets operating in the U.S., IRS Commissioner Daniel Werfel recognized that much is at stake with this campaign.  The audit campaign is expected to focus initially on multinational and domestic corporations and complex partnerships but is expected to expand from there....

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Recognition

  • Who’s Who Legal (WWL): Transport, 2023, 2024, 2025
  • National Business Aviation Association (NBAA): Business Aviation Top 40 Under 40 Award, 2023

Mary-Caitlin's Insights

Client Alert | 1 min read | 02.29.24

IRS to Kickoff Audit Campaign Focused on Business Aircraft Users

Last week, the IRS announced plans to begin a campaign to audit personal use of business aircraft. The audits will focus on whether large corporations, partnerships and high-and ultra-high net worth aircraft owners have properly reported their business and personal aircraft usage for tax purposes, with a particular focus on ensuring that owners are only taking deductions to which they are entitled. Given the value of an aircraft, the amount of a deduction for aircraft related expenditures on a given taxpayer’s return can be in the tens of millions of dollars, and with more than 10,000 corporate jets operating in the U.S., IRS Commissioner Daniel Werfel recognized that much is at stake with this campaign.  The audit campaign is expected to focus initially on multinational and domestic corporations and complex partnerships but is expected to expand from there....

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Insights

Client Alert | 1 min read | 02.29.24

IRS to Kickoff Audit Campaign Focused on Business Aircraft Users

Client Alert | 2 min read | 01.10.24

New Year, Larger Penalties: What DOT Regulated Businesses Need to Know

Firm News | 2 min read | 10.16.23

NBAA Names Mary-Caitlin Ray a 2023 Business Aviation Top 40 Under 40 Recipient

Press Coverage | 10.13.23

Mary-Caitlin Ray – 2023 Business Aviation Top 40 Under 40 Award Recipient
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Practices

Industries

Mary-Caitlin's Insights

Client Alert | 1 min read | 02.29.24

IRS to Kickoff Audit Campaign Focused on Business Aircraft Users

Last week, the IRS announced plans to begin a campaign to audit personal use of business aircraft. The audits will focus on whether large corporations, partnerships and high-and ultra-high net worth aircraft owners have properly reported their business and personal aircraft usage for tax purposes, with a particular focus on ensuring that owners are only taking deductions to which they are entitled. Given the value of an aircraft, the amount of a deduction for aircraft related expenditures on a given taxpayer’s return can be in the tens of millions of dollars, and with more than 10,000 corporate jets operating in the U.S., IRS Commissioner Daniel Werfel recognized that much is at stake with this campaign.  The audit campaign is expected to focus initially on multinational and domestic corporations and complex partnerships but is expected to expand from there....

View All Insights