What Sets Us Apart


Our law firm is not a pyramid.  We’re a boutique with a deep bench of experienced lawyers who have handled dozens of mediations, arbitrations, and trials, argued in every federal circuit and the U.S. Supreme Court, participated in countless regulatory proceedings, and advised our clients on innumerable strategic matters.


Our clients get more partner time and attention because our senior lawyers are directly involved in the matters on which they are working.  We are more available, more responsive, and more directly accountable to our clients.


Our clients benefit from more creative thinking and less “auto-pilot.”  With more experienced lawyers on nimble teams directly engaged in our matters, we provide innovative solutions and strategic short-cuts that resolve disputes more quickly and more affordably.

Diversity and inclusion are core values at Massey & Gail because we recognize them as a source of our strength. During the past three years, three-quarters of our full-time attorney hires have been diverse. We believe that developing and maintaining diverse talent is fundamental to our success as a law firm.  It allows our professionals to achieve their full potential and is essential to delivering high-quality legal services to our clients.

We take active steps to achieve our diversity and inclusion goals.  This extends to attorney recruiting, professional development, and promotion.  We actively recruit female, minority, and LGBTQ lawyers, through both search firms and our attorneys’ professional networks.  We are a member of the Minority Corporate Counsel Association, an organization committed to advancing the hiring, retention, and promotion of diverse lawyers in law departments and law firms through pipeline initiatives, and by providing research, best practices, professional development, and training. Additionally, one of our partners was a 2016 Leadership Council on Legal Diversity Fellow and remains involved in mentorship and advocacy with the organization.

At Massey & Gail, we feel strongly about our communities and believe we have a duty to give back and to support those who are financially unable to access counsel for their legal needs.  To that end, our lawyers frequently take on community-impacting pro bono projects, represent indigent litigants in civil rights lawsuits, and serve as directors on boards of community-based non-profits.  For example, because of the deep background of many of our attorneys in competitive debate, our firm is a longtime sponsor of a nationwide charity that promotes competitive academic debate in inner-city and financially underserved schools. This charity not only improves educational outcomes for students, but also helps diversify the legal profession, because many successful debaters enter law school after college.

In addition, we have an active pro bono practice that has included representing criminal defendants in Chicago and the Fifth Circuit, homeless veterans in Los Angeles, prison inmates in Alabama and Illinois, a low-income high school in Chicago, and educational and art non-profits.  Members of the firm are frequent pro bono volunteers, as well as instructors at Harvard Law School, the University of Maryland, the D.C. Bar Association, and other institutions. Our partners serve on charity boards including Planned Parenthood of Illinois, the National Advisory Council of the School of Communication at Northwestern University, Chicago Run, Chicago Debates, the Chicago chapter of the American Constitution Society, and boards for a public school district and a private school.

At Massey & Gail, our fee structures span the full spectrum of financial possibilities, from pure hourly arrangements to matters in which our fees are completely contingent.  Hourly structures are often the most appropriate, and we think that clients receive an exceptional value proposition given how we efficiently staff and manage our matters. But we also know that non-hourly structures can be sensible for the right type of case.  Unlike some firms that dabble on the margins with such arrangements, we have considerable experience with non-hourly arrangements. As a result, we also understand how to gauge and bear the risks associated with them.

We want to succeed in each case that we handle, so we custom-tailor our engagements after carefully evaluating the nature, magnitude, and risks of each individual matter.  Many clients seek to manage their litigation budgets with greater certainty. Our flexible approach allows us to offer predictability that hourly billing cannot provide. Please reach out to discuss the varied, creative arrangements we are willing to consider.

Recent News

  • Massey & Gail made its debut in Benchmark Litigation’s 2020 rankings of leading law firms. Read more about Benchmark’s analysis of Massey & Gail here.
  • Eli Kay-Oliphant led the team to secure a victory for firm client Southwest Airlines in the U.S. District Court for the Northern District of Illinois. The complaint, brought on behalf of a putative class of passengers with cancelled flights due to lack of deicing fluid, was dismissed with prejudice.  The Court’s decision was covered nationally.
  • In a widely covered ruling, the U.S. Court of Appeals for the Second Circuit reinstated the Firm’s lawsuit for the parents of murdered DNC staffer, Seth Rich, against Fox News.
  • Massey & Gail files complaint on behalf of Western Values Project seeking records concerning the routing of FOIA requests at the Department of Interior to political appointees.
  • Jonathan Massey secures dismissal of putative class action against JPMorgan Chase alleging “kickbacks” in mortgage insurance.
  • Matthew Collette, drawing on his extensive experience in government and regulatory matters, shares his in-depth analysis of a recent U.S. Supreme Court decision regarding FOIA and confidential disclosures to the government in an article for Law360.
  • Paul Berks wins appeal, reinstating the firm’s taxpayer case against Home Depot, as reported in the Cook Country Record.
  • Jonathan Massey and Paul Berks analyzed a recent NCAA antitrust ruling, focusing on the tension between the court’s finding of antitrust violations against the NCAA and the challenges it faces in implementing a viable and adequate remedy. The National Law Journal reported their views.