Cultivating The Next Generation of Advocates
Careers
Massey & Gail LLP is a litigation boutique with offices in Chicago and Washington, D.C. Since our founding in 2008 by Jonathan Massey and Leonard Gail, we have expanded by hiring talented lawyers who handle complex matters for sophisticated clients. We are a firm of predominantly generalist litigators who represent clients across a broad range of industries, including banking, retail, pharmaceuticals, transportation, gaming, and technology. Jonathan and Lenny have cultivated a collaborative culture grounded in mutual respect, open communication, and commitment to clients. Our goal is to provide legal services at the highest level of quality, sophistication, and professionalism while continuing to grow thoughtfully.
The Work
Our attorneys handle complex litigation and appeals in courts across the country on behalf of sophisticated clients facing significant business, financial, and reputational stakes. We staff matters with lean, highly experienced teams that work closely with clients at every stage of a dispute. Associates work substantively on some of our most significant and high-profile matters. Recent associate experience has included briefing and arguing appeals, taking and defending depositions, arguing substantive motions, drafting key pleadings, examining witnesses at trial, and interacting directly with clients and opposing counsel.
The Standard
We look for lawyers with strong factual and legal analytical abilities, excellent writing and communication skills, sound judgment, a determined work ethic, and a genuine commitment to practicing law at a high level. Our work demands intellectual rigor, professionalism, responsiveness, and the ability to work collaboratively in fast-moving and high-stakes matters.
Professional Development
As a boutique, we aim to provide associates with meaningful opportunities for professional growth and hands-on experience across all stages of litigation. Associates are given substantial responsibility early in their careers and are encouraged to develop into well-rounded litigators capable of managing engagements and handling all aspects of client counseling and dispute resolution. Our lean staffing model allows associates to work closely with senior lawyers and clients while gaining meaningful courtroom and case-management experience.
Structure and Benefits
Massey & Gail provides a comprehensive compensation and benefits package. In line with our philosophy of zealously supporting our clients while also encouraging a healthy life-work balance, our billable hours requirement is 1,800 hours per year, and we expect all of our employees to work in the office a minimum of four days per week. We also offer work schedules with reduced hours and more flexibility in certain circumstances.
Open Positions
We are seeking associate attorneys, particularly candidates with two to four years of experience. We also welcome applications from judicial law clerks. If interested in joining us, please send a resume, cover letter, law school transcript, and writing sample to .