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 pride ourselves on being predominantly generalists who practice in many substantive areas of the law and for clients operating in a broad range of business sectors—from banking, retail, and pharmaceuticals to transportation, gaming, and technology. Our deep bench of seasoned attorneys handles cases and arguments on nimble teams and works hand-in-glove with our clients. Jonathan and Lenny have cultivated a firm with a collaborative culture based on mutual respect, open communication, and client commitment. Ultimately, our goal is to consistently provide legal services to all of our clients at the highest level of quality, sophistication, and professionalism. And we are growing.

As a boutique, we aim to provide associates terrific opportunities for professional growth and to participate in the full spectrum of litigation activities at all stages of a matter. For example, recently, associates have taken and defended depositions, argued substantive motions in court, drafted important pleadings, and examined witnesses at trial. Our associates routinely interact directly with clients and opposing counsel, and they work substantively on some the firm’s most significant and high-profile cases. Though specific assignments depend upon our clients’ needs and the firm’s docket, we hope over time to develop our associates into well-rounded professionals who are fully capable of running engagements and handling all aspects of client counseling and litigation.

Massey & Gail provides a comprehensive compensation and benefits package. In line with the firm’s 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 three days per week. We also offer work schedules with reduced hours and more flexibility in certain circumstances.

We are looking to expand our ranks of associate attorneys, especially those with two to four years of professional experience. We also welcome applications from judicial law clerks. Candidates should have strong factual and legal analytical abilities, excellent communication and writing skills, a determined work ethic, and passion for practicing law.

We invite candidates to contact us directly. If interested in joining our firm, please send a resume, cover letter, law school transcript, and writing sample directly to