Gary Oberstein, former managing partner of the Boston office, currently serves as Senior Counsel in the Labor & Employment group. Gary passionately provides strategic legal advice to employers of all sizes across most industries regarding all aspects of the employment relationship and represents them in the resolution of employment-related disputes.
For nearly 30 years I have devoted my practice to assisting employers with a broad array of business and human resources issues arising out of employment. I help employers solve immediate problems practically, while providing predictive and proactive counsel and forecasting the challenges and opportunities that lay ahead. I focus on efficiently helping employers achieve their business and personnel objectives while minimizing legal exposure and business disruption.
I work strategically with employers to craft novel, pragmatic solutions to complex employee management problems. Some of my favorite work involves intricate performance and/or conduct management problems, including high stakes c-suite management issues. Clients call on me to navigate the increasingly complex world of employee leave requests and medical issues, including the intersection of the ADA with myriad other leave laws, workers compensation and disability insurance.
I focus on helping employers guard against costly wage-hour suits, such as exempt employee status, payroll practices and meal and rest period issues. I regularly head teams that conduct customized audits and also defend employers against wage-hour suits.
I have deep and wide experience with the labor and employment aspects of complex (and simple) reorganizations/restructurings and reductions in force, including significant job eliminations and international transfers. These multi-layered actions implicate dozens of statutes and often require the development of first-impression creative solutions involving the minimization of exposure to discrimination and other wrongful termination claims, compliance with WARN, the OWBPA and state laws, crafting internal and external communications approaches and preparing separation documentation.
I am watching for a new trend to develop with the plaintiff’s bar focusing on “reverse discrimination” claims (male/Caucasian) and greater scrutiny of employers’ attempts to diversify their workplaces. In addition, I expect the aging workforce trend, tied to increasing life expectancy, will result in more age and disability claims and require employers to change their thinking about traditional retirement, mentoring, and benefits.
Boston College Law School, J.D., cum laude
Vassar College, A.B., with honors
Gary was selected, through a peer-review survey, for inclusion in The Best Lawyers in America® 2022 in the field of Employment Law—Management. Gary has been listed in Best Lawyers since 2016.
Gary has been recognized for the seventh consecutive year for exceptional standing in the legal community in Chambers USA: America’s Leading Lawyers for Business 2015 for Labor & Employment (Massachusetts). He has also been recognized in Chambers in previous years.
He is also recognized as a top attorney by Super Lawyers.
Gary currently serves as executive director and chairman of the Board of Directors of Above the Clouds (ATC), and is a member of the Board of Advocates of Jewish Families & Children’s Service and the Board of Directors of IMC Club International, Inc. He also serves on the Board of Advisors for Ollie’s House (a homeless shelter for victims of domestic violence).
Gary has served on the Massachusetts Bar Association’s Labor and Employment Law Section Council, served as chairperson of the section’s Employee Rights and Responsibilities Committee, chaired the section’s monthly group discussion series, and has served as liaison of the Labor and Employment Law Section of the Boston Bar Association. He was also a member of the Massachusetts Continuing Legal Education’s Employment and Labor Law Curriculum Advisory Committee.