Jeffrey K. O'Connor

Jeff is a seasoned litigator, trial lawyer, and strategic counselor.  For over fifteen years, he has guided medical and legal professionals, businesses, municipalities, and non-profit organizations through complex civil litigation, agency proceedings, risk management challenges, and regulatory minefields.  Whether in the courtroom or the conference room, Jeff is an attentive, creative, solutions-oriented advocate who understands client needs.

Jeff returned to Cain Hibbard after twelve years as an associate and partner of a regional, Boston-based firm where the bulk of his practice was defending medical and legal malpractice cases through trial and appeal, and representing professionals in licensing and disciplinary matters.  Jeff has also defended employment discrimination claims on behalf of both secular and religious employers; litigated commercial disputes; and guided clients under investigation by state and federal agencies.  Throughout his career, Jeff has counseled health care organizations in HIPAA, Stark, and other areas of regulatory compliance.

Jeff earned his B.A from Bradford College and his J.D. from Western New England University School of Law, where he was Senior Note Editor of the Western New England Law Review, and later served on its Advisory Committee.  He enjoys running, hiking, reading, writing, and exploring the world with his spouse, Andrea, and their two children.

Jeffrey K. O’Connor, Partner

[email protected]

Pittsfield, MA

Tel (413) 443-4771
Fax (413) 443-7694
Direct Dial  (413) 629-1337



Bradford College, BA, cum laude, 2000
Western New England University School of Law, JD, cum laude, 2007


Commonwealth of Massachusetts
U.S. District Court, District of Massachusetts


Massachusetts Bar Association
Berkshire County Bar Association
Hampden County Bar Association