Dave Flanagan

Dave Flanagan is the founding attorney of Flanagan & Associates, a results-driven law firm based in Weymouth, Massachusetts. With over 22 years of legal experience, Dave is known for his fearless litigation style, meticulous preparation, and client-first approach. He has successfully represented thousands of individuals throughout Quincy and the South Shore in both criminal defense and personal injury matters. Whether negotiating favorable resolutions or taking cases to trial, Dave is committed to delivering effective, trial-ready legal representation at every stage.

Investigative Background

Dave's path to the courtroom began in the field of private investigation, where he spent nearly a decade developing specialized skills that continue to set him apart as a lawyer. In 1994, he began working as a private investigator with the Claims Bureau, where he directed and executed surveillance operations on behalf of major insurance providers. His work uncovered fraudulent insurance activity and gave him unique insight into the tactics used by insurers and law enforcement alike.

In 1999, Dave joined Liberty Mutual Insurance as a claims adjuster, further deepening his understanding of claim valuation and internal insurance operations. He later founded and operated his own investigative agency, where he continued to support insurance investigations while refining the skills—fact analysis, evidence evaluation, and strategic planning—that now drive his courtroom success.

Legal Career

Motivated to do more for individuals than the insurance system allowed, Dave pursued a law degree and earned his Juris Doctor from New England School of Law in 2003. While in law school, he served on the staff of the Journal of Criminal and Civil Confinement, an academic publication focused on real-world impacts of the justice system. This experience helped shape his grounded understanding of how legal decisions affect people’s lives beyond the courtroom.

Upon graduation, Dave immediately began practicing law with a focus on criminal defense and personal injury. Drawing on his investigative and insurance background, he brings a comprehensive, strategic approach to every case—anticipating opposition tactics and preparing thoroughly for any scenario.

Trial Advocacy & Practice Areas

Dave has earned a strong reputation for his trial skills, particularly in cases involving:

• Criminal Defense — including OUI/DUI, drug offenses, violent crimes, and theft
• Personal Injury Litigation — such as car accidents, premises liability, and workplace injury

Known for his courtroom presence and refusal to back down when justice is at stake, Dave does not shy away from taking a case to trial when that’s what’s required to achieve the best outcome. Clients benefit from his confidence, preparation, and command of both the facts and the law.

Philosophy & Local Commitment

A Quincy native, Dave remains deeply committed to serving the community that shaped him. He understands the stress and uncertainty that legal matters can create, and he prioritizes clear communication, honest advice, and strategic action. Dave approaches each case with a fresh perspective—developing customized trial strategies that reflect the facts, the client's goals, and the potential outcomes.

Whether helping someone fight a criminal charge, recover damages from an injury, or protect their rights in court, Dave ensures his clients never face the system alone.

Education & Bar Admissions

• J.D., New England School of Law, 2003
• Staff Member, Journal of Criminal and Civil Confinement
• Licensed to Practice in:
  • All Massachusetts State Courts (District, Superior, Appeals, and Supreme Judicial Court)
  • United States District Court for the District of Massachusetts

Testimonials

• Client in Norwood, MA - "Thanks, Dave, you made a difficult process for me easy. I will tell all that I know the wonderful job you did."
• Client in Stoughton, MA - "Attorney Flanagan handled my case and got me a settlement that was much more than I thought I would get. He explained exactly how the insurance company works and he delivered results."
• Client in Dedham, MA - "I have dealt with many attorneys in my lifetime and no attorney was better prepared than Attorney Flanagan. He went out of his way to help me."