Bob Flynn

bioshotCA office: (619) 500-9700

MA office: (781) 239-1005

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For nearly 20 years Attorney Robert H. Flynn has provided mediation and arbitration services to  lawyers and their clients.  As a trial lawyer, Bob brings more than 40 years of experience representing insurers, self-insurers and claimants. Bob’s ADR focus is on traditional tort, professional negligence and insurance cases.

Profession: Mediator & arbitrator in the following types of cases:

  • Accidents (auto, premises, products liability, construction,  transportation)
  • Malpractice (medical and dental, nursing home, assisted living)
  • Professional negligence (legal, accounting, engineering)
  • Insurance (bad faith and coverage)
  • Error & omission cases (architects, engineers, insurance and real estate broker)
  • Real estate (buyers, sellers, agents and brokers fees)
  • Lease (commercial and residential)
  • HOA and condominium
  • Partnership and trust
  • Construction disputes (owners, generals, suppliers, subs and professionals)
  • Employment cases
  • Business, commercial and contract cases

Experience: Two decades as a neutral in mediation and arbitration! Often court appointed in Suffolk, Worcester and Middlesex Counties in Massachusetts as an arbitrator and discovery master! Formerly, on the American Arbitration Association panel.

Decades of experience preparing, trying and settling civil cases for insurers, defendants and claimants. Fifteen appellate cases before the United States Court of Appeals, 1st Circuit; the Massachusetts Supreme Judicial Court; the Massachusetts Appeals Court and the United States Supreme Court (Application for Certiorari).

Bob’s keys to guiding parties to settlement include his practical trial experience and a skill at listening and finding consensus.

  • AV rated Martindale Hubbell
  • Super Lawyer Designation 2011- 2018
  • Perfect 10 rating AVVO

Professional History: Trial lawyer representing insurers and claimants in real estate, construction, professional, employment, tort and insurance cases since 1973.

  • Coast to Coast ADR, 2014 – present, Principal
  • Flynn Law Firm, P.C., 2002 – present, Principal (MA only)
  • Fay, Flynn & Fay, P.C., 1982 – 2002, Partner
  • Hale, Sanderson, Byrnes & Morton, 1973 – 1982, Associate and Partner

Bar Admissions:  Supreme Judicial Court, Commonwealth of Massachusetts, 1973; United States District Court, Massachusetts, 1975;  United States Court of Appeals, First Circuit, 1977; United States Supreme Court, 1995.

Professional Associations: American Bar Association (past TIPS Committee Chair); Massachusetts Bar Association; Boston Bar Association; San Diego County Bar Association (Chair, Dispute Resolution Section); North County Bar Association; Formerly member of the following: Defense Research Institute (past Committee Chair); International Association of Defense Counsel; Professional Liability Underwriters Association; Massachusetts Defense Lawyers Association; Norfolk Bar Association; Metro West Bar Association; American Association for Justice; Massachusetts Academy of Trial Attorneys; and Transportation Lawyers Association.

Education: Boston College, AB, History, 1970; Boston College Law School, JD, 1973; Staff, Boston College Industrial & Commercial Law Review.

Publications, Appellate Experience and Speaking Engagements: “Essential Litigation Skills for Massachusetts Paralegals”, Institute for Paralegal Education, 2003, 2004; “The Legal Investigator as a Witness,” THE LEGAL INVESTIGATOR, August, 2000; “Organizing the Defense File,” THE PRACTICAL LITIGATOR, July, 1995; Speaker and Chair various seminars, programs and presentations at ABA Annual Meetings (TIPS), at DRI Annual Meetings and at local meetings and conferences including MATA and the Massachusetts Licensed Private Detective Association.

Community Activities:

  • Northeast Accessible Golf Association (Past Chairman, Board of Directors)
  • Host, “Talking about the Law”, weekly on WCRN, Radio 830 AM
  • Wellesley Little League Parent, Coach, Manager and President
  • Town of Wellesley, Town Meeting Member for many years; Affordable Housing Committee member; Town Finance or Advisory Committee member

For further information, see Bob’s profile featured on and

Experienced. Prompt. Effective.