Retired Judge Simons is available to handle conciliations and mediations independently, or in tandem with retired Judge Linda Fidnick.

The Hon. Richard A. Simons (Ret.) has devoted much of his career to assisting individuals navigating issues surrounding separation, divorce, guardianship, and estate administration. Prior to his appointment to the Bench in 2008, Judge Simons practiced law in Pittsfield with the firm of Simons, Smith & Gerrard where he litigated cases in all departments of the trial court and was a pioneer in introducing a mediation practice to the Berkshire County legal landscape in the early ’90s. In 1999, Massachusetts Lawyers Weekly recognized Judge Simons as one of its ten “Lawyers of the Year”.

Governor Deval Patrick appointed Simons to the Probate and Family Court, where he served for over 18 years until his retirement in August 2026. He served as First Justice of the Berkshire Division starting in 2010. In 2014, he and his Chief Probation Officer conceived of and implemented a program, “Enhancing Families Through Literature” based on a successful alternate sentencing program, “Changing Lives Through Literature.”  In 2016, the Association of Family and Conciliation Courts (AFCC) recognized the program with the Irwin Cantor Innovative Program Award for innovation in a court-connected program.

While on the bench, Judge Simons served on the Trial Court’s Committee on Changing Lives Through Literature and was active in the J2J Mentoring Program by mentoring judges and training judges to be judicial mentors. He was the chair of the Probate and Family Court’s Education Committee and was a Trustee of the Flaschner Judicial Institute. In 2024, Trial Court Chief Justice Brieger appointed Judge Simons to be the Trial Court’s designate to the Board of the Massachusetts Legal Assistance Corporation.

Throughout his legal career, Judge Simons has been a guest speaker at various professional association and MCLE events, and has many publications and reported decisions.

In the community, Judge Simons served on the Liberal Arts Advisory Committee for Berkshire Community College and is an active member of both Knesset Israel Synagogue and the Jewish Federation of the Berkshires. An avid cyclist, he proudly rides the Pan Mass Challenge each year to raise funds for the Dana-Farber Cancer Institute.

Education

• Boston University School of Law, JD, 1985
• Union College, BA, cum laude, 1981

Memberships

• Massachusetts Bar, 1986 – present
  
• U.S. District Court for the District of Massachusetts, 1986 – present
  
• U.S. Supreme Court Bar, 1999 - present
  
• Massachusetts Bar Association, 1990 - present