Benjamin Hillery, Jr Jr

It is with heavy hearts that we announce the passing of Benjamin Hillery Jr., age 62, of Holyoke, MA. Ben was a beloved father, brother, uncle, friend, and advocate for recovery and hope. He passed away peacefully at home on August 3, 2025, leaving behind a legacy of compassion, service, and love.

Originally from Sanford, Florida, Benjamin had recently devoted his life to helping others find healing and purpose. His work with Hope for Holyoke was his calling, and through his dedication, he touched many lives, offering a beacon of support for those on the path to recovery. His passion for this work was evident in everything he did, and his impact will be felt for years to come.

Benjamin was the proud and loving father of two children, Taleara and Donovan, who were his greatest joy. He was a steady, loving presence in their lives, always offering encouragement, wisdom, and unconditional love.

Those who knew Benjamin will remember his warm heart, easy smile, and unwavering belief in the power of transformation. He believed that everyone deserves a second chance and worked tirelessly to make that belief a reality for others.

Predeceased in death by his father Benjamin Hillery, mother Jessie Mae Hillery, and siblings Wilbert Hillery, Ellis Staley, Earl Staley, and Cynthia Hillery.

He leaves to mourn his sisters Eugenia Rose Jackson, Cathy Burke Hillery, and Charlene Gordon (husband Andrew Gordon); uncles Lonnie Hillery and Eddie Jackson; aunts Laverne Jackson Thompson and Gloria Randall; the mother of his children and lifelong best friend Bettyann Womble (Johnson); cherished friends James and Tanya Scurry as well as a host of nieces, nephews, cousins, and dear friends.

He will be deeply missed by his family, friends, colleagues, and the community he served so selflessly. His spirit will live on in the lives he changed and the hearts that carry his memory forward.

A celebration of life service will be held in Benjamin's honor on Saturday, August 30th, from 2:00 p.m. to 6:00 p.m. at the Common Room, 74 First Street, Pittsfield, MA.

Tribute from His Three Sisters: Brother, we love you so much. You were, and still are, an inspiration to us. Thank you for your encouraging words of wisdom, for always being positive, and for reminding us to stay positive as well. We are so very proud of you and the man you became.

With all our love,

Your sisters, Rose, Cat, and Pokey