John A. "Jack" Pini Jr., 73, of Ashland, Massachusetts, passed away peacefully on June 14, 2025, surrounded by his loving family.

Born on June 6, 1952, and raised in Wellesley, Jack was the eldest son of the late John and Serafina "Sally" Pini. He married his high school sweetheart, Barbara (Murphy) Pini, and together they shared over 50 years filled with love, laughter, and deep devotion.

Jack and Barbara built a life rooted in friendship, respect, and a shared love of family. Barbara was his constant companion and greatest supporter. They embraced life together, hosting gatherings, traveling, and enjoying quiet evenings watching the sunset from their porch.

They raised three daughters, whom Jack adored: Kristin (Christopher) Lomuto of Southborough, Jacqueline (Stephen) Trotta of Newton, and Ashley Pini of Westfield. He was a devoted and loving father, endlessly proud of his daughters and their families.

To his grandchildren Gabriella, Rocco, Nicolas, Delaney, and Cameron, Jack was affectionately known as "Buddy." They were the joy of his life, and he never missed a chance to cheer them on at their games or make memories during cherished family vacations.

Jack shared a lifelong bond with his family, including his brothers, Robert and Richard, as well as his cousins. They shared countless memories from sporting events, summers on the Cape, and golf outings.

He graduated from Wellesley High School in 1971, then went on to Bentley University, where he captained the baseball team and graduated in 1975. He was later inducted into the Bentley Athletic Hall of Fame. Jack earned his MBA from Babson College in 1978. He spent many years as an executive at New England Financial, where he formed lifelong friendships. Later, he returned to Bentley to work in development, a role that reflected his warmth and gift for building relationships.

After retiring, Jack worked for the WooSox, blending his love for baseball with his ability to connect with people. In recent years, he found great joy in music, singing and playing guitar and harmonica in a classic rock band that performed locally.

A longtime member of Framingham Country Club, Jack enjoyed his time there with friends and family, golfing, celebrating milestones, and watching his grandchildren at the pool.

Jack will be lovingly remembered by the many family and friends whose lives he touched with his kindness, loyalty, and generous spirit. His presence brought joy and connection to every gathering, and his legacy lives on in the hearts of those who knew him. We encourage everyone to live a little more like Jack, to make the most of each day, and to embrace life with joy, purpose, and connection.

A funeral service will be celebrated Sunday June 22nd at 2:00 PM in the Chapel of the Matarese Funeral Home, 325 Main St. Ashland, MA.  Visiting hours will be held at the funeral home on Sunday from 11:00-1:30 PM prior to the service.

In lieu of flowers, donations may be made to The Jimmy Fund , an organization close to Jack's heart.