The visitation will be live streamed via the attached link, starting at 5PM on Thursday, May 14th: https://client.tribucast.com/tcid/a26055147830827

Paul F. Bailey, 83, of Spencer, passed away peacefully on May 8, 2026, at UMass Memorial Hospital surrounded by the love of his family. Born on August 8, 1942, in Worcester, Massachusetts, he was the beloved son of the late Gwendolyn O. Bailey and William Waller.

Paul lived a life defined by service, leadership, compassion, and devotion to his family and community. A proud veteran of the United States Army, he carried the values of integrity, discipline, and commitment throughout every chapter of his life.

Following his military service, Paul pursued higher education and earned his associate’s degree in business from U-Mass Amherst, beginning a distinguished professional career dedicated to improving the lives of his community. He served for more than 25 years as Chief Executive Officer of Springfield Partners for Community Action, where he transformed and expanded programs that provided critical support to thousands of families. Prior to his work in Springfield, Paul also served for more than a decade as Deputy Director of the Worcester Housing Authority, continuing his lifelong mission of advocating for the underserved population. His work touched countless lives and left a lasting impact across the Commonwealth.

While Paul’s professional accomplishments were many, the role he treasured most was that of a husband, father, grandfather, great-grandfather, brother-in-law, uncle, mentor, and patriarch. He was a steady source of wisdom, strength, humor, and unconditional love. He taught his family the importance of honesty, respect, perseverance, and always doing the right thing, even when difficult. He made countless sacrifices without hesitation and led by example through quiet strength and compassion.

Paul found immense joy in his family and took tremendous pride in every accomplishment, milestone, and moment shared with his family. His love and guidance shaped generations and created a legacy that will continue long beyond his years.

He leaves behind his beloved wife of 41 years, Carmen (Rosado) Bailey, with whom he shared a lifetime of love and partnership, and his loving children and their families.

Paul leaves behind his cherished children: Michael Bailey and his partner, Pari Omidbakhsh; Christine Massenburg and her spouse, James Massenburg Sr.; Robert Bailey and his partner, Sherrell Cooley; Jeffrey Bailey and his spouse, Terasa Bailey; Luis Morales of San Diego, CA; and his youngest daughter, AnnMarie Bailey. He was also survived by his daughter-in-law, Erika Alston of North Carolina. He was predeceased by his beloved daughter, Michelle Bailey, his son, Paul F. Bailey Jr., his beloved granddaughter, Kaiyah and grandson, Zyaire. Paul was also predeceased by his two brothers, Walter Bailey and Robert “Bart” Bailey.

Paul’s family was the center of his life. He was the proud grandfather and great-grandfather of a large and loving family, including 21 grandchildren and 15 great-grandchildren, each of whom brought him immense joy, pride, and love. 

He will be remembered not only for the work he accomplished, but for the lives he changed, the wisdom he shared, and the love he gave so freely. To know Paul was to know kindness, humility, resilience, generosity, and quiet strength. His legacy lives on in every person he encouraged, every family he supported, and every life he touched.

Family and friends are invited to celebrate Paul’s life during visiting hours on Thursday, May 14, from 5:00 p.m. to 8:00 p.m. at the Callahan, Fay & Caswell Life Celebration Home, 61 Myrtle Street, Worcester. A service will be held during the evening visitation.

Burial with military honors will take place Friday, May 15, at 12:30 p.m. in the Massachusetts National Cemetery, Connery Ave, Bourne,MA.

In lieu of flowers, the family asks that donations in Paul’s memory be made to the Springfield Partners for Community Action, at www.springfieldpartnersinc.com/how-you-can-help/continuing his lifelong mission of supporting families and strengthening communities.

May he rest peacefully, forever reunited with those who went before him and forever remembered by all who loved him.