Robert E. “Bob” Sullivan passed away peacefully on May 15, 2026, at the Kaplan Family Hospice House. Throughout his illness, he showed remarkable courage, humor, and love for family and friends. He was 86 years old.

Born in Arlington and raised in Cambridge, Bob attended St. John’s Elementary and graduated from Rindge Technical High School. He went on to earn his Bachelor’s Degree from Northeastern University and his Master’s Degree in Criminal Justice from Anna Maria College. Bob often spoke of happy memories growing up in Cambridge, playing with the neighborhood children at Rindge Field, as well as stories of his boxing days.

Bob proudly served in the Marines. Affectionately referred to as “Sully” by his fellow officers, he began his law enforcement career with the Medford Police Department. In 1971, he became an officer with the Metropolitan District Commission (MDC) Police, where he patrolled Revere Beach and surrounding areas on horseback as part of the Mounted Unit. Bob ended his long career in law enforcement as a Massachusetts State Trooper stationed out of Logan Airport, Troop F.

Having a contagious laugh and a wonderful sense of humor, Bob had a personality that just commanded attention. Bob loved telling jokes and dancing. He, his wife Ann, siblings, and friends would go out dancing on Saturday nights. He and Ann enjoyed taking cruises, through which they met many wonderful friends, and were avid golfers. Bob also loved playing card games.

A passionate Boston sports fan, Bob was always sure to catch the Red Sox or Bruins games, all while telling the team how they could improve. He could always be seen wearing some sort of Red Sox apparel. In the summer, Bob enjoyed sitting outside on his patio reading his daily paper, completing a Jumble and crossword, or grilling. Bob was very interested in history and enjoyed debating politics. At the end of the day, he enjoyed watching old shows, such as “The Three Stooges,” “The Honeymooners,” and “I Love Lucy,” or a western. Bob also thoroughly enjoyed his Wednesday morning breakfasts with his friends from the force.

Above all else, Bob was a true family man. He was the steady anchor through good times and bad. Always being the one to call in times of trouble, when looking for advice, or when just needing someone to listen. During his retirement years, Bob could always be seen on a softball field, cheering on his granddaughter, or during the week in the driveway practicing with her. After becoming a great-grandfather, Bob had a new light in his life, John Robert. He adored his visits and treasured every second he had with John.

Bob was the son of the late Humphrey and Lois (Moses) Sullivan. He was the beloved husband of Ann (Stevens) Sullivan for just short of 62 years. He was the devoted father of Carol (Sullivan) Donoghue and Kevin Sullivan. He was also the cherished grandfather of Melissa (Donoghue) Murray and her husband, John, and great-grandfather of John Robert.

Bob is survived by his sisters Barbara Caruso, Patricia Guzzetti, and Lois Ann Levesque and her husband Claude, and brother-in-law Lou Monaco. He is predeceased by his brothers John (“Jack”) and William (“Billy”) Sullivan, his sister Elizabeth (“Bette”) Monaco, his brother-in-law Enrico (“Henry”) Caruso, as well as his nephew John (“Jackie”) Sullivan. Bob also leaves behind many loving nieces and nephews.

Visiting hours will be held on Friday, May 29, 2026 from 4:00 PM - 7:00 PM at the A.J Spadafora Funeral Home, 865 Main Street, Malden. A Mass of Christian Burial will be held on Saturday, May 30, 2026 at 10:00 AM at St. Francis of Assisi Church, 441 Fellsway West, Medford. Interment will be at Oak Grove Cemetery, 230 Playstead Road, Medford. Family & Friends respectfully invited to attend.

He will live forever in the hearts of those who knew and loved him.

In lieu of flowers, please consider making a donation in Bob’s memory to St. Jude Children’s Research Hospital.