Robert F. Flanagan, Sr., age 92, of Brockton, passed away on July 25, 2024, at the Good Samaritan Medical Center. He was the husband of Elaine (DeSimone) Flanagan for the past 41 years.
Born and raised in Brockton, Massachusetts he was the son of the late John and Edith (Susi) Flanagan.
He graduated from Brockton High School in 1949, then attended Dean Academy, and graduated from Boston College in 1955. Professionally, Bob taught history and coached high school football from 1955 to 1962 at Cranwell Preparatory School in Lenox, Stoughton High School (1962-1967), and Brockton High School (1968 to 1976). After coaching, he obtained his Master’s Degree in Education at Bridgewater State College and continued his career in Brockton Public Schools as an Adjustment Counselor until his retirement. Throughout his career, Bob was very involved in his community, establishing several programs for the betterment of the population.
In addition to excelling in the classroom, Bob was a highly decorated athlete. At Brockton High School he helped his team win the National High School Football Championship. He continued his athletic career at Boston College, where he played both football and baseball. After college, he played semi-professional baseball in Glace Bay Canada alongside his brother Jack before beginning his teaching, coaching, and counseling careers. In 1977, Bob was inducted into the Brockton High School Hall of Fame and in 2023 he was honored at Boston College Alumni Stadium.
Some of his interests included reading (especially history), listening to music, and watching sports, particularly Boston College Athletics.
In addition to his wife, his legacy continues in his children, Terri Ford of North Falmouth, Kathy Engles also of North Falmouth, Nancy Webb of Colorado Springs, CO, Patty Strangis of Fall River, Joan King, of Taunton, MA, Maura Roberts of Middleboro, Kevin Flanagan of Brockton, Bob Flanagan of Westwood, Michael Flanagan of Provincetown, and Kaleigh DeSimone of Honolulu, HI; twenty-four grandchildren and twenty-four great grandchildren. He was the father of the late Kristine Flanagan-Shapiro and brother of the late John (Jack) Flanagan.
Relatives and friends are cordially invited to attend Bob’s Mass of Christian Burial on Thursday, August 8, 2024, at 10:00 am, in the Chapel of Mary at Stonehill College, North Easton, MA.
In lieu of flowers, donations in Bob's memory can be made to Elaine Flanagan’s participant page for the Dana-Farber Cancer Institute’s Jimmy Fund Walk. Please visit the following website: 2024 Boston Marathon Jimmy Fund Walk: Mrs. Elaine Flanagan's Fundraising Page - Boston Marathon Jimmy Fund Walk or https://danafarber.jimmyfund.org/site/TR?fr_id=2150&pg=personal&px=1019939
For online condolences, please visit us at www.conleyfuneralhome.com or on Facebook at Conley Funeral & Cremation Service.