Michael Riean Gillespie

Westbrook - Michael “Mikey” R. Gillespie, 68, died on October 17, 2023 after a courageous battle with cancer. Michael was born on September 2, 1955, in Portland, the son of the late William E. and Evelyn (Nute) Gillespie Sr. He grew up in Portland, attended local schools and graduated from Portland High School, Class of 1974. After high school he joined the Army, serving in Fort Benning, GA. He was awarded recognition upon graduating from boot camp for marksmanship and long distance running. Michael married Glenda Demers in 1979 and eventually they moved to Westbrook to raise their three kids. He worked many jobs, but he was most proud of his 20 years spent as Head Custodian at the Portland Public Schools. Mikey was extremely dedicated to this work and never missed a day. He retired in December of 2021. Mikey was very competitive. In high school he was on the track team and loved to swim at The Boys Club. After his service in the military, he proudly followed in his fathers footsteps and coached Little League in Portland and later in Westbrook, for his own son. He loved the game of baseball and was a lifelong fan of the Red Sox. In later years, he could still be found at the Little League fields, cheering on his grandson. He was an avid Dallas Cowboys and Notre Dame football fan and was unreachable on Saturday and Sundays when these games were on. In his free time, he enjoyed watching action movies and crime shows, but most of all spending time with his kids and his grandchildren, who were the light of his life. He was very close to his family, especially his sisters. He had many friends, a few friends that were more like family. John Rinaldi, who was his best friend since birth, Peter Profenno and Paul Profenno. Michael was predeceased by his sisters, Mary Jane, Ellen and Linda; grandchildren, Eric and Kristopher. He is survived by his children, Emily Tibbetts and husband Matthew of Westbrook, Riean Gillespie and wife Amanda of Windham, Kristine Gillespie of Durham, their mother, Glenda Demers and her son Sam DiFazio; grandchildren, Eli and Adam; siblings, Donna Pooler of OH, MaryAnne Weeman of Old Orchard Beach, Patrick Gillespie and wife Anna of Steep Falls, William Gillespie and wife Lisa of Liberty; and many nieces and nephews. A Mass of Christian Burial will be celebrated at 10AM on Saturday, October 28, at the Cathedral of Immaculate Conception. A celebration of Mikey's life will immediately follow the Mass at Profenno's Pub, 934 Main St., Westbrook. Memorial contributions may be made in his memory to the Fisher House, PO Box 230, South Walpole, MA 02071 or online at http://fisherhouseboston.org/