Robert Harry Flagg, 29, of Boston, MA died suddenly Wednesday April 23, 2021 in Boston after a long battle with addiction and mental illness. He was born in North Adams, MA on March 12, 1992, a son of Seana Flagg and stepson of John DeGraff. He attended University Park Campus School in Worcester, where he excelled. Robert was an adventurer at heart and hated being inside. He was a talented musician and traveled all over the United States, sometimes by vehicle, sometimes by freight train. He loved performing, skateboarding, and especially his dogs, Peach and Nala. Most importantly, he loved his daughter, Felix, and fiancée, Raschel. Survivors include his mother and stepfather- Seana Flagg and John DeGraff of Williamstown, MA; his fiancée- Raschel Rodier Flagg his daughter- Felix Flagg. He leaves his uncle Trevor Flagg, who was his idol and first best friend. Robert also leaves several cousins, extended family, and his traveling family. If you or someone you know struggles with mental health or addiction issues, please seek help. It’s never too late to save yourself or someone you love. FUNERAL NOTICE: A gathering of family and friends will be held on Thursday May 6, 2021 from 2-4 PM at FLYNN & DAGNOLI-MONTAGNA HOME FOR FUNERALS WEST CHAPELS, 521 West Main St. North Adams, MA. Burial will be at a later date. In lieu of flowers memorial donations are suggested in his memory or to the charity of the donor's choice. To add to the Book of Memories, please visit www.flynndagnolifuneralhomes.com.