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Michael R. Flanagan

Class of 1990



Michael Flanagan is one of the most outstanding athletes, scholars and philanthropists to have graduated from CHS.

While in high school, Mike was a regular member of the Honor Roll, enrolled in challenging course work, and was a three season all-star athlete.

He was a three-year varsity football letter winner as an offensive lineman. Mike was a 2-time All Merrimack Valley Conference, Boston Globe Division 2 All State selection, and was selected to participate in the annual Harry Agganis Football All Star game. Due to his leadership qualities and respect of his teammates, he was elected as captain in his senior year.

Mike was an outstanding hockey goalie and lettered as a sophomore. A serious knee injury cut his hockey career short. However, he went on to become an outstanding Indoor and Spring Track athlete, participating in the shot put and discus.

Mike’s compassion and early teaching interests were on display as a Physical Education Teacher Assistant working with Special Education students as a senior.

Mike graduated from the College of the Holy Cross in 1994 with a BA in Political Science. While at Holy Cross, he was a 4-year member of the Football team and the recipient of the prestigious Davitt Award as the team’s outstanding lineman as a senior. He has also obtained a MEd in Secondary Education from Fitchburg State College in 2000, and earned his EdD in Curriculum, Teaching and Leadership from Northeastern University in 2016.

At each stop along the way of his educational career as a classroom teacher, coach, building administrator, and now Central Office administrator, Mike proved himself to be an outstanding, effective and tireless advocate educator. For example: He founded The Baystate Principal’s Exchange, a regional collaborative for principals to share best practices and ideas.

He and his wife, Jennifer, turned a very difficult and traumatic family situation into a highly successful and helpful charitable organization supporting pediatric oncology patients and their families at Boston Children’s Hospital. In May, 2005, their son, Connor was diagnosed with mixed lineage leukemia. He would spend the next six months at Children’s Hospital for treatments and a bone marrow transplant. In 2006, Mike and Jennifer began the Connor Flanagan Foundation, which was inspired by their son’s outstanding care and the compassion of the medical staff at Children’s Hospital whose mission is to: Support pediatric oncology patients and families at Boston Children’s Hospital. Again in 2012, Connor had a very serious medical episode that required another extended stay at Children’s. After this stay another floor was included for support from the Foundation.

Since 2006, the Connor Flanagan Foundation (TEAM CONNOR) has raised close to $400,000.00 for Boston Children’s Hospital. Friday Night pizza parties, sibling bags,

a free 24 hour coffee machine, scholarships, gas cards, meals, IPads, games, toys, arts and crafts supplies, and the like have been donated to make hospital life bearable for children on both the oncology and MSICU floors.