Oswald Webbe Jr was born and raised in Boston growing up in the Field’s Corner part of Dorchester. His mother is a Boston native whose parents moved here from North Carolina to start a family and his father immigrated to Boston from Montserrat when he was a child due to a volcanic eruption.

During his adolescence here in Boston he always felt strongly connected to his neighborhood and community. This would nurture a passion for youth work and community building. Growing up in Dorchester he would also be exposed to the plethora of cultural groups in his neighborhood including a large Black, Cape Verdean, Caribbean and Vietnamese population. This fostered a desire to build community throughout the city and highlight how diverse Boston neighborhoods truly are. 

He graduated in 2016 from Boston Public High Schools, where he went on to attend Salem State University. It was during his time there that he learned about an opportunity to do youth work for the city, leading him down the path to his current position. 

During his free time, Ossie enjoys relaxing in nature and all kinds of physical activities like yoga, hiking, bike riding and playing sports.