Robert is the Principal of East Boston Central Catholic. Robert grew up in East Boston and attended East Boston Central Catholic as a child. Robert joined the faculty of East Boston Central Catholic in 1994 as a 6th graduate teacher. 

Robert attended Boston University as a Cardinal Medeiros Scholarship recipient and earned his bachelor's degree in business administration. He earned his master's degree in elementary education from Lesley College. 

Robert was married at Sacred Heart, and his three children were baptised, made their First Communion, Confirmation, and Sacrament of Reconciliation from Sacred Heart. His children also served as altar servers. Robert's children also attended East Boston Central Catholic School.