After winning a Prep School Championship with Milton Academy, Rob O’Gara went to Yale University. He played for four seasons, two as an All American and won an NCAA Championship in 2013. After his Senior Season, Rob signed with the team that drafted him, the Boston Bruins. He made his NHL debut on October 13, 2016 for the Bruins. In February 2018, O’Gara was traded to the New York Rangers. In July of 2019, O’Gara signed a free agent contract in the St. Louis Blues organization.