After he was admitted to the bar, Bob entered private practice in 1988 and has been a partner in Helbock & Nappa, LLP since 1994, formerly known as Helbock, Nappa & Gallucci, PLLC. He has handled a variety of cases in his 31 years as an attorney, including commercial, landlord-tenant, personal injury defense, guardianship, probate and administration, trusts, workers compensation, and social security disability.

While maintaining his law practice, he began serving as legislative counsel to the great State Senator John Marchi in 1989. Bob served in this capacity until Senator Marchi’s retirement in 2006. Bob’s work in politics also saw him head the Staten Island Republican Party as Chairman from 2003-2006 and as Law Chairman to several other SIGOP Chairs.

Bob’s has also provided extensive community service to his home borough. He is a longtime member of the Richmond County Bar Association and has been on its Judiciary Committee for the last two years. Bob is a former Member of Staten Island Community Board 1, where he served on the Social Services and Land Use Committees. For over 20 years, Bob has been a coach or referee for the Catholic Youth Organization (CYO), Catholic High School Athletic Association (CHSAA), and the Amateur Athletic Union (AAU).

Bob is a former trustee for the Blessed Sacrament Parish and is currently the Chairman of the Fund for the Advancement of Mental Health on Staten Island. 

Bob was married for 27 years to Jeanne Helbock who passed away in 2017. Together, they raised two children Robert, 22, a graduate student, and Bridget, 19, a college undergrad. Bob and his family have lived in Silver Lake, Randall Manor, and now West Brighton.