James "Jim" and Mary (DeFillipo) Bollettieri decided to raise their three children, surrounded by lots of extended family, in the predominantly Italian, middle-class neighborhood of North Pelham, New York.

Their oldest child, Rita Mary, is a great student and does extremely well in school. After high school, Rita earns her Bachelors Degree from nursing school.

Their second child, Nicholas James, "Nick", is very athletic and loves people and getting into mischief. Nick hones both his athletic and his social skills in high school. He plays quarterback for his high school football team and dates some of the prettiest girls in town.

Like his older sister, their youngest child, James Thomas, “Jimmy Boy", is an excellent student. Unlike his older brother, Jimmy Boy is asked to serve as an altar boy at their church.

Jim supports his family as a Pharmacist. He is the youngest person to graduate from Fordham University in New York with a degree in Pharmacy. Jim opens Bollettieri Pharmacy on the corner of in North Pelham, New York.

With the help of her mother and numerous other extended family members, Mary stays home to raise their three children, cook fantastic Italian dinners, and make their house a home.

The family share a home with Mary's parents, Frank and Rita DeFillipo. Jim, Mary, and their three kids live on the second floor.

Jim's parents, Nicholas and Mary Bollettieri, live just down the street. Jim's father works as a butcher. Mary's father works as a building contractor. Besides the ever-watchful eyes of their grandparents, the Bollettieri children are also surrounded by numerous aunts, uncles, and cousins.

It wasn't until Nick left for college that Jim and Mary purchased their own home to live in just down the street from their previous home.

During his high school years Nick earned money by working as a caddy at the Hampshire Country Club in Mamorneck, New York. Nick's cousin, Manny Amorsano, was the Caddy Master. They were each paid $6.00 per round plus tips...so, Nick would carry two bags and get paid double!