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Toomey was born on November 17, 1961, in Providence, Rhode Island, the third of six children of Catholic parents, Mary Ann (née Andrews) of East Providence and Patrick Joseph Toomey of Providence. His father was a union worker who laid cable for the Narragansett Electric Company, and his mother worked as a part-time secretary at St. Martha's Catholic Church.
Toomey was a member of the Boy Scouts of America and attained the organization's highest rank, Eagle Scout. His father was of Irish descent and his mother of Portuguese ancestry. His mother's grandparents were all born in the Azores.
Toomey attended La Salle Academy on scholarship participating in the Close Up Washington civic education program. He graduated as valedictorian of his high school class. He graduated from Harvard College in 1984 with an A.B. in government.
In November 1997, Toomey married Kris Ann Duncan. The couple has three children.
After graduation, Toomey was hired by Chemical Bank where he was involved in currency swap transactions. In 1986, he was hired by Morgan, Grenfell & Co., where he dealt in multiple foreign currencies, interest rates, and currency-related derivatives.
In 1991, Toomey resigned from Morgan, Grenfell after it was acquired by Deutsche Bank. He later said he resigned out of concern that Deutsche Bank would impose a less flexible and entrepreneurial work environment. The same year, Toomey and two younger brothers, Steven and Michael opened Rookie's Restaurant in Allentown, Pennsylvania.
In 1994, Toomey was elected to Allentown's newly established Government Study Commission. During his term, he drafted a new charter for the commission requiring a supermajority for any tax increase and established a split-roll tax system that levied taxes on land at higher rate than taxes on buildings. Allentown voters approved the charter on April 23, 1996.