Cantor’s father, Eddie, a lawyer, ran a successful real estate company. He was also active in Virginia Republican politics and had close ties to Richard Dudley “Dick” Obenshain, who recruited numerous Virginia Democrats to the GOP. As a teenager, Cantor helped with the grunt work of campaigns—stuffing envelopes and putting up yard signs.
The seminal political experience of Cantor’s youth was the 1980 election of Ronald Reagan as president. “Reagan was my inspiration,” says Cantor, who was 17 when the Gipper was elected. “I wasn’t even old enough to vote yet, but somehow he sparked something in me.” It was an especially euphoric time for Jewish Republicans. Reagan captured 39 percent of the Jewish vote—the highest showing for a Republican since Dwight D. Eisenhower. Eddie Cantor, who served as state treasurer for Reagan’s campaign, attended the Republican National Convention in Detroit and returned to regale his son with stories about the charismatic California governor. “It’s been an interesting sort of upbringing, being a Republican and being Jewish, but I found it allowed me to see America at its best,” says Cantor.
The following year, Cantor laid the groundwork for what would become a critical political alliance. As a freshman studying at George Washington University, he interned for Thomas Bliley, a Republican Virginia congressman, a Catholic and a former Democrat. Bliley liked Cantor, whom he remembers as a “very polite, very smart young man,” and the following summer the political science major drove the congressman around his district as he campaigned for re-election. “Eric was a good driver, and I didn’t kill him smoking my pipe in the car,” recalls Bliley.
After graduating in 1985, Cantor earned a law degree from Virginia’s College of William and Mary and a master’s degree in real estate development in 1989 from Columbia University. It was in New York that Cantor met his future wife, Diana Fine, on a blind date. She was his ideological opposite. Fine came from a prominent family of Florida Democrats, and when they met, she was living in Greenwich Village. At the time, she was working at Goldman, Sachs & Co., where she would eventually rise to be a vice president under Bill Clinton’s future Treasury Secretary Robert Rubin.
The couple settled in Virginia, where Cantor joined his family’s law and real estate firms, founding TrustMor Mortgage, a mortgage brokerage company. In 1992, he was elected to the Virginia State House of Delegates. Legislating from the stately building designed by Thomas Jefferson, Cantor earned a reputation as smart, hard-working and ambitious, juggling as many as 30 bills at a time.