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With his high sidewall haircut and two-tone glasses, Jim Gilmore was – well, in today's terms, a band geek.
(1966 File Photo)
The Outsider
Page Two of Four

Like many migrations, it began with the Old Country. James S. Gilmore III was born October 6, 1949, in Richmond. His parents lived at Robinson Street and Park Avenue in the Fan, across from the Robin Inn, just down the block from the New Central Barbershop and Cavedo's Drugstore, and only a few blocks from William Fox Elementary School, then the city's best.

Though racially segregated, the Fan was a sociological mishmash – modest row houses and frame shacks standing only a few blocks over from the mansions of the rich on Monument Avenue. For many who grew up in that place and time, the Fan – with its tranquil, angled streets surrounding triangular parks, its mom-and-pop stores and neighborhood eateries, its vegetable and fruit sellers in horse-drawn carts – remains a golden memory. But Jim Gilmore's parents were sharing a home with his mother's parents. And Robinson Street, he recalls, "was a pretty major thoroughfare and there was a lot of foot traffic and there were a lot of people going up and down that street my parents weren't very comfortable with. So after a while they decided they wanted to go to the suburbs and so off we went."

The Gilmores were part of a great demographic upheaval that was transforming American life. In other cities, the migration to the suburbs created places like Levittown and Shaker Heights; in Richmond, it spawned Henrico County. On a map, Henrico has a shape somewhat like a limpet, bordering the city of Richmond on three sides – west, north and east – above the James River. In 1950, it was made up of farms, crossroads and tiny market towns. Even the county courthouse was located in downtown Richmond, to make it easier to reach.

But by 1960, Henrico had more than doubled its population. Most dramatic was the explosion of wealthy homes along the James River to the west, where River Road cut a swath of privilege among institutions like the Country Club of Virginia, the Collegiate School and All Saints Episcopal Church, newly relocated from the inner city. But farther north of the river was another Henrico – a yeasty mix of tract homes where working people like the Gilmores could break free of the crowding, drabness and uncertainty of city life. "It was kind of nifty," Jim Gilmore remembers of his new home. "It was a brand-new ranch house."

The neighborhood was called West End Manor. It was nowhere near the river; instead, it was a few miles from Two Guys discount store, the city's first shopping mall and its first McDonald's. Gilmore's father worked at Safeway, his mother at the Methodist diocesan office.

With his high sidewall haircut and two-tone glasses, Jim Gilmore was – well, in today's terms, a band geek. His entry in the 1967 yearbook of J.R. Tucker High School lists him as student band director, drum major of the marching band, president of the concert band, and a member of the All-County, the All-Regional and the All-Student USA bands. "All I did in high school was play music," he recalls.

But the All-Student USA Band marked a turning point. When the time came to parcel out the solos, Gilmore came up against another clarinetist who literally blew him away. "This guy was so effortless, because he was truly gifted," Gilmore recalls. And he realized that he would never be that good, or even close. For Jim Gilmore, that was the day the music died.

What took its place was politics. Gilmore's Key Club adviser asked him to help get out the vote with door-to-door canvassing. "I wasn't old enough to vote but I was influencing so many others to vote," he recalls. "Suddenly I was on."

"Being a Young Republican then," Stan Maupin says, "tempered you like steel."

Maupin, a Richmond investment banker, met Jim Gilmore in 1967, the year they both entered the University of Virginia. Their classmate George Allen was a backup varsity quarterback; Gilmore joined College Republicans. "We were always looked on as nerds," Maupin recalls. Gilmore spent his Friday nights at the Jefferson Literary and Debating Society, a conservative club. But he saw himself as a rebel. He despised what he saw as "an abiding sense of arrogance in the Democratic Party. Something in my personality reacted against that."

Gilmore's visceral dislike of Democrats makes sense only in the context of Virginia history. Until the mid-1960s, the state was run by an oligarchy as tidy and rigid as that of Stalinist Albania. Political power passed from well-heeled father to well-born son, Working people and minorities were on the outside. Poll taxes and literacy tests were formidable obstacles to voting; often only 10 or 11 percent of eligible voters cast ballots. "By comparison," political scientist V.O. Key once wrote, "Mississippi is a hotbed of democracy."

Harry Byrd Sr. and his followers rejected the very notion of a two-party system. During his Democratic days, then-Gov. Mills Godwin told the faithful that "one Republican in the General Assembly is one Republican too many." Although Godwin later switched parties, outsiders like Jim Gilmore have never forgotten the days when they were powerless outcasts.

While at U-Va., Gilmore met Roxane Gatling, a classics student from Suffolk. Ever the party animal, he invited her to join him canvassing door-to-door for Republican candidates. They were married in 1977, and now have two children. Roxane Gilmore teaches ancient history at Randolph-Macon College in Ashland. She is working on her PhD dissertation, a study of the role of religious cults in the early days of Athenian democracy. "Jim Gilmore is not the most conservative one in that marriage," a family friend says.

After college, Gilmore enlisted in the Army and requested intelligence training. The Army taught him German and sent him to Mannheim, Germany, as a sergeant. Counterintelligence "was pretty interesting work," he recalled. As his term drew to an end, he considered a career with the CIA.

But there were still accounts to settle with those arrogant Democrats back home. All through his Army years, he corresponded with the admissions office at U-Va. Law. Each time he got a commendation or passed a new skills course, he dropped the news in the mail to Charlottesville. It didn't work, though; he was turned down for the Class of 1977. Instead, he enrolled at the less prestigious T.C. Williams School of Law at the University of Richmond.

But when the first day of classes at U-Va. came around, he was firmly planted in the admissions office of the law school. The dean of admissions remembered all those letters from Germany, and let him in on the spot. At U-Va. Law, he was up against students who could riff on torts and constitutional law like that long-ago soloist on the clarinet. Gilmore wasn't brilliant like that; he was a plodder. "It was pretty tough going, to tell you the truth, but I kept at it," he recalls. "I got it after a while."

After law school, he found the world of the downtown law firms – the patrician legal factories that produced governors and judges as readily as wills and debentures – was not open to a middle-of-the-class kid from West End Manor. "They had the pick of Virginia and Washington and Lee and places around the country and they had people that they knew very well," he recalls. "I'm not in any of that universe."

Eventually he settled into a small firm just over the Henrico line and plunged into politics.

By the late 1970s, Henrico had nearly caught up to Richmond in population. It was also the most solidly Republican county in the state, voting reliably 3 to 2 GOP in statewide and national races. In 1980 Rep. David Satterfield, a popular, far-right Democrat, announced his retirement after 16 years in office. Republicans recruited Tom Bliley, the conservative former mayor of Richmond, as their candidate. But Bliley was a former Democrat, and the local organization wanted one of its own to run the campaign. The choice went to Boyd Marcus, a friend of Jim Gilmore's from college (now his chief of staff). And so was born the "Bliley mafia," a network of bright, young, white suburban Republicans who allied with Bliley in building the party organization, recruiting candidates and enforcing party discipline. Prominent among them was Gilmore, who quickly became a close friend of Bliley's.

In 1987, Gilmore ran for county prosecutor-commonwealth's attorney. It was, he recalls now, "probably the hardest race I've ever run." His opponent, former assistant prosecutor L.A. "Al" Harris, had been appointed by the county judges – all Democrats – to fill a sudden vacancy. It was the traditional Virginia way of passing on authority, which was expected to flow down from the courthouse rather than up from the grass roots.

"During the race I was looked on as something of an interloper," Gilmore recalls. He didn't have much of a record as a criminal lawyer. But he had the drive to get out and knock on doors, to stand in shopping centers day after day offering brochures to apathetic strangers. "That's not something that a lion of the criminal bar would necessarily have been able to do," Gilmore says.

Soon after taking office in 1988, he received a letter from a local physician asking for guidance about state law. The doctor had a comatose patient in a local nursing home whose family wanted him to withhold life support. The patient had no hope of recovery, but the doctor wondered what his legal position would be if he ordered nutrition and water withheld.

Gilmore's close associates report that he often takes a long time to make important decisions. "He did agonize over that case," says Gary Aronhalt, then an assistant in the commonwealth's attorney's office and now secretary of public safety in Gilmore's Cabinet. "It was on his mind for a substantial period of time – first one way and then the other. It was absolutely not a religious matter. It was a question of the law."

Gilmore concluded that, as the Virginia statutes then read, a doctor who withheld life support would be guilty of homicide. Though the case never became public knowledge, both Gilmore and his associates say it made a deep impression on him, one that would later play a role in his response to the high-profile Hugh Finn case when he became governor.

As prosecutor, Gilmore made converts of his political enemies at the courthouse. "I think he's a good manager," says Al Harris, the man he defeated, now a county judge. "He left on very good terms, and I never saw any big mistakes."

By the time he was reelected in 1991, Gilmore had established his reputation as a law and order prosecutor. Now he began a two-year crusade to take his act statewide, as the Republican candidate for attorney general.


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