John R. Leopold almost moved to Manhattan's Lower East Side -- to paint.

He learned Mandarin Chinese from a former Miss China, a contestant in the Miss Universe pageant.


And his favorite sportsman is retired Philadelphia Phillies third baseman Mike Schmidt. A poster of Schmidt downing a carton of milk used to hang on the basement wall of Leopold's Pasadena town house.

Leopold, a two-term delegate to the Maryland General Assembly, is perhaps best known to District 31 voters as the tall, lanky figure standing on the side of the county's highways for the last eight years, waving a "Leopold & You" sign at passing motorists.


He has knocked on their front doors and sent them condolences when relatives have died. And he has dominated news headlines, garnering more ink than any of the county's other 18 delegates and state senators.

However, as a candidate for the District 31 Senate seat, Leopold remains something of a mystery.

Since Leopold won a seat to the Hawaii House of Representatives 20 years ago, his opponents have described him as a self-serving opportunist; his advocates have portrayed him as a political maverick who listens to his constituents and is unafraid of bucking the system.

And everyone says he's ambitious.

"Delegate Leopold is smart, competent," said John Kabler, regional director of the Clean Water Action Project, a national environmental lobby that has endorsed Leopold's opponent, state Sen. Philip C. Jimeno. "But he seems to misuse, to misdirect his abilities in the legislature. He uses his competence and his abilities to grab the spotlight and to take credit for others' work."

"I think he's a smart politician," agreed Delegate John Gary, R-Millersville. "But there is a difference between being a smart politician and being an effective legislator. He could have been one of the most effective legislators down (in the General Assembly) if he had been more of a team player."

"He made members of the majority party embarrassed because he always did his homework," said Hawaiian state Sen. Mary George, a Republican colleague during Leopold's four years in the Hawaiian Senate. "He worked 24 hours a day. That's always embarrassing to those who just try to slide by."

"He spends 99 percent of his time thinking and talking about politics and public policy," said Delegate Robert Kittleman, R-Howard County. "He probably even dreams about those things. They consume his life."


Sitting in a corner booth at the Severna Park Hardee's last week, Leopold retraced the events in his life that brought him to the Senate race.

He had declined to be interviewed at his new Elizabeth Landing town house. And he prefers the booth at Hardee's to the small office the state provides him in Annapolis.

It is the same booth, Leopold said, where he told former U.S Representative Marjorie Holt and former Delegate Robert Neall last spring that he would not run against Neall for the GOP's county executive nomination. He abandoned his three-year-old bid for county executive because opinion polls indicated he could not defeat Neall, but would fare much better against Jimeno in the Senate race.

Leopold, 47, said he was born into a decidedly non-political Philadelphia family. His father, Irving Henry Leopold, is an internationally renowned ophthalmologist. His mother, Eunice Robinson Leopold, is a Baltimore native. They now live in Newport Beach, Calif.

Even Leopold, who has touted himself as a full-time legislator in both Hawaii and Maryland, toyed with careers in creative writing, painting and journalism before launching into politics.

Graduating with the 200th class of Philadelphia's Germantown Academy, Leopold won the private high school's literary prize for a poem comparing the works of Henry David Thoreau and T.S. Eliot, his favorite poet.


Later, at New York's Hamilton College, Leopold split his time between sports -- he played varsity soccer and baseball -- and the arts. An English major, he served on the board of the school literary magazine and developed an interest in abstract painting.

After his college graduation in 1964, he headed to the New Jersey Shore to work a summer job at the Long Beach Daily Reporter.

"I've always been fascinated by the world of journalism," Leopold said.

"Recently, I've been thinking a lot about television as a way to combine my interest in public affairs and the arts."

Before finally accepting a job as a research assistant and speech writer for former U.S. Sen. Hugh Scott, R-Pa., a young Leopold considered moving to a loft in Manhattan's Lower East Side and living an artist's life.

Leopold said he had sold several paintings to galleries in Philadelphia and Iowa, "which I would love to have back right now."


"There's a painting I sold for a three-piece suit in a store in Iowa City," he said.

Last week, while campaigning in Laurel Acres, Leopold said he met a constituent -- for the first time among the thousands of doors he has knocked on -- who knew his favorite artist, Nicholas de Stael, a Hungarian abstract painter.

While working in Washington for Senator Scott, a collector of Oriental art, Leopold said he developed a fascination with Far Eastern culture and decided to learn Mandarin Chinese. After trying to teach himself the language during evenings at the Library of Congress, Leopold enrolled in a nine-week crash course at Seton Hall University and, later, graduate classes at the University of Pennsylvania.

At Seton Hall, Leopold dated his professor's daughter, a former Miss China in the Miss Universe pageant, who helped teach him the language. "She spoke fluent English, but she would allow me to speak Mandarin Chinese with her," he said.


By 1967, Leopold had decided to give politics a try -- but was too young to qualify for thePennsylvania legislature or Philadelphia City Council. So he packed his bags and headed for Hawaii, where he had been offered a job teaching English and Mandarin Chinese at Saint Louis High School, a parochial school linked to Chaminade University.


No sooner had his plane landed and he checked into a boarding house than he sought out his new state's Republican headquarters. Leopold's storied political career had begun.

In 1968, Leopold ran for the state Board of Education. He had hoped to run for the Hawaiian House of Representatives, but the rules required that he live in the state three years. For the school board, he needed only one.

An unknown in a heavily Democratic state, Leopold introduced Hawaii to a new form of campaigning -- standing on street corners, waving signs bearing his name. The effort paid off, as he became the only Republican ever elected to the school board.

"I remember going back to the boarding house, waking up all the old men who lived there and drinking champagne," Leopold recalled.

Although the school board job was not salaried, the state paid a stipend for every meeting he attended. Leopold quit his teaching post to devote himself full-time to his political career.

"I was single and my expenses were very low," Leopold said, noting that he drove the same Volkswagen Beetle during the entire 14 years he lived in Hawaii.


Leopold, who earns $24,000 annually as a Maryland delegate and currently holds no other job, said he inherited some family money which he has invested in property, stocks and savings accounts over the years. He also draws a pension for his 10 years of elected service in Hawaii.

In 1970, Leopold set his sights on the state House of Representatives.

Having established his name in Hawaii, he focused on meeting voters face to face at their front doors. He won narrowly.

Leopold became a frequent critic of public utilities, the Democratic majority and many of his Republican colleagues, whom he accused of collaborating with the Democrats.

"He was quite a self-promoter," recalled Richard Borreca, political editor of the Honolulu Star-Bulletin. "It was attention from the press. He had to have it. He was just a constant fountain of press releases."

His first wife, Maureen, an outspoken feminist, also grabbed her share of headlines, Borreca said. "She wore a little gold necklace that said, 'F--- Y ---.' That went over big with other Republicans," he said.


Leopold, who has been married three times, declined to comment about Maureen. "I don't want to talk about my wives," he said. "I don't see how they have any bearing on performance in public office."

Although Leopold -- who Borreca said was considered a "liberal Republican" -- alienated many of his colleagues, he easily won re-election in 1972. In 1974, he won a seat in the Hawaii Senate.

"Very little got past him," said Senator George, Leopold's colleague in Hawaii. "Every product that come out of one of his committees bore the imprint of his stamp."

George said Leopold was particularly well known as an activist for women's issues, including abortion rights. "Back in the early 1970s, he was on the right side of all the issues," she said.

Leopold, who has been endorsed by anti-abortion groups since he has been in the Maryland General Assembly, said he has never favored unrestricted abortions. He said he never had to vote on abortion in Hawaii, which legalized abortion the year before he was elected to the legislature, and never formed an opinion until he moved to Maryland in 1982.

He said he worked with Planned Parenthood in Hawaii because he believes in sex education and family planning.


Asked if Leopold's anti-abortion stand surprised her, Senator George said, "No, I probably spoke too soon about the choice issue. The big issues in our state were the inability of women to get bank loans, get jobs and get insurance."

In 1978, GOP officials nominated Leopold for governor. Leopold supported the decriminalization of marijuana, registration of handguns and public financing of political campaigns. But the party never fully supported his campaign and he captured only 45 percent of the vote, losing to the incumbent Democrat.

"He was a rebel," said Virginia Isbell, Leopold's running mate in 1978.

"That's one of the reasons he didn't make it. None of the Republicans supported him.

"He had a few contacts and a few people," she said, "but I wouldn't say they were dedicated. If he had more friends, he would have won."

Isbell said she believes Leopold would have made a good governor "because he knows the issues and that's his life." But, she added, "The only reason he runs is that it's the only thing he knows how to do. His motives and goals are simply to perpetuate John Leopold."


Two years later, Leopold decided to seek his old Senate berth as well as a seat at the 1980 Republican National Convention.

The decision angered Senate Minority Leader Wadsworth Yee, who said Leopold had agreed to run for one or the other, but not both. Yee, who has left politics and could not be reached for comment, issued a letter to other Republicans denouncing Leopold, saying he could not be trusted.

While winning a seat to the GOP convention in Detroit, where he captured the national spotlight for his support of the Equal Rights Amendment, Leopold finished a poor third for two Senate seats in his district. Then, Leopold disappeared from sight.


Leopold resurfaced in Maryland in 1982. Appointed by President Gerald Ford to an education advisory panel in 1977, Leopold said he wanted to be closer to the nation's capital.

Settling in the Pasadena community of Chesterfield, Leopold immediately began politicking. Just as in Hawaii, he took to the street corners and waved at passing motorists.


Uncertain at first whether to run for County Council or state Senate, Leopold eventually settled on the House of Delegates. In November 1982, he became the only Republican ever elected from District 31, knocking off incumbent Democrat William Burkhead.

"The most exhilarating day of my political career was the day after my election in 1982," Leopold recalled. "I went out on the road with a 'thank you' sign. The warmth and caring that I was sharing with the motorists was worth so much more to me than wealth or personal gain."

Leopold has fought unsuccessfully against the county's impact fees on new development. He won regional representation on the county Board of Education. He passed a measure barring children access to sexually explicit phone messages. Recently, he has pushed for optional no-fault automobile insurance.

Although many lawmakers like the idea of no-fault insurance, which could lower insurance premiums, "the bill won't pass with Leopold's name on it," Gary said.

"He's probably the most politically astute person I've ever met," said Delegate Gary. "He often has good ideas. And though he can't get them passed, he can get mileage with them out of the press and community groups.

In reality, other politicians aren't saying the same things because they know they can't get them passed."


"This guy's future could have been unlimited if he had been a team player," Gary said. "At just about every opportunity, he's created friction."

Jimeno has hit on that theme again and again, arguing on the campaign trail that Leopold cannot be effective because he has alienated too many lawmakers. "When it comes to doing anything of significance, he can't pull it off," the senator said.

Leopold dismisses the charge as mere partisan politics. "I've never had a problem with politicians of either party who are not threatened by my political candidacies."

Within the district, Leopold has developed an appeal apart from mainline Republicans. To many, Leopold -- who treks door to door year-round -- appears accessible and responsive to their concerns.

"He really cares about the people of the district," said Carol Vitek, a Silver Sands resident and former Leopold secretary. "That's where Phil has hurt himself; he's really concerned about Brooklyn Park with Little League involvement and all."

"My opponent is walking down streets he's never been down in eight years," Leopold said. "I've been down those streets many times."