For a man with a history of personal foibles and a string of losses at the ballot box, Tony McConkey drew a surprising share of the vote in the Republican primary for House District 33A. He beat a rival with deeper pockets and a squeaky-clean past. And he piled up nearly as many votes as the Republican incumbent, Del. David G. Boschert, a fixture of Anne Arundel County politics.

Political handicappers from both parties credit McConkey's aggressive campaign and a succinct message - "anti-tax, pro-gun, pro-life" - with winning over the party stalwarts who turn out for primaries.

But as the race has moved past the primary, McConkey, 38, has had to publicly answer uncomfortable questions about matters he had hoped were long behind him: his voluntary disbarment from the practice of law, the state's revocation of his real-estate license and several minor tangles with police.

This history has haunted McConkey in past races, and Democrats are reviving it again as they angle to place one of their own in the staunchly Republican two-member district stretching from Severna Park to upper South County.

"It represents a real opportunity," says David R. Paulson, spokesman for the Maryland Democratic Party, which is advising the party's candidates in 33A, James H. Snider and Steven D. Rizzi. "I don't think McConkey is somebody that the voters of Anne Arundel County or any county would want to send to Annapolis."

But the attitude among Republicans - some of whom shunned McConkey when the disclosures came to light several years ago - has been to forgive and forget. McConkey appears in ads, lawn signs and mailings for "Team 33," the GOP slate headed by Del. Janet Greenip, who is giving up her House seat to run for the state Senate.

Greenip said she met with McConkey the day after the primary and came away convinced that he has outgrown the "impetuous" phase that landed him in rough water in the 1990s. He has since won back his real estate license, she noted, and has become a thoughtful, hard-working activist for the party.

"He has, in my estimation, redeemed himself," she says.

McConkey's troubles stem from a failed real-estate deal in Prince George's County in the late 1980s. McConkey acknowledged in a legal decree several years later that he had "failed to maintain and account for funds entrusted to me." And an administrative law judge found that McConkey "was not entirely truthful with his partners."

In the 1990s, McConkey was charged twice with battery and once with fourth-degree burglary, a misdemeanor. The two battery charges were dropped. But as part of a deal with prosecutors on the burglary charge, McConkey paid a $200 fine, performed 20 hours of community service and received probation before judgment.

In recent candidate debates, McConkey has described his troubles as a "learning experience." He says the criminal charges were trumped up by tenants he was evicting as a property manager in Prince George's County.

"I was managing ghetto properties and I had drug-dealer tenants," he said in an interview last week. "It was a nightmare. I got out of it quickly."

The burglary complaint was filed in 1994 by a tenant at a house he owned who claimed he harangued her about the rent and kicked in the door as she attempted to close it.

A Democrat-financed political committee was officially formed Friday to mail voters reminders of these episodes - ones McConkey regards as Paleolithic history.

"I don't see how it's news," says McConkey. "I think they're desperate. They feel they're losing and they're grasping at whatever straws they can."

In a district loaded with so many Republicans, it remains far from certain that the new talk about his past will scuttle his fourth bid for public office. (His previous campaigns were in other districts.)

"It's by no means obvious that the party registration advantage that Republicans hold in 33A will be overcome," says Dan Nataf, a political scientist at Anne Arundel Community College. "It depends on the campaign by the Democrats. A weak campaign and McConkey's in."

One hurdle for the two Democrats, says Nataf, is their relative obscurity.

Rizzi, 39, heads the Annapolis office of Science Applications International Corp., a high-tech firm based in San Diego. Until now, Rizzi's profile on the political scene didn't rise much above his membership on little-known state boards on Internet privacy and high-speed computing. His company is a large government contractor, drawing about $15 million in state business over the past five years, state records show. Rizzi says he will avoid conflicts of interest by handing over the reins of the Annapolis office to a deputy during the legislative session.

Snider, 43, of Severna Park, is a fellow at the New America Foundation, a think tank in Washington. He has a higher profile, mostly because he was the top choice of an independent nominating convention for the county school board. He was passed over for the post after County Executive Janet S. Owens persuaded Gov. Parris N. Glendening to appoint a distant relative of hers, a move that inflamed Snider supporters and has helped electrify his campaign.

Snider was a member of the Burlington, Vt., school board in the early 1990s, and he and Rizzi are now taking aim at the condition of the Maryland public schools. They say they would press for smaller class sizes and a county school board with at least some elected members. The board is now filled by gubernatorial appointees.

Snider says he also wants to move the General Assembly into the Information Age by televising hearings and making it easier to check lawmakers' voting records on the Internet.

The fifth candidate is independent Michael A. Lagana, 37, of Crofton, an account manager at a Pasadena collections firm who gathered 843 signatures to secure a place on the ballot. Disillusioned with partisan bickering and the role of money in elections, he says he is running to restore politics to its rightful place as a "battle of ideas." His chief idea, he says, is shrinking government and simplifying the tax code.

Boschert, 55, the incumbent first-term Republican from Crownsville and former County Council chairman, is expected to hold onto his seat. But 33A is new. It was split from the old House District 33 in response to population shifts measured in the 2000 census. So Boschert has had to introduce himself to new voters, a situation that may explain his relatively soft lead over McConkey in the primary.

Boschert has promoted his sponsorship of bills to toughen penalties for drunken drivers and quicken the enforcement of court orders against batterers.

But he has had his own difficulties. He admitted in April that he broke county ethics rules by working as an unregistered lobbyist in a Severna Park zoning dispute. He agreed never to do it again, and the matter was dropped. Still, the episode has figured recently in newspaper inserts purchased by the Rizzi campaign.

Sun staff researcher Jean Packard contributed to this article.