This week, he will answer the accusations in court.
The charges already have taken a toll on Anne Arundel, leading to the abrupt retirement last year of the police chief, inspiring a lawsuit by the American Civil Liberties Union and casting a shadow over the county's reputation as a place where Naval leaders are groomed and the state conducts its business.
As the trial opens, county officials and taxpayers, allies and critics alike say they are looking forward to some resolution.
"I'll be glad when it's over with," said County Councilman John Grasso, a Republican who praises Leopold's work as county executive. "I hope John prevails in this situation, because he's done well for the taxpayers."
Leopold, 69, was accused by a grand jury last March of using county police officers assigned to his security detail to set up his campaign signs, to collect and deposit campaign contributions, to compile dossiers on political adversaries and to drive him around as he took down the signs of his 2010 challenger.
The veteran politician — he served nearly two decades in the House of Delegates, and in the Hawaii legislature before that — is also alleged to have directed officers to drive him to parking-lot liaisons with a county employee, and to keep his live-in girlfriend from meeting the woman.
Leopold is also accused, in the indictment signed last year by State Prosecutor Emmet C. Davitt, of using an officer and a staff aide to change the urinary catheter bag he used while recovering from back surgeries.
Leopold, who has remained in office while under indictment, is charged with four counts of misconduct in office and one count of fraudulent misappropriation by a fiduciary. If convicted of the fraud charge, he could be sentenced to up to five years in prison. Judges have broad leeway on sentences for misconduct in office because there is no specific penalty.
The county executive has denied any wrongdoing. He declined, through a spokesman, to comment for this story.
Councilman Jamie Benoit, a Democrat, has been critical of Leopold. He called the charges a "distraction" and says they have affected the way he views personnel actions and other initiatives coming from the administration. He sees the trial as a step forward.
"One way or another, there will be a very clear resolution," he said. "If he's acquitted, at least the criminal part of this will be done. And if he's convicted, he'll be removed from office.
"To have some definitiveness will help."
News of the grand jury investigation into Leopold's use of his police detail became public in early 2011, and he was already the target of a civil lawsuit by former county employees alleging sexual harassment. But the details of the indictment last March still shocked the county.
During Leopold's 2010 re-election campaign, prosecutors say, he required taxpayer-funded officers to "place, replace and check on his campaign signs" while on duty. The officers earned overtime for such work on the weekends. Officers complained on several occasions to superiors in the Police Department including Police Chief James E. Teare Sr., prosecutors say, but no effective action was taken.
Prosecutors say Leopold directed officers to create dossiers on Democratic challenger Joanna Conti and Annapolis civil rights activist Carl Snowden. The officers did not consider either to be a security risk.
Following the indictment, the county's largest police union voted overwhelmingly to express no confidence in Leopold and Teare. Teare agreed in July to retire after nearly 25 years with the department, ending a criminal investigation of his role in the case against Leopold.
The ACLU of Maryland and 11 individuals including Snowden filed a lawsuit last month demanding a full accounting of what the organization called Leopold's "enemies list." The plaintiffs allege that information on Leopold's perceived political rivals, employees, and community members was gathered improperly, and withheld when requested by individuals who had reason to believe they were targeted.
O'Brien Atkinson, president of the county chapter of the Fraternal Order of Police, said the department has weathered a tumultuous two years.
"When the chief of police has his retirement announced by the Office of the Maryland State Prosecutors, that certainly has an effect on morale," he said. The prosecutor's office conducts investigations into public corruption, election law violations and misconduct by public officials, among other crimes.
"I think that we knew from the very beginning of all this that the end result would be a cloud over the Police Department," he said. "It hurts every single officer because it changes the perception from every citizen to every officer out there working the streets."
Atkinson said it was time to "put this behind us as quickly as possible, whatever the outcome."
Dan Nataf, director of the center for the Study of Local Issues at Anne Arundel Community College, said the uncertainty about Leopold's fate is "undermining the ability of county government to focus on its core mission."
"Right now we're focused on who's going to lead," Nataf said. If you're doing business with county government, he said, "you don't know how much to invest in Leopold or his office. … You're just not sure whether you're going to be dealing with the same set of actors that you're dealing with now."
Ashley Heffernan, chairwoman of the Anne Arundel County Democratic Central Committee, called the charges against Leopold "a very negative distraction."
"The news around the state about the county is about the county executive and his problems," she said. "And to me, that's embarrassing."
Grasso, the Republican county councilman, said the charges have had "no impact whatsoever" on county government.
"The government doesn't depend on any individual," he said. "One person leaves, one person gets in trouble, it doesn't stop anybody coming into work, doing their job and going home.
"The county executive could be gone for months, it wouldn't matter whatsoever, because everybody else is in place, knows their job, and what they're to do."
If Leopold enjoys a political stronghold, it's in northern Anne Arundel, where he makes his home, where he is known for strong constituent service going back to his days in the legislature. Voters in that part of the county have elected and reelected him county executive with double-digit margins.
Over coffee at the 3 B's Bakery & Lunch in Pasadena one morning last week, some of these neighbors made their feelings clear: They're ready for his trial to be over already.
"It's so we can all move on and it put to rest," said Santa Callahan, a 73-year-old Democrat from Orchard Beach who said she has voted for the Republican Leopold. "I'm tired of hearing about it."
Callahan said Leopold helped her daughter-in-law get a sign posted on her street to alert drivers to a child with special needs — her granddaughter.
"Nobody would help her," she said. "He did."
Donna Braun, 60, a retired Motor Vehicle Administration customer service agent from Glen Burnie, remembered Leopold sending her condolence letters on the deaths of her father and brother.
"I think that he is being made to be an example," she said. "He is saying he is innocent, and people still support him."
Braun said the case doesn't appear to have affected county services, but have "hurt the county's image."
At this point, she said, "It should be over with."