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.