Anne Arundel County Executive John Leopold waits before presenting the county's legislative package during a hearing Jan. 11 at the Lowe House Office Building. (Astrid Riecken/FOR THE WASHINGTON POST)

In the annals of Maryland political scandals, the saga of John R. Leopold ranks as one of the most salacious and absurd.

The Anne Arundel county executive, who is scheduled to go on trial Wednesday on charges of misconduct and misappropriating county funds, isn’t just accused of having his security detail ferry him to and from parking lot assignations with his mistress. Prosecutors say the Republican leader of Maryland’s fourth-largest county also had protection officers accompany him on a pre-dawn assault on an opponent’s campaign signs, compile dossiers on rivals and empty a urine bag after back surgery required him to use a catheter.

If convicted, Leopold, 69, could face up to five years in prison. He has maintained his innocence, and his supporters say he is the target of partisan rivals and powerful union interests.

When prosecutors unveiled the charges in March, the allegations surprised many of Anne Arundel’s more than 500,000 residents, said Dan Nataf, a political science professor at Anne Arundel Community College. The man they knew remembered their names — and even their dogs’ names — years after meeting them. He sent notes to his constituents after weddings and Eagle Scout promotions and helped a mother protect her child from bullying at school.

Leopold’s personal life, however, “was foggy,” Nataf said. Until an embarrassing incident in 2009 outside a mall in Annapolis, which offered a hint as to what the county executive might have been up to when he wasn’t governing. That January, a police officer, responding to a 911 call about naked people in a parked car, came upon Leopold fully dressed in the back of his county-issued Chevrolet Impala. Later, police said that the call appeared unfounded and did not file a report.

The next year, in the final months of his reelection bid, a former spokeswoman sued him for allegedly discriminating against female employees, referred to as “Leopold’s Angels.” Other former female employees came forward with similar complaints. (Another filed a separate sex discrimination lawsuit two years later.)

In November 2010, Anne Arundel voters returned Leopold to office, swayed — in part — by the three decades Leopold spent going door to door to visit thousands of constituents. His defenders say he became the target of a vendetta by the county’s public-safety unions when he tried to change binding arbitration rules.

“The unions” and the American Civil Liberties Union — which has filed suit over the dossiers on political enemies — “are persecuting the best county executive we have ever had,” one Severna Park supporter, Barbara Houck, wrote in a letter printed in the Annapolis Capital in July. “He has been totally approachable in his political life, always working for every citizen he serves.”

Leopold is the latest in a succession of Maryland public officials who have gone before a judge in recent years, including former Baltimore mayor Sheila Dixon, who was convicted of stealing gift cards intended for needy families; former Prince George’s county executive Jack B. Johnson, who is serving a seven-year prison sentence for a bribery conspiracy; and former state delegate Tiffany Alston (D-Prince George’s), who was stripped of her seat last year after being convicted of improperly using state funds to pay an employee of her law firm.

What sets Leopold apart, however, is the nature of the scandal. The indictment depicts a man who can’t distinguish between his private life and his professional one.

For some Marylanders, Leopold’s alleged escapades conjure up memories of former governor Marvin Mandel, whose wife — Barbara “Bootsie” Mandel — refused to leave the governor’s mansion for nearly six months in 1973 after the governor left her for another woman. Or of former governor Parris Glendening, whose relationship with his deputy chief of staff while separated from his wife caused a furor in 2001.

For Blair Lee IV, a Silver Spring developer whose father was acting governor, the charges against Leopold remind him more of Bill Clinton, circa 1998. “Isn’t this more of a ‘bimbo eruption?’ ” he asked.

Much like the Starr Report, parts of Leopold’s indictment read like a compendium of normally private episodes of cringe-worthy behavior.

There are shades of Richard Nixon, too. Leopold allegedly had his security detail compile dossiers on potential rivals, many of whom don’t seem terribly threatening. The alleged targets, according to the ACLU suit, include Jacqueline Allsup, head of the county’s NAACP chapter, and Carl Snowden, former civil rights director for Attorney General Douglas F. Gansler.

In the end, a county executive who prided himself on his frugality may have been too cheap for his own good. He allegedly had his security detail put up campaign signs, deposit campaign checks and perform other intern-level chores.

But unlike interns, county police officers earn $40 an hour, and $60 an hour for overtime. In 2010, protection officers allegedly racked up more than $10,000 in overtime keeping Leopold’s mistress and his live-in girlfriend from running into each other at the hospital where Leopold was laid up for two back surgeries. When one of his staffers suggested that he spend $2,000 to hire people to place signs, Leopold rejected the idea, it is alleged.

These days, Leopold drives the Chevy Impala himself. The security detail was disbanded in August.

If he is convicted and tossed out of office, Leopold will be forced to leave the occupation he has devoted the past 40 years of his life to — elective office.

He had served in the Hawaii state Senate and run unsuccessfully for governor there when he and his third — now former — wife, moved to Maryland in 1981.

Leopold settled in Pasadena and and immediately began “shopping around for a political post in Anne Arundel County to fit his talents,” according to a 1982 Washington Post article. He settled on state delegate and won.

Leopold started campaigns for county executive several times, only to back out.

Along the way, he became known for bare-bones campaign tactics that were heavy on attention-grabbing gimmicks and light on paid staff. He stood along busy roads wielding huge signs bearing his name. He regaled reporters with tallies of the thousands of hands he shook and pieces of campaign literature he personally mailed.

In 2003, Leopold again announced his candidacy for county executive. During his successful three-year campaign, he claimed to have knocked on 17,000 doors.

Once in office, Leopold turned his attention to restricting development and trimming the budget.

There was one expense he chose not to cut: the security detail begun by his predecessor, Janet Owens, that was estimated to cost the county at least $125,000 a year. In a post-Sept. 11 world, then-Police Chief James Teare Sr. recommended keeping it in order to protect the county executive from people who might be “angry or have mental deficiencies.”

Leopold agree — with one caveat.

“I will use it judiciously when needed,” he said, “and drive myself when I can.”