Anne Arundel County Executive John Leopold faced trial in January on charges of misconduct in office for using his security detail to transport him to mall parking lots to have sex in his car. (Astrid Riecken/The Washington Post)

How sorry is John Leopold?

The answer is likely to be key at Thursday’s sentencing of the former Anne Arundel county executive, who was convicted of misconduct in January after a salacious trial that delved into parking-lot trysts and catheter bags.

Leopold stepped down as county executive shortly after the trial. His attorneys argue that his resignation and the damage to his reputation are significant enough punishment and proof that he is contrite.

Prosecutors are less sure. They noted in a sentencing memo to Anne Arundel Circuit Court Judge Dennis Sweeney that they were not aware that Leopold has “ever expressed remorse for his outrageous and illegal actions” and that they won’t be satisfied until he does.

Under normal circumstances, said Emmet Davitt and Thomas McDonough of the state Office of Special Prosecutor, they would have sought jail time. But they were not recommending it in this case because of Leopold’s age and health issues. Leopold turned 70 in February and had two back operations in 2010. He still uses a catheter, his attorneys told the judge in court filings.

Davitt and McDonough have recommended a one-year suspended prison sentence, a $100,000 fine, 500 hours of community service and five years of probation.

Leopold’s attorneys, Bruce Marcus and Robert Bonsib, are pushing for probation only, citing the absence of a previous criminal history and the Republican’s long record of public service.

The final decision will rest with Sweeney, who found Leopold guilty of abusing his authority by having his security detail and staff perform personal and political errands, including collecting campaign contribution checks. Sweeney singled out the treatment of his scheduler Patricia Medlin, who had to empty her boss’s catheter bag for months, as “predatory and cruel” and said his actions smacked of an “overbearing arrogance and sense of entitlement that is unworthy of someone who is suppose to be a public servant.”

Leopold was cleared of other misconduct charges, stemming from his use of his protection officers to ferry him to sexual encounters in a bowling alley parking lot and to keep his live-in girlfriend and his mistress apart while he was hospitalized in 2010.

The girlfriend, Jane Miller, sent a letter to the judge, and it was combative as well as contrite on Leopold’s behalf.

“Dealing with his infidelity has been extremely difficult and personal,” she wrote. “I know he is remorseful and contrite, and that continuing our relationship is very important to him.”

Miller then launched into an attack on his accusers, especially Medlin. She wrote that the scheduler was always willing to help Leopold with his health issues before the trial and often looked up symptoms and conditions for him on the Internet.

“We called her Dr. Patti,” Miller wrote. She also noted that Medlin, who testified that she feared for her job if she refused to do as Leopold asked, “had no problem being assertive when it came to scheduling her six weeks of paid vacation.”

Miller also drained Leopold’s catheter bag and said it was “not a big deal.”

“It is sad that the help given by his staff has been misconstrued so that it appears he was in some way abusing his power,” Miller wrote. “This was certainly not his intent and he is sad and sorry if it appeared that way. He had no idea they were offended.”