Leopold nodded agreeably when a pair of longtime supporters bemoaned a planned town house development, offered sage advice to a mother on how to effectively advocate for a school construction project, and with a trademark dose of self-promotion, boasted about not taking a pay raise.
"We're a well-oiled machine," Leopold said as he left. "This investigation has been going on for a year and government hasn't missed a beat. And we'll continue to do so."
Constituent service has always been Leopold's bread and butter, and has for the past several years helped him overcome persistent questions, accusations and rumors about his personal life. But this latest scandal could be the toughest test yet.
Leopold is banking on his record to pull him through — even as some have called for him to resign. Facing criminal charges, Leopold is sticking to a familiar formula of relentless campaigning and community outreach that has forged his decades-long career in Maryland politics.
As his political career took off in Maryland, so did rumors about his personal behavior. The whispers increased in 2009 when someone called 911 to report sexual activity in Leopold's county car in an Annapolis mall parking lot, but nothing was ever proved. He's also been accused by a state worker of aggressively pursuing her in a lunch line, a complaint that he has said was ultimately dismissed. And a pending lawsuit by a fired county worker alleges a hostile work environment. He has denied any wrongdoing.
In a 2011 radio interview — just weeks after word of the pending criminal investigation leaked — he joked about his early political ambitions and his attraction as a young boy to an elementary school instructor.
"When I was in second grade, I had two ambitions," Leopold told WYPR's Dan Rodricks, also a Baltimore Sun columnist. "One was to be the class president, the other was to have this attraction for my second grade teacher. I achieved one of my goals. I was elected class president."
Long before Leopold hit the Maryland political scene, he made a name for himself in Hawaii. After graduating in 1964 with an English degree from Hamilton College in Clinton, N.Y., he worked for U.S. Sen. Hugh Scott, a Pennsylvania Republican, whose office was decorated with Chinese art.
Intrigued, Leopold took an intensive Mandarin course at Seton Hall University. He moved to Hawaii, hoping to better put his fledgling language skills to use and to be with his then-girlfriend, a Miss China pageant winner who was the daughter of his professor.
He worked as a high school teacher and lived in a rooming house in Honolulu for $80 a month. He made a run in 1968 for the State Board of Education, which only required candidates to have lived in the state for one year. He fashioned a simple sign that read: "Leopold, Board of Education, Have a nice day," and stood on the side of the road.
He won, becoming the board's first Republican and, at 24, the youngest person in statewide office. He married his first wife, Maureen Lahy, an outspoken feminist, in 1969. Leopold was later elected to the state House of Representatives — during that time he worked as the state director of Planned Parenthood — and then the state Senate.
In 1978, he married his second wife, Diane Erbe, and won the GOP endorsement for governor. He lost to incumbent Democrat George R. Ariyoshi, though he drew 45 percent of the vote.
His relations with some in the GOP grew strained. In 1980, a Senate leader said in a letter to party members that Leopold had reneged on a deal and couldn't be trusted. That same year he lost badly in an effort to regain his seat. The following year, he moved to Maryland with his third wife, Leslie Peterson, a speech pathologist from Denver. He never had any children.
He said he grew tired of long monthly flights to Washington after having been appointed by President Gerald Ford to a national education panel, and was eager to get back to the East Coast.
Richard Borreca, a long-time political reporter and columnist for the Honolulu Star-Advertiser said Leopold was "extremely ambitious" given that he was a newcomer running as a Republican in an overwhelmingly Democratic state.
"He always pushed to have himself promoted," said Borreca. "After he left and went to the mainland … John continued to send press releases back to Hawaii, including one on how he managed to secure some native Hawaiian geese called Nene for the zoo in Baltimore."
In Anne Arundel County, Leopold followed his same formula of determined sign-waving and door-knocking. He won election in 1983 to the Maryland House of Delegates and served there until 1990 and then from 1995 to 2006.