Tomorrow Jeanne Clarke Harris is expected to plead guilty in U.S. District Court to campaign corruption charges. It will not be her first time at the rodeo.

A couple of decades ago, Harris was sentenced in federal court to two years’ probation and given a $10,000 fine for hiding knowledge of allegedly criminal acts involving the misuse of city money by former Ward 7 Councilmember H.R. Crawford, according to published accounts from that time.

When asked if she’d learned a lesson from her ordeal, Harris replied: “Yes, be careful,” according to a 1989 article from The Washington Post (which is not available online; LL found it in Nexis).

It’s fair to wonder if Harris followed her own advice. Harris is at the center of a wide-ranging federal investigation into Mayor Vince Gray‘s 2010 mayoral campaign, including an off-the-books “shadow campaign.” A long-time public relations professional and associate of Jeff Thompson, Harris saw her house raided by federal authorities earlier this year. Tomorrow, she’s expected to plead guilty to soliciting her friends and family to be straw donors—i.e., to give money they were later reimbursed for in order to get around limits on individual contributions—and to impeding investigators looking into the matter. Her attorney, Fred Cooke Jr., didn’t immediately respond to LL’s request for comment.

Harris, her companies, her relatives who live in Georgia, and entities connected to her companies are a large part of Thompson’s network of donors who give to the same politicians at the same time, almost always at the maximum amount, campaign records show. In the last ten years, LL counts more than $80,000 in local political donations from entities with ties to Harris, with some donations coming in the form of money orders. Much of the recent scrutiny over Thompson-linked donations has centered on his habit of giving large amounts of cash through money orders. One of the biggest recipients of Thompson money, Councilmember Vincent Orange, has called the money orders he’s received from Thompson questionable and suspicious because many have sequential tracking numbers.

Harris has long enjoyed strong ties to those in power in District government. Currently, her nephew, Warren Graves, has one of the most important and powerful perches in city government, as City Administrator Allen Lew‘s chief of staff. Harris was tapped to plan former Mayor Anthony Williams‘ 1998 inaugural gala. And before her guilty plea in 1988, Harris’s public relations firm used to have several city contracts and employed Effi Barry, the late wife of then-Mayor Marion Barry.

Published reports from the late ’80s detail how Harris pleaded guilty to concealing two “criminal schemes.” One involved funneling money to one of Crawford’s aides (who was sentenced to six months in prison). The other involved adding one of Harris’ employees to Crawford’s council payroll as a way of paying for newsletters her firm had produced for Crawford, who was not charged with any wrongdoing. Court records say Ivanhoe Donaldson, a former top aide to Barry who was sent to prison for stealing city funds, played a role in one of the schemes, according to a Post story.

At her sentencing 24 years ago, Harris’ lawyer said she’d been shunned by the city’s political class for cooperating with authorities in their probe of Crawford. Harris said the months after her guilty plea were “very painful, very lonely, but I’m looking forward to starting my life again.”