ANNAPOLIS, Md. (AP) — Before he developed a long-running grudge against The Capital Gazette, the man who police say opened fire and killed five newspaper staffers directed his anger at a female high school classmate he barely knew.

Courthouses in Maryland are clogged with lawsuits brought by Jarrod Ramos against judges, reporters and lawyers he thought had wronged him. In each case, they took the side of the classmate who said Ramos had harassed her relentlessly for a year.

Ramos, 38, of Laurel, Maryland has been charged with five counts of murder in Thursday’s shooting — one of the deadliest attacks on journalists in U.S. history.

Court documents and social media posts written by Ramos paint a portrait of an angry, frustrated man fuming about how he’d been mistreated and maligned.

His aunt, Vielka Ramos, said her nephew was highly intelligent, but was a solitary man.

Ramos grew up in Severn, about 20 miles from Annapolis, and attended Arundel High School, graduating in 1997.

In late 2009 or early 2010, Ramos contacted a former high school classmate via email thanking her “for being the only person that was ever nice, or said hello to him in high school,” the woman wrote in court documents when she sought a peace order protecting her from Ramos in January 2011.

She said Ramos told her about mental health issues he’d been having, so she suggested a clinic. Ramos then sent her a series of hateful and vulgar emails, including calling her a “dirty slut,” she wrote.

She eventually went to police, and Ramos ended up pleading guilty to a misdemeanor harassment charge. Five days after his guilty plea, the newspaper wrote a story about the case.

Ramos filed a defamation lawsuit, but a judge dismissed the case, finding that Ramos could not point to a single statement in the article that was false. But Ramos, acting as his own attorney, pursued the case all the way up to Maryland’s highest court, the Court of Appeals, which denied his petition in 2016.

In his written court filings, Ramos frequently used overwrought language. In 2012, when the newspaper argued to have the case tossed out, Ramos referred to his complaint as “a blob of facts — fed and grown on their own sins — and they have stepped right in it, to be eaten alive.”

In one court document, Ramos refers to himself as a citizen who “values truth, integrity, equal justice under the law and fair access to the courts.”

After his lawsuit against the newspaper was dismissed, Ramos posted profanity-laced tweets about the paper, its reporters and editors.

Ramos’ online grudge seemed to disappear for a while until some new posts appeared just before the killings.