A little more than 10 years ago, Generoso “Jerry” Capodilupo, after a decade as a substitute teacher in Boston public schools, began contemplating a holy life.

A lifelong Catholic and the son of a painter with work on display at the Vatican, Capodilupo entered into what Catholics call “discernment”: visiting religious orders to see if he could devote himself to Jesus Christ.

Capodilupo spent time with priests and monks in Massachusetts, New Jersey, Hawaii and Washington, D.C. By 2010, he said he was far enough along to call himself a monk on his Facebook page, which lists his employer as God.

“As a MONK, someone who has renounced the world and all its vainities [sic], this is somewhat different than usual,” Capodilupo wrote in his first Facebook post on May 16, 2010. “This is all new to me. I will go slow. I am not too sure I really want to come out and be part of this insane world.”

But as the years went by, Capodilupo’s thousands of Facebook posts, written under the name “Jerry Lupo,” began to veer from meditations on his faith to conspiracy theories, anti-Semitic rants and screeds against religious communities he accused of rejecting him.

Now, Capodilupo, 60, is accused of taking his opinions from the Internet to the real world. He sits in D.C. Jail facing multiple counts of defacing public or private property after allegedly writing anti-Semitic graffiti in Chinatown in separate incidents last month.

Police say Capodilupo wrote the word “Jew” on an image of the Chinese zodiac rat on a crosswalk at Seventh and H streets NW. In two other incidents, he allegedly drew swastikas on windows and tables of a Starbucks in Chinatown, as well as at another Starbucks at Seventh and E streets NW.

Henry Escoto, Capodilupo’s attorney, said his client denies the allegations against him.

“We’re challenging the government on their evidence,” Escoto said.

It’s not clear what brought Capodilupo to Washington. But according to public records, interviews with priests he met and his Facebook posts, he has spent more than a decade traveling from city to city, searching for some sort of religious community. In between, there were a couple of arrests and convictions for trespassing, including one last year in Arlington. A restraining order was issued against Capodilupo in Hawaii in 2011.

Capodilupo was born in Boston, where his father was a real estate broker and artist. One of his paintings was displayed at the Vatican.

He became estranged from his family after attending Suffolk University in Boston and getting involved with drugs, according to his brother, Luciano Capodilupo.

“The family have tried back years ago to assist as much as possible,” said Luciano Capodilupo, who added that he hadn’t seen his younger brother in at least 10 years. “We still love him, but there’s nothing we can do because he has to do it himself.”

Luciano Capodilupo said his brother taught public school in Boston and eventually moved to Hawaii, where he married.

Capodilupo’s pretrial services report indicates he is married, though no record of a marriage could be found in public records.

His Facebook page occasionally refers to his time as a teacher — “I got in trouble with the filthy radical zionist jews and freemasons back in 2002 when i taught my Boston School pupils about the Genocide,” he wrote on May 26.

A spokesman for Boston public schools said Capodilupo resigned his position there in 2004 to relocate to another state.

Sometime after that, Capodilupo spent time at the Missionaries of the Sacred Heart of Jesus and Mary, a religious community of priests and monks in Linwood, N.J., but he did not take vows there.

Father David Lupo of the Congregation of the Sacred Hearts of Jesus and Mary said he met Capodilupo in Massachusetts around 2005.

“He was just a little odd, that’s why we didn’t take him,” Lupo said, adding that they turned him down “for vitriol against the Sacred Heart community.”

Capodilupo would later excoriate the priest on Facebook.

“This priest is clueless, selfish and useless,” Capodilupo wrote. “I told him that he was a dead beat Catholic Priest.” It’s not clear when Capodilupo landed in Hawaii, but in 2010 he began talking about his island home in Facebook posts, commenting on its beauty and “light trade-winds.”

“I’m a teacher, artist (I love michaelangelo and Salvador Dali) psychologist and trained and experienced psychotherapist,” he wrote from a Starbucks. “I’m writing a book on my spiritual journey and experiences along the way. I wish [to] compare and contrast Mental Health and Illness in relationship to psychology, relegion and society.”

The coffee shop Capodilupo wrote from on the North Shore of Oahu was about 10 miles from the Benedictine Monastery of Hawaii, where staff said he attempted to join the order.

Father David Barfknecht, the order’s prior, said he remembered Capodilupo as an intelligent, homeless man who may have been struggling with mental illness.

“Jerry is an interesting case,” Barfknecht said. “But just trying to connect his own perception of things to how other people perceive things is probably a challenge.”

Barfknecht said Capodilupo spent about two weeks there as he contemplated joining. He was living in a cave on the beach “trying to be like Jesus,” Barfknecht said.

His application proved unsuccessful.

“He just wasn’t manageable in the sense of taking direction, taking guidance,” the prior said. “It wasn’t because of particular violence or hate speech.”

According to Capodilupo’s Facebook page, he arrived in the Washington region in late 2014.

Father Christopher Wyvill of St. Anselm’s Abbey in Northeast Washington said Capodilupo visited the abbey in March of this year.

Wyvill said Capodilupo initially approached him for help writing a book, and stayed for a meal and evening prayers. But Capodilupo’s talk of conspiracy theories was a red flag for the abbey’s residents, as was a YouTube video he forwarded to Wyvill comparing Jesuits with “war criminals.”

“He did not stay here, as far as I know,” Wyvill said.

Wyvill soon became the focus of one of Capodilupo’s posts.

“After talking with Fr. Chris of the Benedictine Order at St. Anslems here in Washington D.C. DID I FIND OUT AND REALIZE ONCE AGAIN THAT SOMEONE SAID SOMETHING TO HIM THAT LED HIM TO HAVE A VERY PREJUDICIAL NEGATIVE ATTITUDE,” he wrote on April 2. “Very not Christian.”

Capodilupo, whose next court appearance is Friday, has not written on his Facebook page since June 16, when he called Pope Francis “the Antichrist.”

But a month earlier, he offered a gentler message, quoting “Auguries of Innocence” by Romantic poet and religious visionary William Blake. The poem mixes visions of heaven with stark images of hell.

“To see the world in a grain of sand /­ and heaven in a wild flower / hold infinity in the palm of your hand / and [eternity] in an hour,” Capodilupo wrote.

Peter Hermann contributed to this report.