CNN
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Days after the husband of missing Massachusetts mother Ana Walshe was arrested on a charge of misleading investigators, details of his tumultuous legal history are beginning to emerge.

The mother of three was reported missing by her coworkers on January 4, but a sweeping two-day search of the small coastal town of Cohasset, Massachusetts, turned up no sign of her.

Her husband, Brian Walshe, told police he last saw his wife on New Year’s Day, but investigators allege he provided them a false timeline of his actions and whereabouts around the time she disappeared. He has pleaded not guilty to the charge of misleading investigators.

And Brian Walshe’s previous legal battles have provided insights into how people close to his family have characterized him before his wife’s disappearance.

The 47-year-old husband has previously been described by relatives and family friends as an angry and dishonest person, according to affidavits filed during a 2019 legal dispute over his father’s estate.

“Brian is not a trustworthy person,” wrote Jeffrey Ornstein, who said in the affidavit that he was a close friend of the father and had previously shared an apartment with Brian Walshe. Ornstein also claimed Brian Walshe’s legal statements in the case were “based on lies and misrepresentations.”

CNN has reached out to current and previous attorneys for Brian Walshe but has not heard back.

Additionally, Brian Walshe is awaiting sentencing in a prior federal fraud case in which he was accused of selling fake Andy Warhol paintings online, according to court documents.

As investigators continue to dig into Ana Walshe’s disappearance, possible evidence has been uncovered, including bloodstains and a damaged, bloody knife in the family’s basement, prosecutors have said.

Her husband’s internet records included searches related to how to dismember and dispose of a body, according to law enforcement sources, and a hacksaw and apparent bloodstains were found while searching a trash collection site, law enforcement sources said.

Law enforcement sources also told CNN they expect to have the district attorney empanel a grand jury to begin hearing witnesses, reviewing videos and issuing subpoenas for records.

When Brian Walshe unsuccessfully contested his father’s will in 2019, his father’s nephew and two close friends submitted affidavits attempting to discredit Walshe’s claims.

His father, Dr. Thomas Walshe, who headed the neurology division at Brigham and Women’s Hospital in Boston for over a decade, died in 2018 in India, according to the documents.

Dr. Walshe bequeathed to Brian only his “best wishes” and “nothing else” from his estate, noting that he was no longer in contact with his son, according to photographs of the will included in court documents.

However, Brian Walshe objected in an affidavit in November 2019, arguing that he was “one of only two legal heirs” to his father’s estate. He said his father’s health had been “very poor” when he signed what Brian described as a “suspect” will, and he suggested his father’s signature on the document was a “possible forgery.”

In their affidavits rejecting those claims, his father’s nephew and friends detail years of alleged swindling and manipulation by Brian Walshe.

“My Uncle’s Last Will and Testament confirms what he had told many people over the years that he did not want his son, Brian, to inherit anything from his Estate,” wrote Andrew Walshe, the estate’s executor and one of Dr. Walshe’s nephews, in an affidavit.

Ornstein wrote that Dr. Walshe told him Brian had been “diagnosed as a sociopath” and had been a long-term patient at a psychiatric treatment facility in Massachusetts.

Brian Walshe is “a very angry and physically violent person,” Dr. Fred Pescatore, who said he was a longtime friend of Dr. Walshe, wrote in his affidavit, noting the estrangement between father and son was due to “Brian being a sociopath.”

In his affidavit, Brian Walshe claimed that he and his father had been estranged over the years but had “reconnected” in 2015 and began “speaking regularly” in 2016. He also claimed the two properties tied up in the estate had an estimated value of over $1 million.

Separately, Brian Walshe was indicted on federal fraud charges in 2018 for allegedly selling fake Andy Warhol artwork on eBay, according to court documents.

He allegedly took real paintings from a friend to sell, but never did, according to the documents. He did not compensate the friend for the art either, prosecutors alleged.

Last year, he pleaded guilty to wire fraud, interstate transportation for a scheme to defraud, possession of converted goods and unlawful monetary transaction, according to the Justice Department.

In a letter to the federal judge hearing the case, Walshe said he was “extremely sorry” for his past conduct and promised he had changed since the crime was committed. Ana Walshe also wrote a letter to the court that she was grateful he was able to remain under house arrest during case proceedings.

Norfolk District Attorney Michael Morrissey said Tuesday that police were searching areas north of Boston on Monday in the “suspicious disappearance” of Ana Walshe.

“A number of items” were collected in the searches and were sent for testing, the district attorney said in a statement. He declined to provide details on the items.

Law enforcement sources told CNN Tuesday that investigators sifting through trash at a Peabody, Massachusetts, transfer station found materials that may be related to the case, including a hacksaw, torn-up cloth material and what appears to be bloodstains.

Crime scene tape was also placed around dumpsters in an apartment complex near the home of Brian Walshe’s mother in Swampscott, about 15 miles north of Boston, the source told CNN. Brian Walshe told police he went to visit his mother on January 1, the day he told police he last saw his wife, according to the affidavit.

But police allege many of the statements Brian Walshe made to investigators were “untruthful.”

Brian Walshe told investigators he last saw his wife the morning of January 1, when she said she needed to fly to Washington, DC, for a work emergency, according to an affidavit from police.

However, investigators found no evidence that his wife took her usual rideshare to the airport or got on a flight that day. Her phone also pinged near the house on January 1 and 2, according to commonwealth prosecutor Lynn Beland.

Brian Walshe is under home confinement as he awaits sentencing in his prior fraud case and must get permission to leave the house at specific times, and for specific locations and reasons, according to police.

He made multiple unapproved trips the week of his wife’s disappearance, according to the affidavit, including to a Home Depot where he was seen on surveillance video wearing a surgical mask and surgical gloves and making a cash purchase. In court Monday, prosecutors alleged he spent about $450 on cleaning supplies, including mops, a bucket and tarps.

Law enforcement sources told CNN that investigators hope to collect blood samples from the couple’s sons so they have a “direct bloodline” sample to compare against traces of blood found in the couple’s basement.

Brian Walshe is being held on a $500,000 bail and is set to appear back in court on February 9.