After McDonald was evicted, the owner of the house found that he had caused about $1.3 million worth of damage to the property, including smashing the oven and sliding glass doors and breaking three toilets, according to the FBI.
In July 2025, McDonald was charged in Woburn District Court with breaking into the home and causing more than $1,200 in additional damage, including punching a “smiley face,” into the drywall, a picture of which he sent to the three investors. Activity in that case has been suspended, court records show.
After they cut ties with McDonald, the investors told the FBI they began receiving hundreds of harassing and taunting emails from him on a daily basis over the next few years.
Around April, these messages began escalating from taunts to violent threats, according to the FBI’s report.
“The two year grace period is over, if we cannot come to an accord for my house … [I] would have no problem shooting you right in the [expletive] head,” McDonald allegedly wrote in an April 20 email to the group. One of the investors took out a harassment prevention order against McDonald the next day in Hingham District Court, records show.
That person, the VC partner who was the first to raise alarms about McDonald’s business dealings, hired a security detail and installed cameras at his house shortly after, according to the FBI.
After the partner’s lawyer notified McDonald of the prevention order against him, McDonald allegedly began including him in the violent threats, records show.
The partner reported he began “living in fear,” not letting his children play outside and having his company remove all of its signage at the office, the FBI report said. In a prior email, McDonald had allegedly edited a photo of the partner’s face with a speech bubble reading “Kidnap his kids!”
He also told police McDonald was apparently holding him responsible for the Winchester eviction. In a group of May emails that were reported as violations of the prevention order, McDonald allegedly said that “if I don’t go home one of you is getting shot,” and “it’s my house or your head.”
The other investors said the partner is on the verge of a mental breakdown from the stress, the FBI affidavit said.
Another investor, who owned the Winchester house and had originally planned to sell it to McDonald for Waev stock down the line, had already obtained a restraining order after McDonald allegedly broke into his property in July 2025, records show.
He told the FBI that McDonald’s nonstop threats against him and his son had caused him “severe emotional distress.”
The third investor said that McDonald incessantly taunted him about the death of his adult child, according to the FBI.
In May, McDonald allegedly sent various threatening emails to the group, consistently referring to them as “boomers.”
“I’ll corrupt all the relationships in your life and then kill your son too … how much pain do you want ?,” he wrote on May 2, adding on May 6 that he would tear one of the men apart “limb by limb.”
“Want to know what happened the last time i said someone was going to get shot…?,” he allegedly wrote on May 11. “They got shot 10 times. I can show you the article,” he said.
On May 30, McDonald allegedly wrote that “I’d just rather kill you than make a company.”
On May 6, McDonald was arrested by transit police in Cambridge and charged with felony assault and battery after he threatened a man who stopped an MBTA bus with a knife, court records show.
McDonald’s alleged threats continued during June and July, records show. Between Hingham and Brookline district courts, he has nine pending cases against him for harassment, making threats, and violating a prevention order.
After failing to appear for a court date in his assault case in June, he was taken into custody on Tuesday, records show. A lawyer representing McDonald in that case did not return a call on Friday.
Bryan Hecht can be reached at bryan.hecht@globe.com. Follow him on Instagram @bhechtjournalism.
