Even before he earned national infamy for jacking up the price of life-saving cancer and HIV meds and then being a general shit about it on Twitter, Turing Pharmaceuticals CEO Martin Shkreli was working hard on a toxic reputation. Court documents show Shkreli’s disturbing history of tormenting the wife and daughters of a business foe.

Timothy Pierotti was a colleague of Shkreli at his pervious biotech venture, Retrophin, before an alleged business deal gone awry created bad blood. From there, legal documents allege, Shkreli proceeded to harass and threaten Pierotti’s family via email, Facebook, LinkedIn, and text message. Pierotti says Shkreli—a one time Forbes “30 Under 30” honoree—even broke into various online accounts owned by his family:

In January of 2013, Pierotti’s wife received this letter, ostensibly from Shkreli, in which he says “I hope to see you and your four children homeless and will do whatever I can to assure this”:

The campaign of harassment continued through the rest of 2013, including a litany of Facebook messages and friend requests, including one sent to Pierotti’s elderly father. A sampling can be viewed below:

Pierotti’s son, 16 at the time, received these IMs:

Shkreli was even creative enough to use LinkedIn as a channel for harassment:

The creepiest moment from a creep who seems to know no bounds is this text message to Pierotti’s wife—one of many such “sweetie” texts, according to a police report:

That same police report includes accusations that Shkreli had broken into Pierotti’s Gmail account, using that access to reset his Facebook, LinkedIn, and Twitter accounts. Shkreli allegedly went so far as to publish unflattering posts about Pierotti from Pierotti’s own Facebook account, prompting him to discover that many of his passwords had been changed without his permission:

According to the police report, Shkreli denied even knowing Pierotti when contacted by an officer. He later settled out of court for an undisclosed amount, Bloomberg reports.

You can read the full legal complaint below: