Ties to Russian crime gangs
Now she's accused of obtaining fake IDs — including a US passport and several drivers' licences — and is being investigated by the FBI for her role as president of a charity called the United Hearts of Mercy.
Founded in Canada by Florida-based Russian businessman Valery Tarasenko, the charity claimed to be a non-profit helping children in need. However, it is believed to be a front for Russian organised crime gangs.
The story was broken by The Pittsburgh Post-Gazette, who sent emails to more than two dozen charity donors in Hong Kong, all of which bounced back — suggesting they were fake email addresses.
Ms Yaschushyn has also been tied to a condo development under investigation in Canada, however Quebec police are yet to release more information as to why.
Bad blood between charity workers
In a separate issue, Ms Yashchyshyn and Mr Tarasenko are currently caught up in a lawsuit in which she is claiming that the Russian set her by producing multiple fake IDs without her knowledge.
In a deposition, she said, "Every single move that I did, I've been told by Valeriy to do so... [a]fter a few incidents like that, I realised that he's using me for his lifestyle and for his needs."
In another affidavit, she stated that when she tried to leave him, he repeatedly hit her.
"Over time, Tarasenko became more controlling and aggressive over me," she said.
While Mr Tarasenko has talked with the FBI, it's unclear if he is also facing an official police probe.
For his part, he claimed their relationship was simply that she babysat his children while he was away on business.
He said their relationship broke down when he discovered she had abused one of his children — a claim she denies.
He's also claiming that she was very keen to work her way into Mar-a-Lago to find rich benefactors.
Security concerns
The ease with which Ms Yashchyshyn was able to gain access to Mar-a-Lago — the epicentre of Republican Party politics — has authorities concerned over security breaches, particularly in light of the recent FBI raid which uncovered classified and top-secret materials that Trump had taken from the White House.
The Secret Service — whose job it is to run security for current and former presidents — told The Pittsburgh Post-Gazette it couldn't comment on whether the agency is investigating Yashchyshyn's visits to the former president's home.
"To maintain the operational integrity of our work, we are unable to comment specifically concerning the means, methods or resources used to conduct our protective operations," said Steven Kopek, a special agent and spokesman, in a statement.
