But when the police raided his Hempstead apartment, they allegedly found something even more disturbing: video files of a series of rapes committed across Manhattan.
The first victim was seen being raped and sexually assaulted while unconscious both in her own Gramercy apartment and in McDermott's Murray Hill home, police said.
She was assaulted on at least eight occasions in 2010, they alleged.
The second victim was assaulted five times in McDermott's Upper East Side home in 2013, prosecutors claimed, adding that he "slaps and flicks" the woman to prove she is not awake.
They said the videos showed McDermott fondling both women, inserting an object into one woman's vagina and sodomising the other.
Neither one was aware they had been raped until the videos were discovered, authorities claimed.
"The defendant meticulously recorded each of these actions, and then labeled them on his computer," assistant district attorney Jamie Kleidman told Manhattan Supreme Court on Thursday.
The videos were placed in 'files named things like "unconscious" and the victim's name, a folder marked "undressing" and the victim's name,' Kleidman said.
"[There was] a folder marked "rape" and then videos of him raping the unconscious woman," she added.
Also in the digital folders were hundreds of pieces of child pornography, Kleidman said.
She added that it was 'meticulously marked by age, like "2 years old" and the actions the children are being forced to engage in, such as "daddy and daughter."'
McDermott arrived at the court on Thursday to face the child porn counts, and was arrested on the rape charges. He has pleaded not guilty to all counts.
Kleidman urged the judge to hold him without bail because his family have millions of dollars to their name, and he posed a serious flight risk.
His lawyer denied that, but Judge Mark Dwyer said "a sane person would want to flee the country," and approved Kleidman's request.
McDermott's father, Rick McDermott Jr spent 25 years as the CEO of bond brokerage firm Chapdelaine & Co, which is now known as Chapdelaine Tullett Prebon, LLC.
He most recently worked in medical device sales.