On November 25, 2014, "Bulletproof" was firing big shots in Key's direction. Using a Facebook account under his real name, he commented on a story about the then 19-year-old making his DJ debut.
"At least it would be a great opportunity to lock the basement door shut and pour flammable liquids under it, casually flicking a match you used to light your cigarette into a puddle that will become a fiery death for said fashion and gastronomic elitists," Monds wrote.
This evening, the Herald approached Monds though George FM's parent company, MediaWorks, for comment about the 2014 post.
In a written statement provided through a communications staffer, he did not offer an apology to his new employee.
"I'm pretty sure that back then, I was just as biased towards Max as everyone who is now against his appointment to a resident [spot] on George FM," Monds said.
"But, like everyone passionate about their craft, he's a lot better after time and practice and Tuesday nights 10-11pm on GeorgeFM will show that."
Key's new role at the station - hosting a one-hour show on Tuesday nights - was unveiled last week. His first show will be this Tuesday, when he will unveil his new single, Forget You, rumoured to be about his recent split from Amelia Finlayson.
An unverified email reportedly sent to all George FM staff warned them that "all social media" relating to the new George FM night-time hosts "must be positive", and Monds has been on the front foot fighting Key's corner over the past few days.
"The decision to bring Max on board for George Nights was mine and mine alone," he posted on Facebook through his "Jay Bulletproof" account.
"I also hold my close friends' opinions in high regard. When I trust someone, I trust them implicitly. So when a couple of those friends brought up Max's name as an 'emerging talent' in New Zealand dance music, I wasn't even skeptical, especially having spent 5 days with him at Spring Break Fiji.
"I finally met him in person and was humbled by his own humility, and it wasn't long before I realized he's just a bloody good kid."