A rich-lister's manager said his boss was happy to bleed cash if it resulted in an indecent assault allegation disappearing, a court has heard.
And a secret recording at an Auckland bar has also revealed the pair seemingly joked about sending the alleged victim to Turkey to be killed.
He is also charged with twice trying to pervert the course of justice by offering a bribe for the 2016 complainant - the first of the three to go to police - to drop their claim.
The businessman denies the charges and has claimed he is the victim of blackmailing efforts.
One of the alleged attempts to dissuade the witness, included a meeting between two public relations consultants and the complainant at the five-star Palazzo Versace hotel on the Gold Coast in May 2017.
The Crown alleges the PR workers were hired by the businessman through his manager, who is also on trial for attempting to pervert the course of justice.
However, the alleged "Gold Coast plot" failed and the complainant told police about the approach.
Within 24 hours of returning to Auckland, the two PR workers met the businessman's manager at Family Bar on Karangahape Rd. Their discussions were recorded by one of the consultants, which has been played to the jury today and yesterday.
The PR consultants have temporary name suppression and have both been granted immunity from prosecution by the Solicitor-General in exchange for their evidence for the Crown.
One of the consultants, who has political connections, can be heard on the Family Bar recording raising the possibility of intimidating the complainant.
The businessman's manager agreed and said: "Yeah, because it sounds to me if it was a reasonable person with a real kind of comprehensive hold on reality, you could make an offer that's reasonable and they would accept."
He also later mentions, seemingly jokingly, a discussion he had with the businessman about sending the complainant to Turkey to have him killed in a "traffic accident".
The PR consultant also mentioned he knew a friend who could help arrange "a deal or put him in a body bag", the court heard.
"No, I'm not joking, no, I'm not joking," the consultant said.
The manager said the rich-lister appeared concerned about his legacy, the lack of a deal, and the prospect of spending more money on alleged attempts to dissuade the complainant.
"The only thing that pisses him off and makes him get cold feet is when he feels like it's a slippery slope and it won't get a resolution," the manager said.
"So because he got burnt by [a well-known entertainer] and because this first mission didn't succeed, [the businessman] is going to be very hard to convince on my part to get into this ... he's going to say 'and here we go again, first we lost that much dosh and now we've lost this much dosh'.
"He's happy to bleed if it gets resolved ... But he's thinking it's never getting resolved ... and we're going to end up in court with everyone knowing."
The PR consultant also suggested leaving the entertainer out of any future plans, while the manager called him a "snake" with dollar signs in his eyes.
"I ain't going down for this sh*t," the PR worker said.
The entertainer has already pleaded guilty to two charges of attempting to pervert the course of justice for trying to have the 2016 complainant drop their allegations, including the Gold Coast attempt and an earlier effort in April 2017.
He has name suppression and is due to be sentenced next month.
The first PR consultant told the court today he knew what he was doing was "wrong and potentially criminal".
"We all left ourselves exposed, frankly, and we were all involved."
The High Court trial in Auckland continues on Monday.