The private jet headed for Macau with a full crew and three women from China.
Now, the man, who works with a local aviation company, is facing accusations that he took the joyride in May last year without the owner's permission.
The company he works for, based at Seletar Airport, manages the aircraft for the owner - a listed company.
A source familiar with the listed company said this is not first time the manager has done so.
The source said that in November 2012, the manager took another of the listed company's planes without its permission. The general declaration, or passenger list, revealed the senior manager had boarded the private jet with another passenger.
The plane landed at Johor's Senai Airport and picked up two more passengers - both senior executives with another aviation company here - and flew to Australia.
As far as the aviation rules go, the manager did not break any aviation laws.
He had followed all the proper procedures, including filling up flight plans for the trips. But the company which owns the US-registered jets, worth around $49.2 million, has now taken them away.
Another company, based in Australia, has now revealed that it too had problems with the senior manager's company.
The Australia-based company has "grounded" its jet following an internal probe. This was revealed by the chief executive officer of an overseas airline. The airline is the registered operator of the private jet.
The CEO, who declined to be named, told The New Paper: "Our concerns regarding the company's practices relate to our opinion that they have committed substantial safety and security breaches."
He refused to elaborate, but added his airline had severed business ties with the local aviation company early this year.
Some in the aviation industry had heard of the joyride episodes.
Said one local aviation company operator, who refused to be named: "The industry is a small one, so we hear about these things.
"If anything had happened during those unapproved flights, there would be no insurance cover and of course the pilot could lose his licence."
The three passengers on the November 2012 ride declined to comment.
TNP tried last week to speak to the man accused of organising the joyrides but his secretary either said "he was not in" or that "he was busy".
TNP understands the senior manager has foreign criminal convictions including theft and causing a disturbance.
Did he break any laws with the joyrides? No, said Mr Ravi Madavaram, an aerospace and defence practice consultant with Frost & Sullivan: "This seems more like a legal battle than an aviation safety or security issue. It would have come under our scope if they flew without telling the airport. If the owners didn't know, then it's not a safety breach, but rather a company internal policy (issue)." Mr Liew Hui Sing, from Singapore Polytechnic (SP), said the answer was not so clear cut.
Said Mr Liew, 39, the course chair for SP's aeronautical engineering department: "I feel it's a very grey area. In terms of the aviation industry's point of view, nothing was breached.
"There was no air crash or aircraft damage. They (the aviation company) followed the proper flight paths... (which) is all part of the basic rules and regulation in the industry. But, like borrowing a car, it's common courtesy to inform the owner first."
Lawyer S Balamurugan disagrees, especially in the wake of the disappearance of Malaysian Airlines Flight MH370.
He said: "This is not a bus ride to Tekka (Market). Surely, it's a security issue because the owner has not authorised the aviation manager to fly overseas. If the jets mysteriously disappear, the owner will be in trouble."
This article was published on April 7 in The New Paper.
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