Starting his journalism career in 1963 as a trainee journalist, he rose to become Editor-in-Chief of SPH's English and Malay Newspapers Division - a position he occupied for 19 years - before retiring in 2006. "I have seen newspapers closed when they fell foul of the government, and friends lose their jobs.... I did not suffer their fate," said Cheong, but wouldn't deign to reveal how he survived being "at the receiving end of Lee Kuan Yew's fury". Mostly likely, he simply moved with the flow, like George Yeo did, instead of sticking out for his journalistic principles. Cheong did confirm though, the "favourite instrument" of changing editorial leadership in newsrooms.
In November 2003, senior staff members of TODAY (Mr Ernest Wong, Group Chief Executive Officer of Mediacorp (publisher), Mr Mano Sabnani (Editor), Mr Rahul Pathak (Deputy Editor) and Ms Val Chua (unfortunate journalist who filed the offending report) were taken to the woodshed to face the full wrath of Lee, for their write-up “SM Lee and the eye opening trauma in London,” which was based on verbatim inputs from the official press release. Warned against "writing any articles that were risqué", the unpalatable paragraphs were never disclosed, but one possibility was quoting him as saying that he had made a phone call to 10 Downing Street asking them to help as his wife had to wait till 6 hours before she could have a brain scan. Which put British Prime Minister Tony Blair in a spot. The upshot was that Lee's press secretary had to issue a follow up statement, "Lee Kuan Yew regrets that he was mistaken that 10 Downing Street had anything to do with his wife getting a CT scan at 3:30 a.m."
It has been said Lee has no compunction about putting journalists on a very short leash when it comes to reporting on his family and the PAP. Only his daughter can write about him asking his bed-ridden wife to change the elastic band in his running shorts. According to Dr Lee's article in the Sunday Times, the feisty woman, who was recovering from a recent stroke and whose vision was impaired, told him: “If you want me to prove my love for you, I will try.” That should sum up Cheong's picture of the press in Singapore, an ongoing love-hate relationship.