A decisive figure in Singaporean politics, Chee was arrested and jailed several times for his unconventional political activities, mainly for making unauthorised public speeches as well as staging demonstrations without a police permit. He was also found guilty of defamation on multiple occasions for comments he has made about members of the country's governing People's Action Party (PAP). He was previously barred from standing in parliamentary elections because he was declared bankrupt in 2006, after failing to pay damages from a lawsuit owed to two former prime ministers, Lee Kuan Yew and Goh Chok Tong.