Joshua B. Jeyaretnam was an opposition leader in Singapore who championed greater freedom for Singaporeans and sought the introduction of a Western-style democracy. JBJ, as he was often known, was an acerbic critic of the ruling People’s Action Party (PAP), who repeatedly found himself in court defending libel actions for his comments. During his 37-year career as an opposition politician he paid hundreds of thousands of dollars in defamation damages to PAP leaders. The punitive financial losses would lead him to bankruptcy on more than one occasion and bar him from standing for Parliament.

He was often a solitary voice in a country where protests are restricted by limits on public assembly and a law that allows detention without trial. Government critics also complain of limited access to the media.

Seemingly, however, nothing would silence Jeyaretnam’s virtual lone opposition. When retailers refused to stock his books on Singaporean politics, JBJ would stand on street corners and outside railway stations to sell his publications. He became the first opposition politician to win a Parliamentary seat against the PAP in 1981, in a parliament solely dominated by the party since the country’s independence from Malaysia in 1965.

Joshua Benjamin Jeyaretnam was born in 1926 in Ceylon (now Sri Lanka) during a family visit. An Anglican Christian of Sri Lankan Tamil descent, he was educated at St Andrew’s School in Singapore before training as a lawyer at University College London.

He enjoyed a successful early career as a lawyer and judge, but it was his move into politics that changed his lifestyle, and he struggled to pay mounting debts from damages he lost in high-profile defamation cases. A stubborn, fiery and outspoken critic of authoritarianism in Singapore, he sought an end to the controls on freedom of expression and political activities.

JBJ came to prominence in October 1981 as the Secretary-General of the Workers’ Party — the party he founded — when he ended the PAP’s monopoly of Parliament by winning a by-election. Although this was little threat to the PAP, the Government responded by increasing its control over trade unions and the ownership of the country’s major newspapers.

Jeyaretnam lost his parliamentary seat in November 1986 when he was fined and sentenced to one month in prison. The Supreme Court had upheld a conviction for perjury in connection with a bankruptcy case against the Workers’ Party a few years earlier. Under the country’s Constitution, he was not eligible to stand for parliament for five years.

It was not long before he was in trouble again with the authorities and he was fined by a parliamentary committee for abuse of privilege. The fine was levied after JBJ had made allegations of government interference in the judiciary. Further fines were imposed for alleged contempt of parliament and in October 1987 he was removed from the country’s Law Society register. He successfully appealed against this decision and was reinstated as a practising lawyer when the Judicial Committee of the Privy Council in the UK overturned the decision. Singapore, as a former Crown colony and a Commonwealth member, recognised the Privy Council as its highest court of appeal.

It was during the course of his appeal that his previous convictions were said to have been “fatally flawed” but the Privy Council had no jurisdiction over the court where he had been convicted. Only a presidential pardon would allow Jeyaretnam to re-enter Parliament but this was refused by President Wee Kim Wee in May 1989.

Jeyaretnam’s disqualification from Parliament remained in force until November 1991, which prevented him from standing in the general election three months beforehand. He had avoided bankruptcy in October of that year by paying S$393,000 for legal costs to Lee Kuan Yew, the former Prime Minister and founding leader of Singapore who had served eight terms in office. Lee had won a defamation action against Jeyaretnam over remarks that JBJ had made at an election rally in 1988. Typical of Jeyaretnam’s attitude was a question he asked Lee in a parliamentary committee meeting in 1985: “Aren’t you a bit annoyed because I don’t crawl to you?” In his memoirs, Lee called Jeyaretnam a “sparring partner” who was all “sound and fury”.

JBJ regained a parliamentary seat in 1997 and retained it until 2001, when he left the Workers’ Party. He was declared bankrupt that year, the result of being unable to pay the fine of about S$367,000 in damages for a defamation action brought by Lee, Lee Hsien Loong (Lee’s son and current Prime Minister), Goh Chok Tong (a former Prime Minister) and others.

The Singapore Government argued that the defamation suits were necessary to maintain the integrity of the PAP’s leaders and therefore their ability to command respect in a complex multiracial society where there are four official languages — Malay (the national language), Chinese Mandarin, Tamil and English. Critics of Singapore’s ruling party, however, said that Jeyaretnam’s alleged defamatory comments would not excite comment, let alone legal action, in most other countries.

JBJ was a socialist at heart who believed that the PAP’s policies were for the benefit of a wealthy upper class, leaving a large underclass of poorer citizens. He railed against what he called the “Lee” dynasty, but his repeated clashes with the Government alienated him from many Singaporeans. He cleared his bankruptcy status last year and was preparing to stand for election again for a new party that he had helped to form, the Reform Party, saying that Singapore had been “enslaved” by its rulers.

Over the course of his many legal battles he estimated that he had paid out more than S$1.6 million in damages and court costs. He said he had lost count of the number of times he had been sued — and lost. Earlier this year JBJ told The Straits Times that “all I want to do is to give people a chance to live their own lives . . . and not have everything dictated to them”.

Jeyaretnam was predeceased in 1980 by his wife, Margaret, whom he had met when they were law students in Britain. He is survived by two sons.

Joshua Benjamin Jeyaretnam, politician, was born on January 5, 1926. He died on September 30, 2008, aged 82