Chiam's political longevity is rare in Singapore, whose ruling People's Action Party juggernaut has for decades eclipsed the weak and inexperienced opposition, which usually campaigns for more political freedom in the tightly controlled city-state.
Today, Chiam, 71, is one of two opposition members who hold seats among 84 elected positions in Parliament.
At recent campaign rallies, former Prime Minister Goh Chok Tong has questioned whether Chiam has the stamina to run his constituency for another term.
But Chiam, a lean, bespectacled man with neatly combed salt-and-pepper hair, says that age is not an issue and that he has proven he can help constituents without ruling-party connections.
Lee, 82, was Singapore's founding prime minister and still wields political clout as a senior Cabinet minister.
Lee transformed Singapore from an impoverished former British colony into one of Asia's richest, most stable societies.
But Lee and other PAP leaders have sued opposition politicians, several of whom have seen their careers sidelined after they lost the lawsuits, were unable to pay damages and went bankrupt, disqualifying them from running for office.
But Chiam has earned respect as a serious politician whose willingness to work hard within the system contrasts with other opposition figures. PAP leaders have generally spared him the worst of their criticism and legal action.
Chiam's Potong Pasir constituency is Singapore's smallest, with just 15,864 voters.
But the PAP is taking Chiam seriously enough to send Goh - a popular, affable, longtime leader - to try to help swing Potong Pasir's vote in favor of the PAP's candidate Sitoh Yi Pin, 42.
Chiam, a retired lawyer, first won a parliamentary seat in 1984 and has held it for five consecutive terms, but voter support dipped to just over 52 percent in the last election in 2001, the AP reports.
Potong Pasir lacks many amenities found in PAP-represented communities, such as glitzy shopping malls, cinemas, supermarkets and libraries. But Chiam's supporters say this gives it a laid-back charm.
Renovations for public housing - home to nearly 90 percent of Singapore's 4.2 million people - will give priority to constituencies that vote for the ruling party, the government says.
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