Firstly just to clarify, Lee Kuan Yew was Singapore’s Prime Minister, and while we do have a President as head of state, the real political power lies in the hands of the head of government, i.e. the prime minister.

Lee Kuan Yew was one of the founding fathers of the People’s Action Party, Singapore’s largest political party that has attained a supermajority in parliament since winning its general election in 1955 until the present day (2022).

There are a few ways to determine “free and fair” elections. As for electoral processes, Singapore has had a relatively good track record of elections being free of corruption. Freedom House states that “Elections are largely free of fraud or other irregularities”. So at least at face value, Singaporean elections are not directly rigged in favour of the PAP, despite their consistent supermajorities in parliament.

However, it is accepted and known that the PAP government under Lee Kuan Yew, especially in the 1960s and 70s have taken rather heavy handed measures to ensure that the opposition parties are weak and that their own public perception remains strong and positive. This is where the “levers of government power” come into play.

There are frequent gerrymandering of constituency borders. In fact, it's quite funny that our own state media has openly admitted and produced a tool for citizens to check how many times their house has changed constituency. (https://www.straitstimes.com/multimedia/graphics/2020/06/singapore-general-election-ge2020-constituency-changes/index.html)

The constituency system itself is full of controversy. The establishment of GRCs (Group Representative Constituencies) in 1988 require a party to designate up to 5 candidates, with at least one of a minority race, and if majority votes for a political party is achieved, the “winner takes all”, meaning all seats in the GRC are given to the winning party, regardless of the proportion of votes. It is thus more difficult for the opposition parties to field enough people to contest the multiple constituencies, to the extent that it is common to have many constituencies be “walkovers”, the reason for which will be explained below.

Singapore requires all nominees to deposit a sum equal to 8% of the total allowances payable to an MP in the calendar year preceding the election, rounded to the nearest S$500. In 2020, this sum was S$13,500 and if you receive less than ⅛ of the total number of votes, the deposit is forfeited. Economically, opposition political parties are disadvantaged since they will have to fork out a lot of money to put up candidates to contest seats.

Many members of the opposition would also be frequently sued for defamation by the PAP, namely Mr Joshua Benjamin Jeyaretnam, leader of the largest opposition party in Singapore, Workers’ Party, in 1988, 1995 and 1997, declaring bankruptcy in 2001.

Although the situation seems quite grim for Singapore’s political atmosphere, credit where credit is due, the Singapore economy and the standard of living for Singapore has improved significantly and is one of the best in the region and dare I say in the world under the PAP government and under Lee Kuan Yew’s leadership. In that regard, their popularity is well deserved and their continued good reputation of a lack of corruption and continued economic prosperity in Singapore is a major contributing factor to their streak of electoral victories.

So both sides of the coin positively reinforce each other. The people favour the PAP due to their historical successes and at the same time are indirectly discouraged from supporting the opposition as they are rendered “weak” and many prefer stability under a tried and tested government. Singapore’s society has become a lot more politically apathetic as a result of the many systems put into place as explained above.