Dr Chee Soon Juan has been gaoled more than a dozen times for challenging Singapore's restrictions on free speech and political activity.
Dr Chee is also the leader of the Singapore Demcracy Party and currently a visiting fellow at Sydney University's Democracy Network.
And while he says times are changing in his home town, some constructive criticism would help.
Correspondent: Karon Snowdon
Speakers: Tony Abbott, Prime Minister of Australia; Dr Tony Tan, President of Singapore; Dr Chee Soon Juan, leader, Singapore Democratic Party
SNOWDON: There are two prominent Singaporeans in Australia now. One of them was welcomed by Prime Minister Tony Abbott.
ABBOTT: It's a real thrill to have you here.
SNOWDON: Singapore's head of state, President Tony Tan Keng Yam has held the largely ceremonial position since 2011. Previously, an appointment of the Parliament, the presidency has been subject to a popular vote since 1991, a major political development.
TAN: Relations between Australia and Singapore are very close and are becoming even more inter-connected due to our coommon interests and our shared world view.
SNOWDON: Chee Soon Juan is currently a visiting Fellow at Sydney University's Democracy Network. Dr Chee is also the leader of the Singapore Democratic Party, a controversial figure who's been jailed numerous times for flaunting Singapore's laws against holding rallies without a permit.
He has been sued for defamation - a regular tactic to quell dissent, by former Prime Ministers Goh Chok Tong and Lee Kuan Yew and was declared bankrupt, since annulled, for refusing to pay damages. He says while Singapore and Australia are close allies their politics are quite different.
CHEE: We still are not a democratic state.
SNOWDON: Singapore has been ruled by the People's Action Party since 1959.
The island is prosperous and has a regional presence far beyond its size. Its people have tended to accept the status quo and the rule of a political elite in exchange for stability and economic well-being, but that might be showing signs of strain.
A new opposition party emerged last month. And recently six thousand people rallied in support of a blogger being sued by the Prime Minister Lee Hsein Loong.
The Democratic Party, the SDP has been around for 34 years, increasingly challenging the PAP's stranglehold on politics and free speech. It claims to have an expanding membership among young people, but currently has no sitting members in parliament.
Dr Chee says social media is allowing people to exchange ideas and organise in a nation where mass media is state-controlled.
CHEE: In the past year or so, we've had many many events where Singaporeans have shown great dissatisfaction about the way things are being conducted.
SNOWDON: Do you think there's a case for a friend like Australia to raise these issues in Singapore about the restrictive nature of the media and government if indeed as is constantly said our relationship is based on a shared world view?
CHEE: If Australia really wants to engage Singapore in a more meaningful, more substantive manner, then I think the question of whether the people of Singapore - how their aspirations are going to be met in a democratic state, then I think that must come into play at some point.
SNOWDON: Australia and Singapore have one of the closest bilateral economic, political and security relationships in South East Asia. Singapore has been invited to attend the G-20 summit in Brisbane as a guest later this year. And Tony Abbott is comfortable with the status quo.
ABBOTT: I'm very conscious of the fact that we have your military personnel at airforce base Pearce at Oakey. I'm conscious of the fact that we exercise together regularly and I really am very keen to see ever closer bonds between Australia and Singapore. It's a very strong friendship.