The death of Singapore's founding father marks a milestone in the island-nation's 50-year history and raises questions about what the next decade will bring for the country's political system.
Lee Kuan Yew (LKY) was considered one of Asia's greatest statesmen for turning a fishing village into a first-world economy, but his political ideology made him a controversial figure at home and abroad. His vision centered on a one-party political system, manifested by the People's Action Party (PAP) that he co-founded, which combined elements of capitalism and a state-directed economy.
Strict controls over freedom of speech and censorship are among his more contentious policies, but Mr. Lee's passing should now allow for a more open debate on those issues, Michael Schuman, TIME Magazine's business correspondent for Asia, told CNBC on Monday.
Read MoreLee Kuan Yew's most memorable quotes
"You can make the argument that though LKY had tremendous success, it may be time for a change. He made the case for having a soft authoritarian government…Now, times have changed and I think Singapore will revisit his ideas and say: this worked in the past, but do we need something else going forward in the future. Do we need to have more political and social change? Those are the big questions going forward."
Political opposition in the tiny Southeast Asian city-state is limited to a few names including the Workers Party, the Democratic Progressive Party and The Singaporeans First Party, which was formed last year. Some say that Mr. Lee's policies, like restrictions on public protests, have limited the ability of these parties to grow, but they are still gaining traction. During the 2011 general election, the opposition won a collective 40 percent of the vote.
Going forward, Ernest Bower, senior adviser at the Center for Strategic and International Studies (CSIS), believes the city will shift to a pluralistic political system.
"Singaporeans will harvest the legacy that LKY has given them of an excellent education and global linkages and they will loosen up and create more political space," he said. "Singaporeans will be able to have a more normal governance structure than they have had in the past, so finding consensus rather than implementing the views of a political genius."
"I think there's a genuine, palpable desire for people wanting political plurality. That's been like a genie kept in a bottle, and now the genie is completely out," agreed PN Balji, strategist at RHT Digital & Media and former deputy editor of The Straits Times, alluding to increasingly opinionated social media users as well as several protests last year on issues related to government transparency.
Singapore will hold its next general election sometime before January 2017 and political observers say it will be a real test for the ruling PAP.
Lee's passing may complicate the timing of elections, said Citi analyst Kit Wei Zheng in a note on Tuesday. He believes the vote could be delayed until September, which would be more likely than a May or June poll.
Bower at CSIS expects the opposition, led by the Workers Party, to receive a larger share of the vote this time around, which should see Singapore's political landscape resemble a globally-accepted two-party system where parties compete for ideas.
"I'm telling Washington that, geopolitically, we have to be ready for a Singapore that's less decisive," he said.
This article has been updated since it was originally published following an updated statement from Citigroup.