I think this is a great moment in world history but those are complex, rambling thoughts perhaps for the future. I would like to draw contrasts to Singapore's political system and political climate for now.
The Obama victory speech:
The McCain concession speech:
Beautiful, gracious speeches. They will have serious difficulties ahead, in practice, trying to work together in the future. However, they publicly offer support for working together. This is a scene sadly seldom seen in Singapore, PAP and opposition alike. Too much bad blood, too many personal dirty-tricks designed to keep people out of politics and too much fear (or paranoia on the part of the PAP).
They also speak of working for "all Americans", not merely for those who voted for them. I contrast this to the sheer arrogance projected by the PAP when they indicated that wards that voted for them gets priority in government projects like HDB upgrading. Goh Chok Tong had even suggested Potong Pasir could turn into a slum if they continued to support Chiam See Tong at one point. If it was political rhetoric, it was poorly played. I shudder to think of a leader who would allow an otherwise ok estate to devolve into a "slum" simply because it's residents had not decided to vote his or her way.
An elected government, in my opinion, is expected to do the right thing and spend resources fairly to solve problems for the nation as a whole (e.g. upgrading estates based on age and disrepair). The PAP government is not such a government.
Obama said in his victory speech:
There will be setbacks and false starts. There are many who wont agree with every decision or policy I make as President, and we know that government cant solve every problem. But I will always be honest with you about the challenges we face. I will listen to you, especially when we disagree.
For most of the time, the PAP takes the opposite "you voted for us, you do what we tell you to do" approach. To be fair, they have often tried to be honest about the challenges Singapore faces (for unpopular policies). However, the refrain has come across mostly been "trust us" rather than "why we believe this policy works and here is the detailed evidence". Officials in Singapore only seem to offer "reasons" that really do not mean much in the context of the problem other than the fact that they make remote sense. The "reasons" offered have always felt more as a means to assuage people than a means to help people understand. Only on rare occasions have they ever grudgingly listened to their constituents when they *disagreed*. The North-East corridor traffic conditions were only acknowledged after Mah Bow Tan took a trip on a peak-hour bus. The Serangoon Gardens worker hostel issue seems to be half-addressed, it was unclear how much of resident-concerns and suggested solutions were considered and a compromise reached.
Maybe some day Singapore can have her Obama-moment. Frankly, I do not see it happening in my lifetime. It scares me how many people believed in the William Ayers rhetoric. If something similar happened in Singapore, I am sure the ruling party would have employed the ISA. Worse, if an election went this way, I am almost certain Lee Kuan Yew would make good on his comment that "the army would have to be called in". At best, Singapore's Obama would come in the form of a PAP candidate if this is even to be possible.