The summary is not right. Lets all bear in mind that he lost his deposit. Here are my views why he lost.
1) He does not know the meaning of "independent" when was a founding cadre member of the PAP, held the position for over 30 years and well past his retirement.
2) His statements, comments, views etc expressed in public painted him as an imbecile
3) His time in NTUC, the captive market provided for him, the swimming pool on top of the roof etc
4) He exceptionally poor spoken English despite holding a CEO post of a National entity, his poor articulation skills did not lend itself to the office of President
5) Asking for citizens to petition him to stand for PE suggest illusion of grandeur
6) there are probably many more things.
The issue is not TJS, TCB etc, the guy just did not have the gravitas to run a bubble tea shop. Despite being an actuary, if NTUC did not have him I don't think he would have made it. The fact that he attempted to sell batteries online suggest that he does not know what he is doing.
Nothing to do with the cut and thrust of politics, outfoxed or outgunned etc. The guy cannot make it. He was believing in his own bullshit. If you recall his online polls that he conducted where the results showed that he was beating TCB and others hands down. Explain to me how did a trained actuary fail to even secure his deposit?
Summary of the whole story. At a time when PE looked like going to be a walkover, I introduced GMS and Locke to approach TKL to stand. Winning wasn't expected but just adverting another walkover with a good margin to send PAP a good message. TKL as an actuary, harbored no unrealistic expectation too. Of course, that was actuarial calculation behind the scene but in electoral politics, we all had to put a front as contesting to win to get as high a margin as possible.
Then in came TCB who announced that he wanted to stand too. Locke went over to the TCB camp. That was still alright, as a margin of 20 to 30% for TKL was still there since the bulk of the votes TCB was going to split away would be from TT. In fact, there was a high probability that TCB would win leaving TKL a good margin and a good pieces of cream pies on the faces TT and PAP. The whole scenario was disrupted when TJS was unexpectedly given a PE COE too.
The basic hard core no-need-campaigning 20% opposition votes would be split by TJS who had stood under SDP in GE. That's why he said TJS contesting was the "lowest point" in his life. I withdrew from a futile and meaningless campaign by then. GMS carried on with him. TKL as actuary knew that well in his heart. But he's also human and have feelings. He felt he was already in too deep to withdraw. The objective then became to score higher than TJS. He lost, and lost badly.