"He was crying. I don’t understand him at all. On one hand, he worked so hard for merger. Having gotten the cupful, he shattered it. And then cried over it.
He held two successive press conferences, and in which both he cried. On the third morning I went to work, and saw the press boys again. I asked Lee Wei Ching, his press secretary, “Why are they hanging around here?” Another press conference! I told Lee Wei Ching, “You ought to tell the Prime Minister to go to Changi and take a rest. Call the press conference off! Another crying bout, and the people of Singapore will think the government is on its knees."
British declassified document:
""He emphasised seriousness of the occasion and threatened "punitive" measures against any newspaper which printed pictures of him smiling."
Goh Keng Swee:
Melanie Chew: When did you feel that Malaysia was going to break up? Was it a surprise to you?Dr Goh: Now I am going to let you into what has been a state secret up to now. This is a file, which I call Albatross.
In the early days there were a lot of discussions about changing the terms of Malaysia by the Prime Minister, Rajaratnam, and Toh Chin Chye. It got nowhere. They discussed all types of projects. Was Singapore to be part of Malaysia, but with special powers, or with no connection with Malaysia?Now on the 20th of July 1965, I met Tun Razak and Dr Ismail. Now this is the 20th July 1965. I persuaded him that the only way out was for Singapore to secede, completely.
(reading) “It should be done quickly, and before we get more involved in the Solidarity Convention.” As you know, Rajaratnam and Toh Chin Chye were involved in the Solidarity Convention. “Malaysia for the Malaysians,” that was the cry, right?
Melanie Chew: This Solidarity Convention, you felt, would be very dangerous?
Dr Goh: No, not dangerous. I said, “You want to get Singapore out, and it must be done very quickly. And very quietly, and presented as a fait accompli.”
It must be kept away from the British. The British had their own policy. They wanted us to be inside Malaysia. And, they would have never agreed to Singapore leaving Malaysia. Now, the details, I won’t discuss with you.
Melanie Chew: How did Tun Razak and Dr Ismail react?
Dr Goh: Oh, they themselves were in agreement with the idea [of Dr Goh’s proposal to get Singapore out quickly]. In fact, they had themselves come to the conclusion that Singapore must get out. The question was, how to get Singapore out?...
Melanie Chew: What was his view? Did he himself want Singapore out?
Dr Goh: I had better not say.
Melanie Chew: So the secession of Singapore was well planned by you and Tun Razak! It was not foisted on Singapore!
Dr Goh: No, it was not.
(There followed a long silence during which he slowly leafed through the secret file, Albatross. Then he shut the file, and resumed his narrative.)
--- Leaders Of Singapore / Melanie Chew
Addendum: Also, via Secret documents reveal extent of negotiations for Separation: Lee and friends were "excited" about independence, looked at it as "an escape" and called it "most attractive", and looked forward to "political stability with economic expansion, and autonomy in Singapore without interference from KL" - all this a few (?) months before independence. Since Singapore's independence from Malaysia had been discussed for over half a year, it being presented as sudden and a fait accompli just testifies to the success of the PR campaign.
All these add on to Tunku Abdul Rahman's account ("I don't know why Mr Lee acted like that . . . He was quite pleased about it"), which corroborates the claim that the crying was staged.
Addendum: Related - Toh Chin Chye - "He was crying. I don't understand him at all."