The controversial Sun International CEO SleepOut event last night raised over R30 million for education charities.
Meanwhile, Twitter users said the event made fun of the plight of the homeless and that it was a glorified slumber party for rich people.
More than 200 business leaders, including some from the South African tech and telecoms industries, took part in the challenge.
Nelson Mandela Bridge was cordoned off for some of SA's richest leaders to experience sleeping on the streets in the middle of winter.
The evening's proceedings were delayed by protestors in Braamfontein. News reports indicate tear gas and rubber bullets were used by the police to disrupt the protest action. It is unclear if the protest was against the SleepOut or another issue.
Once the CEOs started to fill the bridge, there were stalls made to look like corrugated iron 'shacks' that offered the business leaders hot soup, coffee, extra blankets, boxes to sleep on and the password to the free WiFi.
All sleeping bags, boxes and leftover food were to be donated to actual homeless people after the event.
The participants could also bring clothes to be donated to the less fortunate. The clothes were hung on rails that hugged the edges of the bridges, keeping some of the cold out, and the smoke from makeshift fires in.
The CEO SleepOut Web site explains: "While this does not begin to simulate the reality of South Africa's most vulnerable children, it is a show of solidarity and a commitment to use business as a force for change."
Biggest charity event
Last year, the event raised over R26 million for Girls & Boys Town and was the largest sum raised by a single South African charity event.
This year, the event raised over R30 million. The beneficiaries this time will be Asha Trust, Columbia Leadership and the Steve Biko Foundation.
The organisation decided to focus on education initiatives this year instead of charities that dealt directly with homeless people, the rationale of which was that education may prevent future generations become homeless.
Last night, the CEOs were joined by a staff member from their organisation, a student and a matric learner. Each CEO and their team were required to commit to raising R160 000.
Brett Levy, co-CEO of Blue Label Telecoms, for the second year in a row was the CEO to raise the most money for the event. Last year, he raised R380 000, and last night, his total was over R570 000.
He said this feat was largely due to the people that backed him.
Responding to the social media criticism of the event, he said: "You can never feel what homeless people do, of course not, but this gives you a little taste of it for one little evening and we get to do it along with South Africans and we do it in good spirit. I think that's what is important.
"The truth is richer people will never feel what homeless people do and I don't think tonight is about that... it is about raising money and getting out [there].
"The fact that rich people don't stay in their homes and just donate the money to a bank account and actually physically come out and do it, I think that says a lot," said Levy.
Jon Ayache, Uber SA GM, echoed this sentiment: "I think it is a fantastic initiative. It is very easy to forget when we are sleeping at home in our beds what many, many people in South Africa have to face every day."
MTN SA CEO Mteto Nyati said the event was more about awareness and spreading empathy among SA's richest.
"Most of the time, we are so busy running our lives, chasing deals, doing this and that, we end up being blind to some of the problems in front of us.
"However, initiatives like this make us as CEOs ask ourselves how we can contribute to make the world a more equal place."
Twitter push back
During the event last night, social media platforms were aflutter with people who were strongly in favour or strongly against the event.
Those against it said if the CEOs really wanted to give back, they should do so without making such a fanfare out of it and closing off key access points to the city.
Tshepo Motsepe tweeted: "The homeless who sleep on Mandela Bridge will tonight have their shelter back, without police protection, free WiFi and coffee."
Obakeng Leseyane said: "Sometimes people have great intentions. But the execution of those intentions sends forth a different message."
In response to the mudslinging, Emma Turd tweeted: "I'm not happy about #CEOSleepout2016 but I'm going to donate money to charity rather than whine about it on social media" followed by the hashtag #SaidNooneEver.
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