On Monday South African businessman Johann Rupert handed over more than 360 title deeds to residents from his hometown of Stellenbosch.The title deeds were secured with money from one of the Rupert family foundations and follows similar projects in Graaff-Reinet and Aberdeen in the Eastern Cape. The beneficiaries are mostly coloured South Africans who, because of apartheid, never owned their own homes.Ownership will change their lives, one elderly woman said at a previous handover earlier this year, because she will now have something to leave to her grandchildren.Johann Rupert (right) in conversation with PowerFM's founder, Given Mkhari, on Tuesday in Johannesburg. The conversation started out blandly, but ended amid fireworks. Graaff-Reinet is also the place where his father, Anton, considered the greatest of Afrikaner industrialists, was born and where his family funds schools, feeding schemes and one of the most successful training centers for the hospitality industry in the country. Associates say he spends in the region of a billion rand a year in projects like these, including on the feeding scheme that provides three daily meals to thousands of people.READ: Rupert's interview provides hard lessons for those willing to take themBut on Tuesday night that all went out of the window during a contentious interview on PowerFM 98.7 in Johannesburg, conducted by the station's Given Mkhari. During the engagement of more than two hours in front of a live audience, Rupert affronted black South Africa by his tone, manner and statements. He was called "arrogant", "racist" and had callers to the radio station railing against the alleged godfather of the so-called "Stellenbosch mafia".The interview was a curious one to begin with. Rupert almost never grants them and is rarely quoted outside of his companies' annual general meetings. He was also stung by the after effects of the campaign against him initiated by Bell Pottinger in 2016 and feels slighted at being cast as the embodiment of "white monopoly capital". This has made him even more reluctant to open himself up to the media, who he by and large distrusts.He is an enigmatic figure. His companies – the investment holding company Remgro and the luxury goods firm Richemont – pay billions in company taxes, while the Government Employees Pension Fund holds more stock in them than the Rupert family itself. He is also believed to be the single highest income tax payer in the country.When he travels he does so on a South African passport, even though it would be easy and convenient to take Swiss citizenship given the amount of time he spends in Geneva and Europe tending to Richemont. His profile pic on WhatsApp is the South African flag and a leaping springbok adorns the wingtips of his company airplane. He maintains friendly ties with some of the most influential players in world finance, like managing director of the International Monetary Fund, Christine Lagarde. Few South Africans arguably carry the same heft as him in the world of international finance. The largest part of the overwhelmingly black audience laughed and enjoyed Rupert's anecdotes and jokes, but comments by Rupert with a racial connotation angered many.And at age 68 the non-executive chairman of both Remgro and Richemont is also starting to consider his legacy as the inheritor of his father's company, his reputation as an international businessman and his position in South African society and business.Tuesday's interview therefore seems to have been an attempt to speak directly to a demographic that he feels has misunderstood him, his family and the role of private capital the most. And PowerFM seemed to have been the perfect fit: young, modern, focused on the black middle-class and sympathetic to the latent anger and frustration of black professionals.If Rupert could manage to put his story across and they responded to him, it would go a long way to dispel the myth of the mafia and exorcise the ghosts of Bell Pottinger, was the approach.The largest part of the audience, overwhelmingly black and well-to-do (the parking lot was brim-full with Range Rover, Mercedes-Benz and BMW vehicles) laughed at Rupert's jokes and anecdotes and remained engaged for the entire 150 minutes.Former first lady Zanele Mbeki sat in the front row next to ex-minister Geraldine Fraser-Moleketi. Businessman Romeo Khumalo was doing the rounds while Mavuso Msimang, the ANC elder who also serves on the Remgro board, had a broad smile on his face. Some presidential advisors and senior government spokespeople were also spotted at the bar.Paul Harris, the former FirstRand CEO, sat next to Ernie Els and his wife, supporting their friend Rupert, while Remgro sent a crack team as backup, including CEO Jannie Durand and executive Pieter Uys, the former Vodacom boss.Before the event Rupert tweeted that he was "petrified", while a friend of his remarked that he was "extremely nervous" before taking the stage. "We're here to support him, he'll be fine, but he's also worried," the friend said.But things weren't fine.Rupert's references to "blacks", and the back-and-forth about it between him and Mkhari, his attempts at light hearted banter about Shangaans and Vendas and his references to "you people" grated. He spoke of BEE as "handouts" saying he would prefer "leg-ups" and dismissing Mkhari's admonishments as that of the "snowflake" generation.But it was his criticism of Mkhari's peers for not having produced leadership that was the cause of most criticism afterwards. Rupert spoke of his parents and how they "saved and studied like crazy". They did not "buy BMWs and hang around at Taboo (a nightclub in Sandton)", he explained, invoking Steve Biko who he said would never have done that. Many in the audience, including those who laughed with him, heard stereotypes of black profligacy preached by the head of a company that was found during the height of Afrikaner nationalism. And it led to three angry questions from the audience. Rupert was visibly prickly after the interview and immediately reached for his phone when Mkhari wrapped up the event by thanking the audience. By then Twitter was ablaze with criticism of the businessman. Rupert rejected the allegations of racism and bristled at the accusations leveled against him, saying under his breath that he'll "never do this again". Afterwards many in the audience mobbed him, queueing to shake his hand, take selfies and waiting to talk to him. He obliged, stopping for chats, hugging some and kissing others and spoke to television news channel eNCA, before he disappeared into the VIP lounge with Mkhari and a select few guests.Immediate reaction was brutal and callers to PowerFM spoke about the need for stronger regulation of the private sector, white monopoly capital and the hegemony of Afrikaner business.ALSO READ: Rupert schooled in the art of talking but not listeningThe outcome was clearly not what Rupert envisaged. He would have wanted to explain to the black middle class who he is, what he has done and why he's done it. And he tried to explain his feelings about nationalism and apartheid, like he did when he appeared in front of the Truth and Reconciliation Commission in 1997.But what many saw and heard was confirmation of the caricature created by the state capture project in 2016 and 2017.And that remains the South African paradox: how to square a person who does good deeds with the same person who says objectionable things.