None of the failures were more heartbreaking than the last time the World Cup was in England in 1999, when Allan Donald's farcical run out and South Africa's last-over collapse in the semifinals against Australia led to a tie and elimination on run rate.
That's the worst of a truly bad bunch, which also includes a rain-affected loss in the semis on the team's debut in 1992, an embarrassing run-rate miscalculation and group stage elimination on home soil in 2003, and a surprise defeat to New Zealand, again in the semis, four years ago.
So, how to heal the mental scars? Because even young players, uninvolved in those losses, have felt the pain. "This is something I've watched teams do," says batsman Rassie van der Dussen, one of the newcomers to the squad. "You think about South Africa and World Cups, there's probably more negative memories than positives."
Previous South African teams decided not to speak about the failures as if ignoring them would help them go away. They haven't. Twenty years later, South Africans still ruminate on the Donald run out. Appearing on a talk show last year, Donald explained how he dealt with it.
"I had to get rid of that ... and so I made a point of watching that thing (the run out) over and over and over again. Not because I wanted to beat myself up for it. It's just I wanted to watch it and make peace with it really."
The 2019 squad, led by coach Ottis Gibson and captain Faf du Plessis, has taken a little of that on board. Both say the players have discussed the disappointments and the mental pressure that comes with trying to overcome them. Because even if the South Africans don't want to think about them, the media and opposition will bring them up at the World Cup, du Plessis says.
"Whether you're young or old, when you get to the tournament that's going to be there, that's a fact," du Plessis says. "For me, the thing now is making players aware of it and giving them ways of understanding it, of dealing with it."
South Africa has five players appearing at their third World Cup: Du Plessis, fellow batsmen Hashim Amla, and JP Duminy, and bowlers Dale Steyn and Imran Tahir. This will likely be their last chance to win it.
There's also a new crop, three of whom — batsman Aiden Markram, allrounder Andile Phehlukwayo, and fast bowler Kagiso Rabada — can claim World Cup success for South Africa. They all won the 2014 Under-19 World Cup.
"It's a new adventure for us," says Gibson, who coaches South Africa at the World Cup for the first time. "We've got a couple of guys who have been to World Cups before but we've got a lot of guys, it's their first one and we want to make it special for them. But, again, we don't want to put too much emphasis or too much pressure on the fact that it's a World Cup.
"We're not building it up to be anything other than what it is. It's still cricket." Gibson's previous job as England bowling coach will undoubtedly be an advantage in assessing conditions. South Africa also isn't weighed down by the favorites tag. That's England, which South Africa plays in the opening game on May 30.
The biggest concern, away from the mental state, is the fitness of two key fast bowlers. Steyn and Rabada both came home early from the IPL, Steyn with a flare up of a problematic right shoulder injury and Rabada with back issues. South Africa's bowling, with pacers Steyn, Rabada and Lungi Ngidi, and legspinner Imran Tahir, is its strength.
Amla, du Plessis, Quinton de Kock, and David Miller are all top 50-over batsmen and the 24-year-old Markram, who nearly didn't make the squad, could be the wild card. It depends on if the previous World Cup pain can be put to good use.
"We're wounded buffalos, I reckon, and that's when we're at our most dangerous," allrounder Chris Morris says.
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