In 1960, Checkers was a tiny chain of five supermarkets, a speck in South Africa’s retail landscape. By 1965, it had exploded to 85 stores, thanks to Raymond Ackerman’s vision. That’s the dawn of Checkers’ success story—a saga of grit, customer obsession, and bold moves. But the tale doesn’t end there.
After Ackerman’s exit, Checkers faltered, only to be resurrected in 1991 by Whitey Basson and Shoprite, who turned a bleeding giant into a cornerstone of Africa’s biggest retailer. This isn’t just history. It’s a masterclass in building, losing, and reclaiming success. Let’s dive in—first with Ackerman, then Basson—and uncover lessons you can wield today.
The Birth of Checkers Under Ackerman
Raymond Ackerman didn’t invent Checkers, but he birthed its soul. Raised in a retail family—his father Gus founded Ackermans in 1916—he learned early that value wins customers. At the University of Cape Town, studying commerce, he met W.H. Hutt, who drilled “consumer sovereignty” into him: the customer rules. It shaped him. After graduating, he joined Ackermans in 1951, greeting shoppers at the door. Simple work, sure, but it taught him their pulse.
Fast forward to 1960. Greatermans, having bought Ackermans, gave Ackerman a shot at managing small-town stores. Self-service supermarkets were buzzing in America, and Greatermans tested one in Springs. Ackerman assisted—and loved it. He saw the future: food retailing, fast and affordable. So he pitched Checkers—a dedicated supermarket chain. In 1956, the first store opened in Mayfair, Johannesburg. It was small, scrappy, and the start of something big.
Stumbles, Learning, and a Breakthrough
Those early stores? They tanked. Mayfair, Germiston—failures all around. The Greatermans board shrugged. Ackerman didn’t. He knew the issue: no one understood supermarkets. South Africa wasn’t ready. He begged to study in America. After a fight, they relented. With wife Wendy, he spent six months there in the early 1960s, not observing but working—butchering meat, stocking shelves, pricing goods. He met Bernardo Trujillo, who preached customer-first as smart business. Ackerman returned a changed man.
Back home, he faced pushback. Greatermans saw Checkers as a department store appendage. Ackerman saw a supermarket empire. He got to work anyway. From 1960 to 1965, he scaled Checkers from 5 to 85 stores. His playbook? Low prices, fresh stock, and layouts that clicked with shoppers. By 1965, Checkers outshone Greatermans itself, becoming South Africa’s top supermarket group. Success, though, stirred envy.
The Fall—Ackerman’s Exit
The board didn’t cheer—they bristled. Ackerman told the Sunday Times jealousy festered. Tensions peaked in 1966. At 35, he faced a room of execs from OK Bazaars, Woolworths, and Spar, pushing price fixing. He refused. It was illegal, yes, but also against his core—customer trust. Three days later, Greatermans’ chairman, Norman Herber, sacked him. Weeks after his father’s death, it stung deep. Checkers lost its spark. Ackerman? He bought Pick n Pay from Jack Goldin for R620,000, starting anew. Checkers drifted, a giant without a guide.
Checkers’ Limbo Years
Post-Ackerman, Checkers didn’t collapse—it just stagnated. Greatermans milked its 85 stores, but the vision faded. By the late 1980s, it was bleeding cash. Five CEOs in eight years couldn’t stop the rot. Losses hit R45 million annually by 1991—a fortune then. Checkers was upmarket, yes, but directionless. Enter Whitey Basson, Shoprite’s wunderkind, who saw not a corpse but a prize.
Checkers’ Success Story Reborn
Basson’s story starts earlier. In 1979, he’d bought Shoprite—eight stores, R1 million—from the Rogut family under Pepkor’s wing. With Christo Wiese’s backing, he grew it fast, snagging distressed chains. By 1991, Shoprite had 241 stores, but Basson wanted more. Checkers was his target—ripe to reignite Checkers’ success story. Raymond Ackerman, now at Pick n Pay, loomed as a rival bidder. Basson moved quicker. With Wiese and Sanlam’s Marinus Daling, he engineered a R55 million reverse merger. Shoprite swallowed Checkers.
The catch? Checkers was a mess—losing R45 million yearly. Investors panicked, slashing Shoprite’s stock 60% in three months. Basson didn’t flinch. Nine months later, Checkers was profitable. How? He slashed costs, centralized distribution via Sentra (bought same period), and kept Checkers upmarket while Shoprite hit the masses. By 1998, after snagging OK Bazaars for R1, Shoprite’s turnover leapt to R14.6 billion—eclipsing Pick n Pay’s R10.97 billion. Checkers, rebranded as Shoprite-Checkers, became the jewel.
Checkers Evolves Under Shoprite
Basson segmented smartly. Shoprite took LSM 4–7; Checkers aimed higher, LSM 8–10. By 2003, he launched Usave for LSM 1–5, but Checkers stayed premium. Four years repositioned it against Pick n Pay and Woolworths. Freshmark (2000) streamlined produce; LiquorShop (2005) added booze. By 2016, Shoprite hit R130 billion in revenue, Checkers a key driver. Basson retired that year, passing Pieter Engelbrecht a titan. Checkers FreshX (2017) and Sixty60 (2019) cemented its edge—upmarket, innovative, fast.
Checkers After Basson: A New Chapter
Whitey Basson stepped down in December 2016, pocketing a R1 billion handshake after 38 years. Pieter Engelbrecht, a 17-year Shoprite veteran, took the helm. Checkers didn’t stall—it surged. Engelbrecht doubled down on its premium edge. In 2017, he launched Checkers FreshX—big, sleek stores with sushi belts, wine cellars, and artisanal breads, targeting affluent LSM 8–10 shoppers. Over 68 opened by 2023, stealing share from Woolworths. Customers loved it—think restaurant-quality steak while grabbing groceries!
Then came Sixty60 in November 2019. A game-changer. Checkers deliveries in 60 minutes, R35 flat fee. The app? Downloaded 3.1 million times, serving 400+ locations by 2022. Sales jumped 250% in one period, then 87% more to December 2022. Engelbrecht partnered with RTT Group, forming Pingo Delivery (50% Shoprite-owned), boosting tech and reach. Checkers Xtra Savings, launched 2019, signed 5 million users in six months—1 million in 72 hours! By 2019, Shoprite ranked 86th globally among retailers, Checkers a linchpin in its R131.65 billion market cap. Engelbrecht’s vision? Affordable, accessible, innovative. Checkers thrives on it.
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Lessons From Two Titans
Checkers’ success story spans decades, two leaders, one truth: adaptability wins. Ackerman built it on customer love—85 stores in five years proves it. Basson saved it with scale and smarts, turning red ink black in nine months. For you? Focus on your customer like Ackerman—know them, serve them. Learn hands-on; his U.S. grind paid off. Bounce back—fired, he thrived. From Basson, master acquisitions: spot value in chaos, act fast. Cut waste, segment markets, innovate late (FreshX!). Checkers stands tall today—over 3152 Shoprite stores, 152,000 jobs—because two men dared. What’s your move?
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