Before betting emerged from the back streets in 1963, the industry the young Cyril joined was dustily archaic. Clerks protected the privacy of clients behind curtains, entering bets with quill pens into huge ledgers. It was rumoured that nothing short of an entry in Debrett would secure credit.
Using the cash flow from racing to fund its expansion into hotels, do-it-yourself and property, Ladbroke was always driven by the single-minded determination of one of British business's most secretive characters.
Mr Stein is better known for eschewing an entry in Who's Who than many are for having one, and is widely described as aloof and offhand.
He guards his family's privacy as vigorously as he raises funds for Israel. He was not available yesterday because of the imminent arrival of the Sabbath.
Not that his image has always been so saintly. In 1979 many felt that Ladbroke was heading into oblivion after its casino licences were taken away. Mr Stein describes it as his lowest point.
Other lukewarm fans include the horsey set, distinctly underwhelmed by the disparity between the money Ladbroke takes out of racing and what it puts back.
Whatever Cyril Stein is, he is the personification of Ladbroke. It came as no surprise to anyone close to the company that he finally realised he was unable to hand over the reins.