After he unsuccessfully stood for the
House of Commons at
Streatham as a Liberal Party parliamentary candidate in 1959, aged 21, he joined the Liverpool Shoe Company, founded by his parents, Berko and Minnie Rubin, immigrants from eastern Europe. He was joint managing director with his father for 10 years until his father's death in 1969, when he took the role of chairman. owning a number of brands including
Berghaus, Brasher, Ellesse, Hunter,
Mitre and
Speedo, amongst others. It is also the majority owner of
JD Sports Fashion plc. Its success largely came from an investment in August 1981, acquiring 55% of
Reebok for 77,500. By 1983/84, Reebok accounted for 70% of Pentland's turnover. Pentland's shares rose from 55p at the start of 1984 to 3 at the end of the year and up to 10 in 1985, while profits rose from 1 million in 1983 to 12.9 million in 1985. Rubin then sold off Pentland's stake in Reebok for 770m in 1991. The following year he was named second on the same list, having paid £143.9m in tax. In February 2026, Stephen Rubin was listed on the Sunday Times Tax list with an estimated £325.6 million. ==Honours and awards==