Maradona was 33 when Tottenham considered bringing him to north London. His football credentials were beyond dispute: a 1986 World Cup winner who had starred for Boca Juniors, Barcelona, Napoli and Sevilla.
The timing, however, was difficult. His career was increasingly shaped by disciplinary and personal controversies. He had served a 15-month suspension after failing a doping test at Napoli and was expelled from the 1994 World Cup after testing positive for ephedrine.
Sheringham’s recollection is that Tottenham’s concern was not Maradona’s ability. It was the wider risk attached to signing one of football’s most famous and unpredictable figures.
The alternative was Klinsmann, who joined Tottenham from Monaco for £2 million in 1994. His arrival was not universally welcomed, with some supporters remembering his role in Germany’s victory over England at the 1990 World Cup and accusing him of exaggerating fouls.
His response came on the pitch. Klinsmann scored 20 league goals in his first Tottenham season, won the Football Writers’ Association Player of the Year award and was selected in the Professional Footballers’ Association team of the season.
His first spell lasted only one campaign before a move to Bayern Munich, but he later returned on loan in 1997-98. The impact was immediate enough to make him one of the defining foreign players in Tottenham’s modern history.
The Maradona counterfactual will always fascinate Tottenham supporters, but Klinsmann provided the more reliable outcome. The next time Spurs are linked with a superstar whose brilliance comes with serious baggage, this forgotten decision will offer an instructive benchmark.