Arrigo Sacchi has hit out at Harry Kane and Tottenham, claiming the England captain does not have a 'great personality' and that Spurs are not trophy contenders.
Jose Mourinho's men are currently languishing in ninth place in the Premier League, six points behind the Champions League places, despite Kane's 13 goals and 11 assists in the top-flight this term.
But legendary coach Sacchi, widely regarded as one of the best managers of all time, does not believe Kane has the character to match his talent.
When asked to analyse England captain Kane, Sacchi suggested that the Spurs talisman's leadership skills could be partly to blame for their lack of silverware.
'He is definitely a great footballer, but I'm not sure if he has a great personality,' Sacch told Sportsmail.
'It doesn't seem to me that Tottenham has ever been a protagonist to win'.
Jose Mourinho's side were top of the Premier League towards the end of November but have suffered a major slump in form and now face an uphill battle to finish in a European spot come the end of the season.
Spurs have, however, managed to reach April's Carabao Cup final and will take on Pep Guardiola's Manchester City in the final.
Sacchi, who won back-to-back European Cups with AC Milan and guided Italy to the 1994 World Cup final, also claims English football has come a long from being out-of-date to one of the best leagues in the world.
The Italian added: 'The Premier League is the most interesting championship. The best coaches in Europe are there. English football wasn't up to date.
'But now it's right on top thanks to Guardiola, (Jurgen) Klopp, Mourinho and (Carlo) Ancelotti's hard work.
'In the past, English football was quite opinionated and therefore did not keep up with the times and thus continued to do that they always used to. But I am convinced that very soon there will also be English coaches.
'I have seen huge improvements in the English youth teams, while the senior national team has room for improvement.'
Sacchi also highlighted the work done by Marcelo Bielsa's in Leeds' first Premier League campaign in 16 years.
Bielsa's side have received plenty of plaudits since their Premier League return and are on course to establish their place in England's top-flight for next season.
When asked which Premier League side he enjoys the most, Sacchi replied: 'The Leeds coached by Bielsa plays an enjoyable and courageous game.
'Innovation and courage are children of knowledge. Without knowledge there can be neither innovation nor courage.
'English football has always been courageous, the only thing missing is that it's never been updated.'