Tottenham could have done with Tim Sherwood's levels of persuasion on these occasions.
Kane has since gone on to sensationally score 29 goals in all competitions and earn an England call-up, and Sherwood's comments did not really sit that well among Spurs fans, with the ex-boss seen as trying to take credit for his emergence.
But what if Sherwood was right, and it was all down to his persuasion? We have taken a look at five Tottenham deals from recent years where he had he had the platform, he should have stepped in to prevent...
When Spurs signed Roberto Soldado it seemed like a sensible decision at the time, after all he had been prolific in La Liga for three consecutive seasons. It clearly has not worked out though, he has scored just one Premier League goal this season and four in all competitions. Vetoing the decision to sign him from Valencia could have saved Spurs £30 million.
Selling Gareth Bale
If anyone could have convinced Gareth Bale to snub Real Madrid, it's Tim Sherwood right? Bale had his heart set on a move to La Liga, but he is experiencing a tough second season after a promising first. He was poor in the recent El Clasico, and having him to link up with Harry Kane is a dream partnership for Spurs had they managed to keep hold of him.
A former England international, Bentley turned out to be a terrible signing for Tottenham. They spent £15 million on buying him from Blackburn, and beyond an impressive goal against Arsenal, he contributed very little. After struggling to find a club after being released he landed up retiring, claiming he had fallen out of love with the game.
Had Tottenham managed to keep Berbatov, who knows what would have happened? After he forced a move to Manchester United in 2008, Juande Ramos' team fell apart. The sale destabilised them, and Ramos was sacked eight games into the season without a win, and the Harry Redknapp era began.
If only Sherwood had been at Spurs in 2005. He could have helped convince Martin Jol not to shell out on Derby County striker Grzegorz Rasiak. He made only eight appearances for Spurs, and did not score a single goal. A career in the Championship beckoned, and the Pole was never able to prove what all the fuss was about.