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20th September 2017
07:56pm BST
He also worked with Harry Kane at youth level and in the first-team. Kane flourished under Sherwood's successor Mauricio Pochettino, becoming one of the best strikers in the world. He's only 24, but the England international has already scored over 100 goals for Spurs.
However, Sherwood reckons if the they don't win a trophy this year, he could leave the club.
"There's only so much loyalty someone can show," Sherwood said on The Debate on Tuesday night.
"Tottenham have been a great club for Harry and he's been paying them back tenfold. He's been outstanding over the last couple of seasons, he grew up a stone's throw from the ground and the kid loves the club. But that only lasts a certain amount of time. Then he starts seeing the pound signs and sees the likes of Barcelona, Real Madrid or - dare I say it - Manchester United - and then your head gets turned. The only way they can keep him is to win something this year. That something might not be the Carabao Cup, it might have to be the league or the FA Cup."
Ian Wright was alongside Sherwood on the show, and he made some interesting points. The former Arsenal striker said that Kane, who signed a contract worth a potential £120,000 a week, is paid less than his market value, but Spurs are unlikely to pay the wages on offer at other clubs.
"What they don't want to do is get Kane into a position where he's got no choice but to kick on, simply because that's what he wants to do," wright said.
"We've seen him do interviews where he says he wants to play in the Champions League regularly and be winning it, and win the Ballon d'Or. He's a very ambitious player. If Daniel Levy isn't going to throw that kind of money their way... and I don't want it to seem to be all about money but it does massively help. When you've got someone like Kane who has two Golden Boots in three years and he's still £120,000 to £150,000 behind somebody, that just doesn't add up. It doesn't make sense and if I was in his shoes, then I would be loyal to Spurs right now, but you cannot tell me that people are not in his ear. He's probably under pressure all the time simply because of what he is capable of earning right now."
Wright does have a point. It may not only be about money, but it is astounding to think there are several players with less than half the talent of Kane being paid more than the striker.
As Ken Early pointed out in The Irish Times, Spurs can afford to pay their players more than they currently do.
However, it was Sherwood's comments that caught the attention of his former club, particularly the view that Kane could leave the club if they fail to win a trophy this season. Some Spurs fans didn't appreciate his remarks. https://twitter.com/SRTottenham/status/910547018405134336 https://twitter.com/tummore/status/910429999110508544 https://twitter.com/HayroKara/status/910494138205863936 https://twitter.com/DannyT78/status/910253640161644544 You can watch Sherwood, Wright and Kelly Cates discuss Kane and Spurs here: https://www.youtube.com/watch?v=t8E35u2zK4A"According to the most recent figures, which cover the year to June 2016, Spurs' wage bill was around £100 million on turnover of just over £200 million, for a wages-to-turnover ratio of less than 50 per cent. The historic average for the division is just over 60 per cent, so Levy’s cost-control regime already looks aggressive."
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