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Speaking on the Studs Up podcast, Tim Sherwood has told the tale of when he first saw Jack Grealish play, claiming that he told Harry Redknapp to sign him for Tottenham when he was just 16 years old.

The midfielder was seen as a bright talent from a young age, and Sherwood was seemingly one of the first to spot him and his potential.

The former Aston Villa boss claims that he told Harry Redknapp to sign him in a swap deal as a 16-year-old, but the gaffer turned down the idea because he didn’t think he’d be able to help him immediately.

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“He was different. He just had a raw ability that you would not believe. I remember going to see him when he was 16 playing for the U18s at Bodymoor Heath the training ground of Villa. I was working with Harry (Redknapp) at Tottenham, but I remember going there and going ‘I want to see that kid Grealish play.’ He was playing against our U18s and he didn’t disappoint me,” Sherwood said.

“I remember saying to Harry, we had a player who Villa wanted in the first-team, I won’t mention the players name, and he wasn’t playing at Tottenham, and I said, get rid of him and say ‘give us Grealish and we’ll do a part exchange now’, but Harry was absolutely right, he said he wasn’t going to help him then, and by the time Grealish would’ve been ready to produce, Harry wouldn’t have been there, and no manager would have been, unless you’re Wenger with a 10-year stint or whatever.

“So it just doesn’t happen, so you learn and Harry was right, he wasn’t going to offer him anything and you might have to use the boy who I was talking about who was an established player who’d played international football, but I knew Jack was special.”

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This one must hurt to read if you’re a Tottenham fan.

We all know how close Spurs came to signing Grealish back in 2018, but this deal could have been done even a few years before that.

If Spurs had Grealish they would be a much more frightening force, but unfortunately, Redknapp’s short-sightedness led to them missing out on the midfielder.

Nowadays, signing Grealish would reportedly set you back at least £100m, so it’s fair to say that Spurs missed out on a great deal.

This may go down as one of football’s great ‘what if’ scenarios.

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