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I asked Tottenham to swap Jermaine Jenas for a teenage Jack Grealish, but Harry Redknapp said no, says Tim Sherwood

It’s well documented how Jack Grealish almost joined Tottenham in 2018, but a move to north London could’ve happened before he even became a pro.

That’s according to former Spurs and Aston Villa manager Tim Sherwood, who’s revealed that another ex-Tottenham boss turned down his suggestion to sign the now-Manchester City and England star.

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Grealish is now a household name

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Tottenham nearly swooped in for Grealish, who begun his career at Aston Villa

It wasn’t until 2015 when Sherwood became Grealish’s manager, as he took over at Aston Villa following Paul Lambert’s sacking.

He also went on to be the manager to hand 19-year-old Grealish his full Premier League debut.

But it turns out Sherwood became acquainted with Grealish – now 27 years old – long before the pair’s time together at Villa Park.

Joining Andy Goldstein for NaijaOnPoint Drive, Sherwood revealed the moment the forward first caught his eye and how he even tried to tee-up a swap deal in order to sign him.

“I watched him when he was 16 against Tottenham’s Under-18s,” Sherwood – who served as Harry Redknapp’s assistant at Spurs at the time – explained.

“I remember going back to the first-team game at White Hart Lane and Redknapp said, ‘Well what was the score?’

“I said, ‘I don’t know H, all I was doing was watch this boy Grealish’, it was incredible. I said, ‘[Villa] want to take Jermaine Jenas, we should do a swap for this boy.’”


Sherwood says Redknapp wasn’t keen on his idea

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Sherwood says Redknapp wasn’t keen on his idea

However, Sherwood went on to reveal that his boss wasn’t too keen on the idea of swapping an unproven teenager for Jenas.

He continued: “Harry, quite rightly, said, ‘He’s only 16, by the time he’s in the first-team I’ll be gone’. As a football manager he’s absolutely right, looking after yourself as you would do.

“But for the club it would’ve been a great move. It would’ve been a great move for Jermaine as he ended up going to Villa [on loan] anyway.”

When asked if Villa would’ve let Grealish go at the time and agree to the deal, Sherwood immediately responded: “Yeah. Absolutely.

Jenas had an uneventful spell with Villa, but Grealish didn’t go the other way

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Jenas had an uneventful spell with Villa, but Grealish didn’t go the other way

“There was more need for Jermaine in their team than there was for a young Jack Grealish.

“That’s when you can nick players, when someone’s desperate, if you want a swap now.

“For the here and now they would’ve taken Jermaine Jenas to try and stay in the league as they were trying to survive for many, many years.”

Sure enough, Redknapp was sacked by Spurs a year after Sherwood’s proposal on Grealish, so it’s unlikely he would’ve witnessed him in the first team as manager.

But Spurs’ interest in Grealish didn’t end after Redknapp and Sherwood left the club.

In 2018, the north Londoners wanted to sign Grealish, and he was so convinced the deal was going to be done that he blew kisses to Villa fans as a farewell – only for the move to fall through shortly after.

Fast forward to 2021, and Grealish did move on from his boyhood club in the end, signing for Man City for a then record-breaking British transfer fee of £100million.

What could have been…

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