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John Terry Named 'Incredible' Wasted Talent Who Should've Become Chelsea Legend

Home> Football> Football News> Chelsea

Published 15:59 30 Oct 2025 GMT

John Terry Named 'Incredible' Wasted Talent Who Should've Become Chelsea Legend

The former Chelsea captain gave the former starlet the highest of praise.

Luke Davies

Luke Davies

Featured Image Credit: Up Front with Simon Jordan/YT

Topics: John Terry, Chelsea, Premier League, Football

Luke Davies
Luke Davies

Journalist with expertise covering football - both in England and abroad - as well as combat sports.

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@lukedaviesmedia

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John Terry previously revealed how he thought one former Chelsea youngster could’ve become a legend at the Premier League club before his career took a different route than expected.

Terry, 44, is arguably the best player to have graduated from Chelsea’s Cobham Academy, having joined the Blues’ youth set up from West Ham United in 1995.

The 44-year-old former defender later went on to make 717 appearances for the Stamford Bridge club and helped them win five Premier League titles, three League Cups, one UEFA Europa League, and one UEFA Champions League, as well as earning 78 England caps.

Despite not being as successful or well-known as Terry, a number of other players graduated from Chelsea’s academy before going on to enjoy distinguished careers.

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Former centre-back Michael Duberry progressed to the Chelsea first-team around the same time as Terry before later playing for Leeds United, Stoke City, and Reading.

Terry’s close friend Jody Morris also played for Chelsea and Leeds before embarking on a career in management.

John Terry won five Premier League titles with Chelsea (Credit:Getty)
John Terry won five Premier League titles with Chelsea (Credit:Getty)

But it was another former prospect whom Terry once described as the most talented to have not fulfilled his potential at Chelsea.

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Rob Wolleaston was once tipped for greatness but never reached the heights expected of him during his career.

The midfielder, who is now 45, made just two senior appearances for the west London club despite impressing former head coach Ruud Gullit.

When speaking on Instagram live in 2020, Terry said: “He got chosen to train with the first team at a really young age, 17 or 18, did really well, and Gullit told him he was going to play in the first team in a cup game.

“He then phoned up on the day of the game and said he was sick.

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“All of us, if we were sick or felt like we were at the end of the world, we would have still gone and played the game; we wouldn’t have given up that opportunity.

“He actually did it two or three times, and he was just not mentally ready for the game, but ability-wise, incredible.”

After struggling to break into the first team, Wolleaston was subsequently loaned to Bristol Rovers, Nottingham Forest, Portsmouth, and Northampton Town before penning a permanent transfer to Bradford City in 2003.

He managed just 14 appearances for the Yorkshire club before transferring to Oxford United.

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Rob Wolleaston in action for Cambridge United in 2008 (Credit:Getty)
Rob Wolleaston in action for Cambridge United in 2008 (Credit:Getty)

By 2005, the midfielder had dropped into non-league, where he would play his football for the rest of his career – representing Cambridge United, Rushden & Diamonds, Farnborough, Weymouth, and Harrow – before retiring in 2014.

In all, Wolleaston made 337 league appearances, registering 30 goals, but failed to make the most of his talent.

It is not totally clear what the former Chelsea man does now, but according to his Instagram account, he has a passion for painting.

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