Every so often a young player bursts onto the scene in an exciting whirlwind of hype, promise and potential that gets fans salivating over the world-beating feats to come from the starlet. Sometimes they even live up to that lofty early billing too. Yet, far more often, it doesn’t pan out like that at all.
For every Lionel Messi, there are fifty Freddy Adus.
In England we have a habit of getting terribly over-excited about emerging young talents. In many cases it’s harmless enough. Stewart Downing never was the saviour of English football after all, but he’s carved out a perfectly decent career for himself and that’s fine.
On other occasions though, the fall from the lofty perch of superstar-to-be to failed prospect is a long and often undignified one.
Breakthrough moment
In athletic terms, Pennant had it all. Fast, powerful and technically gifted. When he joined Arsenal for £2 million as a 15-year-old in 1999 he looked set to be one of the stars of the new Millennium.
Despite becoming the Gunners’ then-youngest-ever player when he made his League Cup bow a few months after his arrival, he wouldn’t start his first league fixture until 2003 – when he scored a hat-trick against Southampton. That would be as good as it got though, and would prove to be the first of only five league starts for Arsenal in seven years at the club.
What went wrong?
The greatest challenge that faced Pennant’s career was being Pennant. His lack of discipline, behavioural issues and aversion to working hard in training forced a string of managers to lose patience with the winger.
In a career that spanned spells (both loan deals and permanent moves) with 15 different clubs before Pennant finally called it a day in 2017 following a four-month stint with Billericay Town, he never made it beyond under-21 level for the Three Lions.
Where are they now?
Pennant is currently appearing on Channel 5’s Celebrity Big Brother and has recently published an autobiography.
Breakthrough moment
Arsenal academy product David Bentley was a Premier League regular for Norwich City during a loan spell in the 2004/05 season. However, it proved insufficient for the ‘new David Beckham’ to force his way into Arsene Wenger’s plans at Highbury. Bentley eventually got his move away from the North London club to get regular first team football at Blackburn Rovers.
The best form of his career came whilst he was with the Lancashire club, and he earned all seven of his senior England caps before moving on to Spurs.
What went wrong?
Bentley’s career was plagued with injuries, confidence issues and a gambling addiction. He lost his place to Aaron Lennon at White Hart Lane and his career never really recovered, and left having scored two goals in 42 appearances. Loan stints with Birmingham City, West Ham United, FC Rostov and Blackburn Rovers failed to reignite Bentley’s form before he was released by Spurs in 2013. Months later he retired from professional football aged 29 claiming to have fallen out of love with the game, as reported by the BBC.
Where are they now?
Since retiring, Bentley has invested his football fortune into various businesses, including bars and restaurants, a cleaning company and an accounting firm.
Breakthrough moment
Francis Jeffers was a goalscoring teenage sensation for his boyhood club Everton, finding the net 18 times in 49 league outings for the Toffees. The youngster’s form was so great that when he made his move away from Goodison Park, the Merseyside club received a whopping £8 million for the striker (big money in 2001 for such a young player).
The club who paid it? Arsenal (there’s a pattern emerging here).
What went wrong?
Injuries struck, Thierry Henry was too brilliant to displace, and it turned out that Jeffers simply wasn’t as good as everyone thought he might be. In this most glorious period of the Gunners’ history, Jeffers barely got a kick. He was loaned back to Everton for the duration of Arsenal’s historic Invincible season but failed to score a single league goal in his second spell with the club.
When he left Arsenal for good in 2004 he had one England cap and 30 career goals to his name in all competitions. 9 seasons and 10 clubs later, with only a further 22 goals under his belt, Jeffers was released by Accrington Stanley and failed to find a new club.
Where are they now?
Jeffers has been part of the under-23s coaching staff at Everton since 2016.






