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Teenage Kicks: Best & Worst Teenage Transfers

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When Louis van Gaal walks into Old Trafford today he’ll be meeting many of his new charges for the first time. Chief among them will be Luke Shaw, the 18-year-old left-back, who earlier this summer became the world’s most expensive teenager.

The new gaffer won’t have to look too far for examples of the successes and failures of teenage players who’ve moved for big money. Despite some controversial sagas at United, Wayne Rooney has justified his £27 million price tag at the same age as Shaw. However, Anderson has returned from an unsuccessful loan spell at Fiorentina hoping for one last chance to redeem himself following a largely disappointing £25 million move, also at the age of 18.

Here’s a look at some other big- money teenage transfer hits and flops:

Mark Kennedy, £1.5 million
Liverpool broke the British transfer record for a teenager when they splashed out £1.5 million for the 18-year-old winger who’d excelled at Millwall under Mick McCarthy. However, he didn’t get many opportunities at Anfield to prove himself, restricted to just five starts in three seasons at a club already boasting the likes of John Barnes, Steve McManaman and Patrick Berger on the wings.

Pool actually made a profit on him when they offloaded him to Wimbledon, the next stop on a nomadic career that ended at Ipswich Town in 2012. He was an important squad player for Ireland under McCarthy, but is possibly best remembered in his home country for his arrest, along with Phil Babb, for drunkenly damaging the side of a policewoman’s car. Sadly, it was the most damage he’d done on the wing for quite a while.

Robbie Keane, £6 million
The LA Galaxy striker has gone on to be transferred for cumulative transfer fees of over £90 million, making him one of the most expensive players of all-time. However, he was relatively unknown as a 19-year-old who made a £6 million move from Wolves to Coventry City in 1999.

His form after just one season at Highfield Road led to a shock £13 million move to Inter Milan, where “Baby Irish” struggled to supplant the likes of Ronaldo, Christian Vieri, Alvaro Recoba and Hakan Sukur from the first-team. A move to Leeds United’s “babies” under David O’Leary beckoned before spells at a series of British clubs while becoming Ireland’s record goalscorer.

Jermaine Pennant, £2 million
Pennant’s £2 million move from Notts County to Arsenal in 1999 sent shockwaves through English football, with the transfer a record transfer fee for a trainee, who was yet to make an appearance at Meadow Lane. However, a series of disciplinary problems did not go down too well with Arsene Wenger and he made just 12 appearances in his six years at the club.

Sadly his potential was never realised and he’ll be best remembered for losing Porsches rather than opponents and an electronic tag following a prison spell, that weighed as heavily on Pennant as his early price tag. He’s had largely unsuccessful spells at a series of clubs, including Liverpool, and at just 31 has been looking for a new club for the past six months.

Steve Simonsen, £3.3 million
Steve who? In 1998, Tranmere’s Simonsen became British football’s most expensive teenager and goalkeeper after his short move to Everton. He made only 30 appearances for The Toffees before David Moyes’ arrival signaled the end of his career at the club.

He’s had successful spells at Stoke City and Sheffield United but failed to live up to his early promise, with many predicting at the time that the keeper with four Under-21 caps was a future England international. Simonsen, 35, is currently a back-up keeper with Glasgow Rangers.

Theo Walcott & Gareth Bale, £9 million & £7 million
Of course, Shaw is not the first left-back product of Southampton’s respected Academy to make a big-money move as a teenager. He’ll be hoping to emulate his predecessor, Gareth Bale, who since his conversion at Spurs to a more attacking role has become the most expensive player in football history. Van Gaal’s recent tactics for Holland suggest he has a similar attacking role in mind for Shaw.

Southampton’s teenage alumni have generally tended to be a success at their new clubs, including Theo Walcott. He made his £9 million move at just 16 years of age and while the early hype, and bizarre inclusion in Sven Goran Eriksson’s 2006 World Cup squad, didn’t help him at first he’s since gone on to be an integral part of the Arsene Wenger’s side – despite a series of injury troubles.