After the transfer of Raheem Sterling this summer, sports writer George Hopkins looks at the top five overpriced Englishmen.

Images by Axel Steenberg

“I’d never imagined to be at this point at this age I am now, breaking the British transfer fee,” said Raheem Sterling days after securing a £49million move from Liverpool to Manchester city. In the interview he seemed excited and relieved that the intense period of media speculation was over, but this relief may have been premature.

Sterling is but one in a long line of English footballers whose services demanded a remarkably high transfer fee, so there is a great deal of historical precedent that shows how these moves can pan out. Despite the inevitably differing trajectories of these player’s careers, what they all consistently show is that the time to feel a sense of accomplishment is not when the “i”s are dotted and the “t”s crossed. There is a long road of justification ahead for Sterling and Manchester City – one that the British media will be following every step of the way.

This article looks at five such examples of high-priced Englishman who failed to live up to expectations and the high prices paid for them.

In all honesty, Gareth Barry, Stewart Downing or Ashley Young could have made this list for failing to live up to the hype surrounding their transfers, but as Milner demanded the highest fee it is he who makes it.

5. James Milner

If there was a medal awarded annually to a club who manages to sell English players to bigger clubs for an outlandish fee, Aston Villa would have a much larger trophy cabinet.

Milner was signed for a cash plus player deal (Stephen Ireland) in a deal worth approximately £26million. Having played 201 times for City, his time at the club can’t really be viewed as a failure. That said, paying nearly £30 million for a player whose known more for his work ethic than his ability to determine the outcome of a game – something that has made him an easy target of derision online – does seem rather steep.

4. Luke Shaw

Another side who have embraced the culture of selling their top players to clubs with more financial clout – a strategy that is so far paying off for them – is Southampton.

The transfer that filled their pockets more than any other last summer was selling Luke Shaw to Manchester United for £27 million.

It may seem harsh to include such a young, talented player on this list after just one disappointing season, but all the signs so far point to him spending more time on the therapy benches at Old Trafford than the hallowed turf that he must have dreamed so much about when he put pen to paper. Besides, even if he does manage to stay relatively injury free over the rest of his career, £27 million is a lot to pay for someone who plays at the least important position on the field, fullback, even in the modern era when they are required to do so much more than their predecessors.

3. Shaun Wright-Phillips

A short, pacey winger with undoubted potential who moved from a club who had seen better times to one on the up.

Sounds rather familiar, doesn’t it? A bit too familiar for Manchester City’s liking.

In fact, Shaun Wright Phillips’ entire career can be seen as the worst case outcome for Raheem Sterling.

Back in 2005, Chelsea paid £21million for Wright- Phillips’ services. While that might recently have become a “reasonable” fee for a young player with potential who has grown up surrounded by the culture and pace of the English game, ten years ago that was a great deal of money. Somewhat predictably it was a gamble that did not pay off: Wright-Phillips failed to score for Chelsea for nearly 17 months and moved back to City after just 3 years at the club.

Fast forward to January of 2015 and another club was bemoaning having spent too much money on the Englishman: the then manager of QPR, Harry Redknapp, complained in an interview that Phillips was refusing to leave because of the large contract, a reported £60,000 a week, he was on at the time.

2. Francis Jeffers

The English flop that time forgot.

Jeffers was a terrifically talented youth player who remains one of England’s greatest performers at the U21 level, scoring 13 goals in 16 games – a record he shares with one Alan Shearer.

His time at Everton was similarly impressive, tallying 23 goals in 82 games, so Arsène Wenger’s decision to bring him to North London is somewhat understandable. At £8million he was by no means the most expensive acquisition on this list, but when you consider that Vieira, Pires and Ljungberg were all bought for less, it was a big spend for Arsenal at the time.

After just 22 league appearances over two seasons, Jeffers left Arsenal and ultimately never reached the heights that were expected of him – moving around from club to club, never settling. What makes his fall from grace all the more startling is that Everton’s next touted prospect, Wayne Rooney, scored fewer goals for Everton than Jeffers did, and we all know how he turned out.

1. Andy Carroll

As you may have predicted, the number one spot on this list belongs to the long-haired titan from Tyneside.

It is easy to see why Liverpool did decide to bring him to the club, though. At 6ft 4, Carroll was, and still is, a physical brute who is dominant in the air; it was this skill set that originally earned him a place in the Newcastle during their brief fling with the Championship after many of their more experienced strikers fled because of their relegation, and brought him to the attention of fans and media across the country.

An impressive season in the championship helped Newcastle to bounce straight back into the Premier League, and he continued this form into the start of the 2010-2011 season, scoring 11 goals in 20 games.

Sadly for Carroll, anyone who is bought for a fee as high as £35million has to perform immediately and consistently, something that he was never able to do at Liverpool. This can be partly attributed to his struggle to stay fit, but the truth is that even when he did manage to lace up his boots he always seemed out-of-place at Anfield. Whether he was out of his depth or just a square peg in a round hole is a matter up for debate, but what is for certain is that his transfer, and his overall time at the club, was an abject failure.