1. Willie Groves (West Bromwich Albion to Aston Villa, 1893, £100)



In an ideal world, the entire blame for football's modern descent into multi-million money madness would be laid at the door of cartoon villains such as Rupert Murdoch, Roman Abramovich, Sheikh Mansour, Florentino Pérez, Kia Joorabchian, Damien Comolli and Jim White, capitalism's unthinking cheerleader from off the telly. If you're a Tory, or devoid in some other way of basic human decency, you may care to finger Jean-Marc Bosman, George Eastham or Jimmy Hill, the brave workers who stood up to be counted and whose battles ensured footballers would no longer be ragged-short-trousered philanthropists. But in truth, money has talked loudly in football pretty much from the get-go.

"Football is a big business," wrote the league founder William McGregor in a 1905 partwork called The Book of Football. "The turnover of some of our clubs is considerably larger than the turnover of many an important trading concern." This only two decades after Preston North End finally let the genie out of the bottle. Preston were disqualified from the 1883-84 FA Cup for fielding professionals, the FA still backing the thoroughly disingenuous posing of the public school and university types who insisted the game should only be played for fun, which was easy to say if you could afford to take the time off work to play. The northern and Scottish clubs and players weren't having it, and Preston's fate instigated a debate which led to the legalisation of professionalism.

It wasn't long before the English game was awash with cash. One of the first to notice was Darlin' Willie Groves, a stocky and powerful striker with Hibernian, who knew his own value. Having earned good money as a stonemason, he wasn't about to be left out of pocket. He was accused of trousering illegal wages when helping Hibs to the 1887 Scottish Cup. (Yes kids, Hibs did once win Scottish Cups, ask your great-great-great-great grandad.) He left to join the newly formed Celtic Football Club in 1888, then headed south to the world of professionalism, and West Bromwich Albion, via a contract dispute with Everton.

Groves was one of the stars of West Brom's 3-0 FA Cup final win against Aston Villa in 1892, a match that led to great bitterness and recrimination. Not only was the Villa keeper Jimmy Warner accused (unfairly and inaccurately) of throwing the match, having supposedly placed a wager on the opponents, West Brom's goalscoring hero John Reynolds was accused by his own board (!) of only bothering in the big games in the hope of landing a transfer. When Villa came in for Reynolds and his team-mate Groves, they were accused of tapping up and were forced to pay £25 in fines – they paid £50 for Reynolds, and a barrier-breaking £100 for Groves.

Groves won the league with Villa before kicking off about money again, and returning to Scotland. Much good his cash-conscious ways did him, for the money only lasted so long and, after a period of illness, he died penniless at the age of 38. Reynolds too died in abject poverty, aged 48. Warner left the country in the wake of the match-fixing allegations. But football marched on. And while the numbers have long changed, much still stays the same. In the aforementioned Book of Football article, McGregor notes that Middlesbrough made a net loss in 1904-05 of £1,035 2s 5d. They'd just broken the world transfer record for Alf Common, the first £1,000 player, in doing so living very much beyond their means. Boro: the Real Madrid, Manchester City and Paris St-Germain of their day. History, it seems, teaches us nothing. SM

At his press briefing the day before Arsenal arrived to wrap up the 2001-02 title race at Old Trafford, Sir Alex Ferguson embarked on a famously volcanic rant at journalists. Even by the standards of the spiky and paranoid Scotsman, it was quite the bollocking. "He is a fucking great player," he said in closing, after ordering the press-pack off the premises. "And you are all fucking idiots." The "he" in question was Juan Sebastián Verón, then a British record signing at £28.1m from Lazio. An out and out playmaker, he arrived in England in 2001 under a legal cloud with the validity of his passport being questioned in Italy. Such was the barrage of media criticism to which he was later subjected, he left Manchester United two seasons later under a professional one with his validity as a footballer under the same intense scrutiny.

An undeniably "fucking great player" who had proved his worth before his move to United and would do so again after an unhappy time in England, his two-season spell at United was, by his own high standards, a failure, although nowhere near as disastrous as some would have you believe. Regularly portrayed in the press for being the personification of money squandered, the opprobrium heaped upon the Argentinian by British football writers was a source of extreme irritation for Ferguson, who understandably saw it as an attack on his own judgment. At the end of a season in which Arsenal won their second Premier League and FA Cup double in four years and United finished without a trophy for only the third time in 13 years, it was small wonder he spectacularly blew his top.

Contrary to reports that Verón's boyhood dream had been to play for Sheffield United, like his uncle Pedro Vere, the man they call La Brujita (Little Witch) would later insist he grew up hoping to one day for sign for Manchester United, against whom his father, Juan Ramón (aka La Bruja, The Witch) had played twice for Estudiantes in the 1968 Intercontinental Cup. At Verón's Old Trafford unveiling he was shown around the club's museum, where an Estudiantes pennant with his father's caricature apparently still resides. "Imagine my feelings!" he said in a subsequent interview with FourFourTwo magazine. "At the moment, I was trying not to think much about it, but when I was alone, it was really emotional."

It was about as good as things got for Verón at Old Trafford, albeit not through any great fault of his own. Originally purchased after United had failed to break down Bayern Munich in the previous season's Champions League quarter-finals, it seemed Ferguson may have bought the classy Argentinian without having any clear idea quite how he was going to accommodate him in a midfield comprising such talents as David Beckham, Paul Scholes, Roy Keane and Ryan Giggs. The player's confidence suffered during the subsequent season of experimentation, in which he was dogged by a nagging achilles injury, and after United's exit from the following season's Champions League at the hands of Bayern Leverkusen, Ferguson was forced to deny that Verón had been openly criticised by two team-mates who were angered by his peripheral performances over both legs of a semi-final United lost on away goals.

A sublime player who made and scored goals and could pass the ball through the eye of a needle, it would be harsh to judge Verón's second and final season at Manchester United as an abject failure. In the Champions League he excelled upon being given free rein as the midfield fulcrum from where he conducted the United orchestra when available. Having bought him despite not particularly needing him, considering he already had Scholes, Ferguson decided he no longer wanted his piratical acquisition and sold him on to Chelsea for a little over half of what United had paid. Once again, Verón was underwhelming and it was not until his 2007 return to Estudiantes, where he was installed as a playmaker, that he was able to once again demonstrate the qualities that had made him enough of a success at Lazio to earn his record move to United. BG

3. Denílson (São Paolo to Real Betis, 1998, £21.5m)



There was no doubt about Brazil's star attraction at the 1998 World Cup. Ronaldo was the player every kid in the playground wanted to be, the player everyone wanted to see on the ball all the time. He was already a household name in Europe, too, after that stunning, solitary year at Barcelona was followed up by an impressive debut season at Internazionale in the lead-up to the World Cup. There was no mystery. People knew what to expect, even if that did not mean they knew how to stop him. We all watched Football Italia.

Yet when it came to judging those who played outside Europe, it was more difficult 15 years ago. Now everything is at our fingertips. It only takes a flick of a switch. If you wanted to be clued up about Paulinho before he signed for Tottenham, it did not require Herculean efforts to watch him play for Corinthians. But back then, there was no Twitter or YouTube. You couldn't stream matches on your computer or watch South American football on television; instead people relied more on word of mouth and had to wait to see for themselves, usually at a World Cup, and that is why there was so much intrigue surrounding another rising Brazilian talent: Denílson.

To listen to the type, here was a player who would go on to be a multiple Ballon d'Or and Champions League winner. Having made his debut at the age of 17 for São Paulo in 1994, the left-winger made his international debut in 1996 and impressed as Brazil won the Confederations Cup a year later. Yet it was at the World Cup where he would be introduced to the wider public.

By then, excitement was building. Denílson had rejected a host of top clubs, agreeing to move to Real Betis in a world-record £21.5m deal, and everyone wanted to see what all the fuss was about. It was not immediately clear, though, mainly because the 20-year-old was restricted to cameo appearances off the bench. It was the stepovers, the blur of feet, that caught the eye, yet there was rarely any suggestion that he would dominate and when he was introduced at half-time in the final with Brazil trailing 2-0 to France, he could not find a way past Lilian Thuram.

So off he went to Betis, who had qualified for the Uefa Cup after finishing eighth in La Liga. Yet Denílson, weighed down by the expectation that came with his transfer fee, struggled and Betis made an early exit from Europe and were disappointing in the league, finishing 11th.

Denílson was seen as an expensive flop and he returned to Brazil in 2000, joining Flamengo on loan after Betis were relegated. Perhaps he had simply failed to live up to the hype though. He wasn't a terrible player and he did return to Betis in January 2001, helping them win promotion. He spent another four years in Spain, playing almost 200 times for Betis, before leaving for good in 2005. Then, after an unsuccessful season with Bordeaux, his career took a turn for the nomadic, as he moved from the US to Brazil to Vietnam to Greece, where he retired in 2010.

Despite everything, he was included in Luiz Felipe Scolari's Brazil squad for the 2002 World Cup and even made a late appearance in the 2-0 victory over Germany in the final. It is easy to mock, but he has one more World Cup winners' medal than any of us will ever own. JS

4. Ruud Gullit (PSV Eindhoven to Milan, 1987, £6m)



It was a record transfer in every sense of the word. With suitors across Europe chasing the signature of Ruud Gullit, the distinctively dreadlocked two-times Dutch player of the year who had propelled PSV Eindhoven to consecutive Eredivisie titles, the 24-year-old and his representatives travelled to Italy in 1985 to hear what the Milan owner, Silvio Berlusconi, had to say. Pleasantries were exchanged, terms were talked and perhaps feeling a prospective deal was slipping away from him, the future Italian prime minister played his ace in the hole.

Spotting a piano in the lobby of the hotel in which they had convened, the one-time cruise-ship crooner pulled up a stool, flexed his fingers and began to serenade Gullit by playing La Vie En Rose, the signature song of the French diva Edith Piaf.

Bemused, flattered, mesmerised and probably slightly scared by the haunting sound of an elderly Italian sexaholic business tycoon cooing that "It's he for me and I for him, throughout life, He has told me, he has sworn to me for life", Gullit was sold … metaphorically and literally. It was a smart move; his subsequent £6m world record transfer to Milan was an unequivocal success. The perfect pitch had clearly been pitch perfect and clinched the deal, although given what we've learned about Berlusconi and his Bunga Bunga parties in the interim years, the less said about "the endless nights of love" referenced in Piaf's song, the better. BG

5. John Charles (Leeds United to Juventus, 1957, £65,000)



On 24 March 1951 after an injury sustained by the team's centre-forward Len Browning during the previous day's Good Friday defeat by Hull City, Major Frank Buckley, the Leeds United manager, gambled on selecting his 19-year-old Wales centre-half John Charles at centre-forward for the Easter Saturday Division Two match against Manchester City at Maine Road. It didn't work, Charles rarely touched the ball and Leeds lost 4-1 but on Easter Monday he kept the No9 shirt, scored twice against Hull at Elland Road, scored once more in a further two run-outs up front that season but returned to the heart of defence the following campaign, which was curtailed by injury and National Service commitments. After 12 games at the beginning of the 1952-53 season at the back, Buckley again gave Charles the centre-forward role and this time, within a few matches, he was terrorising defences. He combined powerful running, a calm authority, unselfishness, balance, two excellent feet and a devastating indomitability in the air that enabled him to flourish in either role. In 28 matches that season after the switch he scored 26 goals, 42 goals in 39 games the next and four in six in 1954-55 before Buckley's successor, Raich Carter, was forced to shore up his defence with his best player.

In 1955-56 Leeds were promoted with Charles playing eight games at centre-half, four at right-half, 14 at inside-right and 15 at centre-forward: 41 matches in which he scored 29 times. In Division One, with Jack Charlton now a regular in Charles's old position, he played exclusively in the forward line and scored 38 times in 40 appearances. By then Charles had been acclaimed by Nat Lofthouse as the best defender he had ever faced and by Billy Wright as the finest striker he had ever seen. Little wonder, then, that Leeds had been fending off bids for their key player for five years, though back then with a maximum wage and no freedom of contract, unless the club urgently needed funds boards were under no constraints to sell.

On the night of Tuesday 18 September 1956, however, with Leeds second in Division One, Elland Road's West Stand burned down. The club's offices and dressing rooms had been housed in that stand and the losses were considerable – all the kit, the players' boots, balls and United's entire archive of paperwork, records and memorabilia were destroyed. Remarkably Saturday's home match against Aston Villa went ahead with the players changing into hastily sewn replacement strips in nearby houses after the chairman had asked residents along Elland Road to provide emergency accommodation. Charles scored in a 1-0 victory but the cost of the replacement stand, estimated to be £100,000, was never likely to be raised by the insurance settlement on the old one or from the relatively modest personal funds available to the directors.

After the fire Leeds received firm inquiries from Internazionale, Juventus, Lazio and Real Madrid. Gigi Peronace, a man for whom a job description would be inaccurate and restrictive – a polymath fixer, agent, scout, general manager, executive, interpreter, sounding board and liaison officer – had first been to watch Charles in training at Elland Road in 1955 and made contact with the player in April 1957 after a Leeds defeat at Highbury. Umberto Agnelli, the president of Juventus, then travelled to watch Wales play Northern Ireland at Windsor Park and a week later cabled the Leeds chairman, Sam Bolton, telling him to expect his arrival in the city to discuss the transfer.

Charles's agent, Teddy Sommerfield, took the train to Leeds on 18 April with Kenneth Wolstenholme to advise him and booked into the Queen's Hotel where Charles, dodging photographers and entering through the kitchens, met them in room 222. The hotel's Italian waiters, Charles reported, proceeded to do the best promotional work for Juventus possible, even before Agnelli and Peronace arrived, extolling the beauty of the country and the potential of the team.

The first meeting between the two clubs took place in a factory on the outskirts of the city before reconvening in room 233 at the Queen's. After an hour agreement was reached over a £65,000 deal, £55,000 for Leeds and a £10,000 signing on fee for Charles. The talks between the player's representative and Agnelli were more protracted before Sommerfield settled for £70 a week for his client, a £25 away and £15 home win bonus, a car and apartment of his choice.

Britain's costliest player and still, in this author's opinion, its best, led Juventus to the title in his first season with the Bianconeri, scoring 29 times and being named footballer of the year, formed a prolific partnership and friendship with the Argentina and Italy inside forward Omar Sívori, opened a restaurant, recorded two albums' worth of songs and won two further scudettos, two Italian cups and in 1997 was voted Juve's greatest ever foreign player. He returned to Leeds for an ill-fated 11-game spell in 1962 for a fee of £53,000 which was quickly recouped by selling him on to Roma.

His considerable physical attributes and particularly his strength – "he seemed to hover over opponents looking like an eagle among sparrows, a predator surveying lunch," wrote Michael Parkinson – were twinned with a self-effacing and placid character. He never retaliated, was never cautioned or sent off. If he used his wealth unwisely over the years until it was frittered away and in the 1980s and 1990s he could be found once a fortnight in the unpretentious Elland Road West Stand bar that bore his name and his transfer had helped to build 40 years previously, no one had deserved it more than Charles, Juve's imperishable "Il Gigante Buono". RB

6. Tore Andre Flo (Chelsea to Rangers, 2000, £12m)



The record purchase by a Scottish club was, contrary to received wisdom, no flop. The Norwegian striker's 29 SPL goals in 53 appearances following his £12m transfer from Stamford Bridge in November 2000 is more than satisfactory and he ended both his seasons at Ibrox as Rangers' top scorer.

What he symbolised, though, was Rangers' swagger under David Murray when challenged by a Celtic who had been hitherto parsimonious by comparison in the transfer market. When Martin O'Neill was appointed as manager of Celtic in the summer of 2000 he spent almost £20m over six months on six players including Chris Sutton for £6m, Joos Valgaeren for £3.8m and Neil Lennon for £5.75m.

When Sutton was bought from Chelsea in July he became Scotland's record transfer purchase. In 1998 when Celtic had ended Rangers run of successive league titles at nine, Murray's bombast had been evident in his pronouncement: "For every five pounds Celtic spend, we will spend 10." He was as good as his word in November 2000, offering Chelsea's chairman, Ken Bates, double the fee he had received for Sutton for Flo.

The Norwegian had started the season at Stamford Bridge as part of a three-man attack alongside Gianfranco Zola and Jimmy Floyd Hasselbaink but had resumed his role as a substitute under Claudio Ranieri after Gianluca Vialli had been sacked five games into the campaign. "The new coach told me I was part of his plans and that I would play more games," he said in October. "But I have to be on the pitch to score and it's not helping me internationally. I have played almost 50 games for my country and don't want to be sitting on the bench." A week later the Guardian reported that Aston Villa's bid of £10m had been turned down and they had been told to return with £15m while the deposed Vialli said his valuation was closer to £17m, £2m more than he had paid for Hasselbaink. On 23 November Chelsea accepted Rangers' offer of £12m but only "reluctantly".

"Flo's been put under a lot of pressure by Norway's manager who has told him that if he doesn't play more regularly he could lose his international place," said Chelsea's managing director, Colin Hutchinson. "Tore is very patriotic and that means a lot to him. He has undoubtedly become frustrated at the lack of starting chances at Stamford Bridge. I think a little bit of work behind the scenes from people advising him has made this move come about."

Flo made his debut for Rangers in the Old Firm game three days after his move, scoring the second goal in a 5-1 victory but Celtic went on to win the league by 15 points and the following season's title by 18 points by which point Alex McLeish had replaced Dick Advocaat as Rangers manager and was looking for a more direct option up front, selling Flo to Sunderland for £6.75m where anyone who had ever seen him play could have told Peter Reid that he was not going to suit his system in a role designed for Niall Quinn. Rangers won the title the season he moved south while Sunderland were relegated but what he achieved on the pitch at Ibrox was secondary to what he symbolised to Murray, not so much keeping up with the Jones's by buying a bigger car but sticking a bloody great yacht on his drive to demonstrate his status as someone, in the old Harry Enfield fashion, "considerably richer than you". RB