In the summer of 2012, European champions Chelsea were in the middle of a busy transfer window, signing Eden Hazard, Oscar and Victor Moses.
While promising youngsters Kevin De Bruyne and Romelu Lukaku had returned to Stamford Bridge after successful loan spells and were hoping to get their chance in the first team.
Meanwhile, as the window drew to a close, the Blues went after 22-year-old Spaniard Cesar Azpilicueta in a move that was seen as nothing more than an add-on to the statement business they had already conducted.
In retrospect, the hype surrounding Hazard was more than justified and in today’s ridiculous financial climate, his £32m fee is cheap. Yet Azpilicueta’s purchase for just £7m is even more remarkable.
Last week, the Spanish defender left the club after 11 years, 508 games and seven major trophies that made him a legend and one of the best value buys of the Premier League era.
Cesar Azpilicueta’s crowning moment at Chelsea came in their Champions League win in 2021
The 33-year-old agreed to join La Liga side Atletico Madrid and left Stamford Bridge on a free.
But how does one even go about accurately assessing the value of a transfer? Here at Mail Sport, we have set ourselves the inevitable task of ranking the deals that look extraordinary afterwards.
Team and individual success certainly come into the equation, as does the club’s tenure. Players aren’t ranked specifically based on their ability or career achievements, instead we’ve looked at those who have worked wonders for clubs who got them on the cheap.
We keep free transfers to a minimum – because they probably deserve their own list – and favor frugal purchases.
So with all that out of the way, with Azpilicueta ranking as our No.10, here’s the rest of our list.
9. Edwin van der Sar – £1.5m from Fulham in 2005
Edwin van der Sar was Man United’s first signing after the club bought the Glazers in 2005.
The Dutch stopper was brought in as a short-term solution to United’s persistent problems in goal. The 34-year-old penned a two-year deal, originally planned to pave the way for promising youngster Tim Howard following the departure of Roy Carroll.
Van der Sar ended up staying for six seasons, winning four league titles, two league cups and the Champions League by forming one of the most formidable defensive units behind Rio Ferdinand and Nemanja Vidic.
United’s run of 14 consecutive clean sheets, achieved in the 2008–09 season, is a record that still stands today.
The Dutchman worryingly suffered a brain haemorrhage while on holiday in Croatia last week.
But in an update on his condition on behalf of his wife, Annemarie, Ajax revealed on Tuesday night that while he is ‘still in intensive care’, he is ‘not in danger’.
Edwin van der Sar joined Man United when he was 34 years old and spent six years at the club
8. James Milner – Free signing in 2015
We said we’d keep free signings to a minimum, but some are just too good to ignore. James Milner arrived at a very different Liverpool in 2015.
Coming off a bruising sixth place finish, the club recruited Christian Benteke, Roberto Firmino, Nathaniel Clyne, Danny Ings, Joe Gomez and Milner.
It’s fair to say some of the deals worked out better than others, but at least two of those names played crucial roles in the success the club would enjoy under Jurgen Klopp, who was appointed later that year.
Under the German’s tutelage, Milner became Liverpool’s ‘Mr. Dependable’, playing every minute in whatever position was required and dispatching penalties before the arrival of Mohammed Salah.
The 37-year-old joined Brighton in the summer after collecting a League Cup, FA Cup, Premier League and Champions League with the Reds.
James Milner is currently third in the Premier League’s all-time appearances with 619
7. Andrew Robertson – £8m from Hull City in 2017
Here is a list of defenders who cost more than Andy Robertson in the summer of 2017; Davide Zappacosta, Serge Aurier, Juan Foyth, Benjamin Mendy and Kyle Walker.
Only one of those players can boast more success six years ago and he set Man City back £50m.
Robertson, meanwhile, has gone from strength to strength after arriving from relegated Hull City, forming one half of one of the most devastating back partnerships with Trent Alexander-Arnold.
The Scotland captain’s list of honors at Anfield is the same as Milner’s above, but at 29 he has plenty of time to add to his tally.
Andrew Robertson has picked up 63 assists for the Reds in 267 games since joining.
6. Patrick Vieira – £3.5m from AC Milan in 1996
Patrick Vieira was ready to join Ajax when a phone call from Arsene Wenger prompted him to swap Amsterdam for London in the summer of 1996.
“He was in Holland, he was there to sign, but I knew his agents,” Wenger explained Arsenal.com. ‘I spoke to Patrick and said: ‘Please stop. Come to Arsenal.’
Vieira quickly established himself as a central cog in the French manager’s all-conquering side and was famous as captain as they achieved the remarkable feat of going unbeaten throughout the 2003-04 season.
In nine years at the club, Vieira played 406 times and scored 33 goals, inheriting the captain’s armband from Tony Adams in 2002.
He won three Premier League titles and the FA Cup four times, leaving a void that has never been fully filled after leaving for Juventus in 2005.
Vieira (centre) captained a star-studded Arsenal side that went unbeaten in the 2003-04 season
5. Vincent Kompany – £6 million from Hamburg in 2008
Man City’s 2008 summer transfer window is best remembered for the show stopping signing of Robinho from Real Madrid that signaled the club’s new owner’s intent.
In retrospect, it ushered in a period of dominance for the Manchester side. But the key to their improvement was not found in the elusive Brazilian who infamously believed he was signing for Chelsea, but with a largely underrated Belgian defender.
in 2010-11 Kompany helped guide the Citizens into the top four, racking up half a century of appearances along the way as Roberto Mancini’s side finally emerged as contenders.
A year later, he captained the team as they finally achieved their goal of winning the Premier League. And while Sergio Aguero’s final-day strike has rightly been immortalized, Kompany’s winner against Man United two games before was just as important.
Vincent Kompany played 360 games for Manchester City during his 11-year Etihad career
4. Jamie Vardy – £1m from Fleetwood Town in 2012
If this list was all about expectations versus reality, Vardy would likely have claimed the top spot for a move that was hardly reported and hardly noticed by anyone not connected to Leicester City.
The Foxes plunked down £1m to sign the then 25-year-old, who had terrorized National League defenders and scored 34 goals the previous season.
Looking back at what Vardy has achieved at club and international level, it’s clear that he really had no place to play in the fifth row.
Despite Leicester’s fairytale few years coming to an abrupt end last season, nothing could take away the brilliance of the Premier League, FA Cup and Golden Boot won by the Sheffield native while in the East Midlands.
Vardy is the Premier League’s 15th top scorer with 136 goals in the competition.
3. Nemanja Vidic – £7m from Spartak Moscow in 2005
Nemanja Vidic’s arrival at Old Trafford coincided with the emergence of Alex Ferguson’s last great Man United team.
The Serbian anchored a fearsome central defensive partnership with Ferdinand and captained the Red Devils as they reasserted themselves as the dominant force in England.
Globally, they were second only to Pep Guardiola’s Barcelona, who beat them in two Champions League finals.
Yet while at Old Trafford, Vidic claimed five Premier League titles, three FA Cups and the Champions League in 2008. His £7million signing represented incredible value for a modern icon who went on to make 300 appearances for the club .
Nemanja Vidic joined Man United in the winter transfer window of the 2005-06 season
2. Sol Campbell – Free signing in 2001
To say that Campbell’s 2001 move across north London was controversial would be something of an understatement. The commanding defender lead Spurs to League Cup glory in 1999 and was expected to extend his nine-year stay when his deal expired two years later.
However, Campbell chose to join Arsene Wenger’s exciting Gunners project, where he established himself as one of the best centre-backs of his generation.
Campbell was certainly vindicated in his decision, as were Arsenal, getting their hands on a fine defender who would spend five years at the club.
Two league titles and three FA Cups is pretty good for a free transfer.
Campbell opened the scoring for Arsenal in a Champions League loss to Barcelona in 2006
1. Eric Cantona – £1.2m from Leeds in 1992
Eric Cantona’s importance to the modern myth of Man United is akin to a Johan Cruyff, Thierry Henry or Frank Lampard.
A talismanic figure, championed above all by the manager, who sets new expectations of what is possible thanks to their sensational displays on the pitch.
In short, for United to have unearthed such a pivotal character in their recent history from a rival and for an extraordinary price of £1.2m.
Cantona wasn’t even among the five most expensive transfers that summer, but went on to win four league titles and two FA Cups during his half-decade in Manchester.
Cantona’s purchase from rivals and First Division champions Leeds paved the way for success