Most expensive left-backs ever

Sat 13 November 2021 | 20:29

Who are the most expensive left-backs of all time? Were any of these expensive signings an actual success? Follow us below as we take a look at some of the most expensive left-backs in history and delve deeper into their careers throughout the years.

Football has changed quite drastically since it was introduced to the world in 1863. Not only the rules of football, but also and especially the tactics used in the game have evolved into modern strategies we see managers implement into their games. This change in tactics has also caused a lot of transformation for certain roles on the pitch and one the left-back is one of these particular roles.

While left- and right-backs were traditionally deployed as strong defenders alongside the center-backs, we see so many teams deploy their full-backs in a rather offensive form, in which these players make good use of their stamina and run up and down the pitch throughout the whole game. Modern football has basically turned full-backs into one of the most essential parts of almost any team and formation, which is why top teams in Europe are now spending millions to bring in the most talented left-backs and right-backs from all around the globe.

Surely you too are eager to know more about the

most expensive left-backs ever

as the competition for the best left-back in the world is now wide open since many exciting prospects have also set foot onto the big stage. So without further ado, let us take a look at some of the most expensive left-backs in history and provide detailed information about their careers.

Most expensive left-backs of all time

From former Real Madrid player Fabio Coentrao, to Manchester United’s Luke Shaw and Manchester City’s Benjamin Mendy, there are many exciting players on this list of world-class players with world-class transfer fees. Let’s see who else is on this list down below.

Alex Sandro

  • Transfer: FC Porto – Juventus

  • Transfer fee: €26M

Brazil has always produced great players in all positions and we have seen some legendary Brazilian left-backs grace the pitch in recent times. From Roberto Carlos to Marcelo and Alex Sandro, the Brazil national team has always had quite an impressive squad depth on the left side of the pitch. While Carlos is now retired and is enjoying life as one of the greatest left-backs of all time, it is up to Alex Sandro to keep representing the image of a world-class Brazilian left-back.

Sandro is not only one of the best full-backs in the world, but also one of the

most expensive left-backs in history

thanks to his big-money move from

FC Porto

to Juventus back in 2015. Having joined Porto from Maldonado in 2011, the Brazilian managed to rise up the ranks and prove himself to be one of the best around, which was why Juventus were convinced he was worth a massive €26 million in 2015.

As one of the most expensive left-backs ever, the former Porto man realized his true potential at the Italian side, for whom he has made well over 200 appearances over the years, having scored 14 goals and provided 30 assists in the process. The immensely versatile left-back is an all-around defender who can both rush forward to help the attack and also drop back to solidify the team’s defense in a matter of seconds.

Sandro has so far managed to conquer Italy with


as he has managed to win 5 Scudetti, 4 Italian Cups and 2 Italian Super Cups with his current club. The 30-year-old’s record as one of the most expensive left-backs ever might not stand the test of time as clubs are paying eye-watering amounts of money to sign the most exciting prospects of each season.

Kieran Tierney

  • Transfer: Celtic – Arsenal

  • Transfer fee: €27M

Scotland are slowly rising up to the big stage by producing more world-class players every year. One of the most exciting talents that the nation has produced is none other than Kieran Tierney, who is already one of the

most expensive left-backs ever

thanks to his whopping €27-million move from




. Tierney rose up the ranks at Celtic’s youth academy and graduated from the same academy in 2016 when he joined their senior squad and went on to impress even more with his speed and versatility.

The 24-year-old is considered to be one of the most promising left-backs in Scotland, which is exactly why the Gunners opted to sign him in the first place. While his first season at Arsenal was filled with silly mistakes that drastically lowered expectations, Tierney has since managed to bounce back and become one of the club’s main players. He had already made more than 150 appearances for Celtic before joining Arsenal in 2019, having scored 8 goals and provided 37 assists throughout the process.

Now, after more than two years with the Gunners, Tierney has made more than 70 appearances for the Premier League side and has managed to contribute to their games with 3 goals and 9 assists in the process. Perhaps the Scotsman should work a bit more on his defensive game as Arsenal have been struggling here and there.

Leonardo Spinazzola

  • Transfer: Juventus – AS Roma

  • Transfer fee: €30M

There are few players in the world who have spent as much time on loan as Leonardo Spinazzola. The Italian has moved around so much that he has created a long list of football club names. Having graduated from Juventus’ youth academy in 2012, Spinazzola went on to spend his time on loan at clubs such as Empoli, Virtus Lanciano, Siena, Atalanta, Vicenza, Perugia and Atalanta again as he tried his best to prove himself to his parent club.

However, it was still not enough for Juventus and the left-back was simply fed-up from the treatment that he used to get from the former Serie A champions. That is why he decided to join

AS Roma

for almost €30 million in 2019, which in turn made him one of the

most expensive left-backs of all tim

e. The former Juventus man is one of the hardest-working left-backs in Italy and has also gotten himself more than 15 international caps since being called up to the senior national team in 2017.

The 2020 European champion is greatly versatile and can be deployed in almost any position on the pitch. But the main position that he plays in and feels the most comfortable is certainly the left-back. Spinazzola has already made more than 70 appearances for Roma, having scored 4 goals and provided 11 assists in the process as well. As one of the most expensive left-backs ever, the 28-year-old can help Jose Mourinho build a title-winning team in the coming months as they are currently sitting fourth on the league table at the time of writing.

Fabio Coentrao

  • Transfer: Sporting CP – Real Madrid

  • Transfer fee: €30M

Few players on the list of

most expensive left-backs ever

can say that they have won the Champions League, let alone winning it twice. That is why Fabio Coentrao is a rather special case on this list as he has two UCL titles on his CV. The former

Real Madrid

man is by far one of the most successful defenders around as he has made himself quite a full trophy cabinet over the years.

Even though his career did not go the way he wanted as he declined pretty fast compared to his counterparts, the Portugal international is still remembered by many as one of the best left-backs in Portugal history. Coentrao spent many years out on loan at different clubs such as Nacional, Real Zaragoza and Rio Ave before finally making his dream move come true as the Spanish giants paid €30 million to acquire his services in 2011.

The 33-year-old has won two Champions League titles, two La Liga titles, the Spanish Cup, the Supercopa de Espana, the Portuguese league, three Portuguese League Cups, two UEFA Super Cups and 3 FIFA Club World Cups throughout his career. A long time has passed since those glorious days and the Portuguese left-back is now a free agent after having spent several seasons on loan at clubs such as Monaco and Sporting CP. He did take a career break in 2019 but came out of his break in 2020 as he joined Rio Ave on a free transfer deal once again.

Sergio Reguilon

  • Transfer: Real Madrid – Tottenham

  • Transfer fee: €30M

It seems a bit odd that even though Real Madrid are lacking the usual squad depth that they are used to, they just simply let go of their most exciting talents. From Achraf Hakimi who went on to become one of the most expensive right-backs in the world at



Paris Saint-Germain

, and Theo Hernandez, who has proven himself to be one of the best left-backs in the world at AC Milan, there have been numerous young talents who were simply mistreated by Los Blancos.

One such exciting prospect is Sergio Reguilon, who gained prominence as a great left-back during the rather short managerial spell of Santiago Solari. However, with the Argentine’s departure from the club, Reguilon was once again pushed aside by the club after Zinedine Zidane’s return. That is why Florentino Perez opted to sell the young left-back for about €30 million in the 2020 summer transfer window. Reguilon joined Tottenham with a lot of promise and became one of the most expensive left-backs ever thanks to his whopping transfer fee.

The Spaniard is quite happy with his choices as he currently plays for the Premier League side, for whom he has made over 45 appearances and has even managed to provide 8 assists in the process. Those who join Real Madrid usually leave the club with a bag full of trophies, but the Madrid-born left-back was unlucky enough to play for Los Blancos during their worst time as they only went on to win the FIFA Club World Cup.

Abdou Diallo

  • Transfer: Dortmund – PSG

  • Transfer fee: €32M

If it weren’t for Abdou Diallo, we might not have mentioned Alex Sandro at all. The France-born Senegalese left-back is the reason behind Sandro being mentioned on the list of most expensive left-backs ever as he has set two distinct records throughout his career so far. Diallo actually made it into the list on two occasions, once with his move from Mainz 05 to

Borussia Dortmund

and once with his move from the German club to Paris Saint-Germain.

Having risen up the ranks at FSV Mainz 05 in the single season that he spent at the club, Diallo quickly joined Borussia Dortmund for a fee of €28 million and became one of the most expensive left-backs ever. It certainly did not take him very long to impress everyone with his incredible performances as he once again managed to earn a big-money move to yet another world-class club in Europe only a season after joining Dortmund.

Paris Saint-Germain opted to offer €32 million to acquire Diallo’s services in 2019 and that is how the Senegal international got on this prestigious list for a second time in only two years. The versatile defender has been developing his game with a lightning-fast pace and is on his way to become one of the best left-backs in the world. The 25-year-old has already made more than 65 appearances for the Parisians and has managed to impress both the critics and the fans with his solid performances week-in week-out.

Diallo already has a full trophy cabinet with two Ligue 1 titles, two French Cups, two French Super Cups and the French League Cup, most of which he has won since joining PSG. The 2016-17 Ligue 1 title is the only trophy that he hasn’t won with PSG as that particular title dates back to the time Diallo spent at Monaco before joining Mainz in 2017.

Luke Shaw

  • Transfer: Southampton – Manchester United

  • Transfer fee: €37.5M

England have quite a squad depth when it comes to full-backs. From Trent Alexander-Arnold and Aaron Wan-Bissaka rocking it on the right to the likes of Ryan Sessegnon and Luke Shaw holding the left flank, there are numerous English talents who have made a name for themselves throughout their short but at times illustrious careers so far. Luke Shaw is not only one of England’s future hopes, but also one of the most expensive left-backs ever. The Englishman gained quite the attention during his spell at


, with whom he spent two years after graduating from the club’s youth academy.

Even though Shaw’s actual market value was around €13 million,

Manchester United

opted to pay a whopping €37.5 million to sign him from Southampton in 2014. He had made a total of 67 appearances for the Saints before joining United. The now 26-year-old left-back has since managed to become one of Manchester United’s most vital players and is only a few games away from making his 200th appearances for the Red Devils.

Throughout these appearances, Shaw has managed to score 3 goals and provide 18 assists, while also helping his side keep a clean sheet in dozens of games. The Englishman is versatile enough to be deployed as either a left-winger or a center-back as well, which gives his current managed Ole Gunnar Solskjaer the freedom of mind when it comes to picking his starting-XI.

Despite United’s poor run of form since Sir Alex Ferguson’s departure in 2013, the former Southampton defender has managed to win the English League Cup, the Europa League and the Community Shield with Manchester United since joining the club in 2014. Shaw is also one of the highest paid left-backs of all time with a stunning weekly-wage of €190,000.

Ferland Mendy

  • Transfer: Lyon – Real Madrid

  • Transfer fee: €48M

It seems a bit strange that Real Madrid let go of their own talents so easily and for such low prices and then opt to sign other young talents for a lot more money afterwards. But that is how Los Blancos have operated throughout the years and have been quite successful as well. Perhaps the reason the club decided to sign Ferland Mendy was that the Frenchman is well-suited for defensive tactics and rarely sprints forward to help the attack.

But ever since Carlo Ancelotti’s return to Real Madrid, Mendy has been pushed aside for a more conventional Real-like defensive four. Mendy rose up the ranks as one of the most promising left-backs at Olympique Lyon, whom he joined from AC Le Havre for a mere €5 million in 2017. It didn’t take him long to convince Los Blancos to splash the cash and spend a massive €48 million to sign him in 2019.

The former Lyon defender has made over 70 appearances for the Spanish giants and has scored some vital goals throughout the years as well, which have certainly helped Madrid win the double in the 2019-20 season by snatching up the La Liga title and the Supercopa de Espana. The France international is one of the

highest paid left-backs of all time

as well thanks to his whopping €180,000 weekly wage.

The question that remains is that will Ferland Mendy manage to take Marcelo’s throne at Real Madrid and become the club’s main left-back for years to come? Or will he go on to be yet another mediocre signing made by the Royals of Madrid in recent years?

Ben Chilwell

  • Transfer: Leicester City – Chelsea

  • Transfer fee: €50M

Ben Chilwell is yet another one of those English talents who have already managed to make a name for themselves in the world of football despite their young age. Chilwell is currently 24 years old and is already considered to be one of the most effective left-backs in the Premier League.

Of course he might have hit a slump recently with fewer chances to prove himself to his new manager, but there is no denying the fact that Chilwell comes with a lot of potential. The Englishman is a diamond in the rough and has the potential to become one of the best left-backs in the world if he puts enough effort into his game.

While he managed to make a total of 27 league appearances for Chelsea last season, Chilwell has not been as active this time around as Thomas Tuchel prefers to play with three main defenders at the back instead of the conventional four. This has in turn made things difficult for the Englishman as he has to compete for a spot amongst the midfielders instead of proving himself as a proper left-back.

Having joined



Leicester City

for a whopping €50 million in 2020, Chilwell is close to making a total of 50 appearances for the Blues of London and has already contributed to the team’s offense with 6 goals and 7 assists. He has also won three of the most important major trophies in the world, which are the Premier League, the Champions League and the UEFA Super Cup.

Benjamin Mendy

  • Transfer: Monaco – Manchester City

  • Transfer fee: €57.5M

Benjamin Mendy might be one of the highest paid left-backs of all time and might have cost Manchester City a mind-blowing €57.5 million, but the Frenchman has not lived up to the billing in any shape or form. Mendy is not only a true flop football-wise thanks to his constant injuries, but also a flop in life after he was convicted of rape charges, which resulted in him being sentenced to spend a year in jail and add his talent to the very famous “Prison FC”.

The 27-year-old’s market value currently stands at €10 million only thanks to his status as a Manchester City player. Other than that, he has nothing else to show for except the fact that he is somehow a World Cup winner.

The France international was simply amongst one of those called up for the national team as he only played 40 minutes for Les Bleus and got his name amongst the 2018 World Cup winners in Russia. We will have to wait and see if the former Monaco left-back can ever bounce back and once again rise up the ranks to prove his worth.




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