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When we’re talking about moments that changed the history of football, they don’t get much bigger than the Bosman Ruling of 1995. For those who’ve forgotten or don’t know, the ruling was a legal decision that meant that once players reached the end of a contract with their club, they were free to join another club with no transfer fee involved.
The debate over whether this is a good thing for football rages on – it’s certainly allowed players to maximise their worth in the market, but it’s also led to way too much power for agents representing said players – but it’s certainly meant that a lot of top level players have been able to move, and have massive success as free agents.
Here, then, is a full XI of the best free agent signings of the 21st century.
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Goalkeeper: Iker Casillas
Spanish goalkeeper Iker Casillas became a legend of the game during his time at boyhood club Real Madrid, where he won 3 Champions Leagues and 5 La Liga titles across 725 appearances in 16 seasons. In 2008 he was even awarded a ‘contract for life’ with the club – in reality, a contract extension to keep him at the Bernabeu until 2017.
Unfortunately though, that didn’t pan out and after a fall-out with club president Florentino Perez, Casillas was let go by Los Blancos at the end of 2014/15, leaving largely under a dark cloud. At the age of 34 he could’ve been forgiven for simply fading out of the game, but instead he signed with Portuguese club Porto as a free agent in time for the start of 2015/16.
From there, the legendary keeper proved that he still had the magic that made him one of the world’s best; 2015/16 saw him break the record for the most clean sheets in Champions League history, while 2016/17 saw him set a new personal record for clean sheets during a single season with 16.
2017/18 went even better, as Casillas helped Porto to win their first Primeira Liga title since 2013, and he’s since become the only player to appear in 20 Champions League editions as well as just the second player to win 100 Champions League games. Not bad for a goalkeeper simply let go by Real Madrid for nothing!
Defender: Dani Alves
Brazilian full-back Dani Alves largely made his name at Barcelona, where he was part of Pep Guardiola’s all-conquering side of the late 2000s and early 2010s. He won 6 La Liga titles and 3 Champions Leagues with the Catalan side, but despite becoming one of the most expensive defenders ever when he signed for them for around £30m in 2008, he ended up leaving the Nou Camp for free in 2017.
Despite being 33 when he was released by Barca, Alves has remained at the top of the game ever since – and has made another successful move as a free agent, making him a definite for a list like this.
His first move took him to Italian giants Juventus, where he was a huge hit, playing a key role in The Old Lady making the Champions League final in 2016/17 and winning the Serie A title with the club.
After just one season though, the Brazilian was on the move again after having his Juventus contract cancelled by mutual consent. This time he moved to Paris St. Germain – hooking up with his international teammate Neymar Jr – and made an immediate impact by providing an assist for the club’s first goal of 2017/18.
Since then he’s won the Ligue 1 title twice, and has chipped in with 7 assists in both of his seasons at the Parc Des Princes with no real sign of slowing down yet – making him one of the best double free agents in football history.
Defender: Sol Campbell
Perhaps the most controversial entry on this list, England centre-back Sol Campbell first emerged into Premier League action in the early 1990s with Tottenham, whose academy he graduated from after signing with them as a young teenager.
Debuting in 1992, Campbell quickly developed his skills – both quick and imposing, he could tackle hard and dribble the ball out of defence – and cemented himself in the Spurs first team.
By the late 1990s not only was Campbell a key component of the England national team, but he was also Tottenham’s captain, and he led them to their 1999 victory in the League Cup.
However, problems arose when Campbell became disillusioned with the state of Tottenham at the time – the club were miles away from challenging for major honours and couldn’t seem to stick with a manager for long – and allowed his contract to run down.
The defender’s contract ended in the summer of 2001, and despite Spurs offering him a huge contract, he chose to walk away in order to pursue Champions League football – and subsequently signed with Tottenham’s bitter rivals Arsenal, becoming ‘Judas’ to die-hard Spurs fans in the process.
In the end though, Campbell had the last laugh. 2001/02 – his first season with Arsenal – saw him win both the Premier League title and the FA Cup; he won another league title as part of the ‘Invincibles’ side in 2003/04 and while his side eventually came up short, they made the 2005/06 Champions League final against Barcelona and Campbell actually scored Arsenal’s goal in a 2-1 defeat.
Overall, despite making what some considered a questionable move, Campbell was a massive success.
Defender: Markus Babbel
German full-back Markus Babbel was one of the earliest free agent successes of the 21st century, as he actually made his name with Bayern Munich in the mid to late 1990s, winning the Bundesliga on 3 occasions with the Bavarian giants as well as picking up the UEFA Cup in 1995/96 and gaining a Champions League runners-up medal in 1998/99.
Babbel was rumoured to be on his way to the Premier League in 1996, but that never happened and in the summer of 2000, he left Bayern as a free agent and made his way to Liverpool, where he became an integral part of Gerard Houllier’s side, playing largely from the right-back berth.
The German became massively popular with the Anfield crowd for his daring raids down the right flank, and ended up helping the Reds to a unique treble in 2000/01; Liverpool won the FA Cup, the EFL Cup and the UEFA Cup, with Babbel being a particularly key performer in the latter, as he opened the scoring in the final against Alaves after just 4 minutes.
The game turned into a wild affair that Liverpool eventually won 5-4 after extra time, with Babbel playing another part as Magno Mocelin was sent off for a bad foul on him late in the game.
An issue with Guillain-Barre Syndrome largely curtailed Babbel’s Liverpool career – he lost a full season due to the illness and never really came back to form at Anfield – but for the impact he made during his initial season there, he should go down as a great free agent signing.
Midfield: James Milner
One of the Premier League’s most versatile players – able to slot in anywhere in the midfield and also as a full-back at times – James Milner saw success at Newcastle United and Aston Villa before signing for the newly-minted Manchester City in the summer of 2010.
That move was expected to mark the apex of the England international’s career, and indeed, he won two Premier League titles and two FA Cups during his time at the Etihad.
At the end of the 2014/15 season though, Milner’s City career looked dead in the water as he was deemed surplus to requirements, and he ended up making a move as a free agent to Liverpool. Little was expected of his move to Anfield, but instead he’s surprisingly become a huge success for the Reds over the past 4 seasons.
Milner played largely as a midfielder in his early days at Liverpool and was then deployed by Jurgen Klopp as a left-back for almost the entire 2016/17 campaign, performing his duties there excellently too.
2017/18 saw him return to his more familiar midfield role though, and it was from there that he broke the Champions League’s assists record – setting up 9 goals in a single edition of the competition.
Milner has yet to win a trophy with the Reds but it only feels like a matter of time before that changes as Liverpool go from strength to strength, and as the side’s current vice-captain few would play down his importance to Klopp’s side.
Midfield: Andrea Pirlo
Labelled as ‘the signing of the century’ by legendary goalkeeper Gianluigi Buffon, quite how Andrea Pirlo was allowed to sign for Juventus in 2011 as a free agent remains a bit of a mystery, and the club that let him go – AC Milan – probably regret doing it to this day.
At the time of the move Pirlo had won 2 Serie A titles and 2 Champions Leagues with Milan, but after injuries curtailed his 2010/11 season, he was deemed surplus to requirements at the age of just 32.
Pirlo was quickly snapped up by Juventus and deployed as a deep-lying playmaker, his favoured position due to his pace eroding somewhat as his career went on.
Unsurprisingly, any ideas about his decline quickly went out of the window when he helped Juventus to the Serie A title in 2011/12, providing the most assists in the league with 13 and completing a ridiculous 2643 passes with an 87% success rate.
Juventus went on to dominate Italian football with Pirlo in a key role, as he won another 3 consecutive Serie A titles with the Old Lady and was named in the league’s Team of the Season in all of his campaigns at the club, as well as picking up a Ballon d’Or nomination in 2012.
By the time he departed Juventus for New York City in 2015, Pirlo had played 164 games for the club, scoring 19 goals and providing 39 assists, winning 7 trophies and helping them to the Champions League final in 2014/15 too. There’s a clear case in fact for him being the best free agent signing in the history of the game.
Midfield: Paul Pogba
French midfielder Paul Pogba is a strange case in that his move as a free agent came largely before he’d even established himself as a top-level player, but he was such a success following his move that the club he left for free ended up breaking the world record transfer fee to bring him back.
Pogba’s story started in 2009, when he moved to Manchester United’s youth academy from French side Le Havre as a highly touted 16-year old prospect.
Despite some controversy over the move, Pogba was expected to work his way into United’s first team at some point in the future. That never really happened though; despite being promised opportunities by boss Alex Ferguson in 2011/12, and the Frenchman refused a new contract in the summer of 2012.
Instead, he made a move to Juventus as a free agent, and evidently the Italian side believed in him a lot more than United had at that point. He made 27 appearances for Juve in his first season there, winning the Serie A title and earning the Golden Boy award for the best young player in Europe in the process.
From there, Pogba went from strength to strength, becoming a key part of Juventus’ midfield and winning another 3 Serie A titles as well as 2 Coppa Italias. He also helped the team to the 2014/15 Champions League final, although they were unable to beat Barcelona.
By the summer of 2016 his profile had raised so much that United were willing to part with £89m to bring him back to the club – leaving Juventus with a huge profit having signed one of the best free agents of the 21st century.
Midfield: Esteban Cambiasso
Like Dani Alves, Argentine midfielder Esteban Cambiasso made two big moves as a free agent in his career, and like Alves, both of them turned out to be pretty successful.
The defensive midfielder first broke through at Real Madrid in the early 2000s, helping them to win the La Liga title in 2002/03, but by the summer of 2004 – arguably due to Real’s Galactico policy, his contract was allowed to expire, and so he moved as a free agent to Inter Milan.
It was during his time at the San Siro that he saw the most success of his career, as he was partnered with his Argentina teammate Juan Sebastian Veron in the centre of midfield, largely playing a more shielding role.
After starting well in 2004/05, winning the Coppa Italia, Cambiasso became practically an ever-present as the Nerazurri went on a true run of dominance in Italy, winning the Serie A title 5 seasons in a row.
2009/10 was Cambiasso’s crowning moment, though; thriving under boss Jose Mourinho, the Argentine played a key role as Inter surprisingly made their way to the final of the Champions League, eventually winning the trophy by defeating Bayern Munich. 4 more seasons at the San Siro followed before Cambiasso was let go at the age of 34, but his story wasn’t finished there.
Instead, he made another free agent move, this time to Leicester City in a bit of a surprise. But despite his advanced age, Cambiasso proved to be a big hit there too; he helped them to a 14th place finish in his only Premier League season, and left the club in the summer of 2015 after being named their Player of the Year.
Midfield: Sami Khedira
A lot of players on this list were surprisingly let go by their clubs prior to moving as free agents – moves that said clubs may well have lived to regret – but in the case of Sami Khedira, it didn’t really sound like Real Madrid had a choice.
Khedira – a World Cup winner with Germany in 2014 – was apparently offered a huge contract by Los Blancos but chose to leave the Bernabeu to avoid so much stress.
As it turned out, Khedira likely made the right decision. After an injury-hit season in 2014/15 that saw him reduced to just 11 league starts for Real, the summer of 2015 saw him sign a four-year deal with Juventus.
And despite suffering from a handful of nasty injuries in his first season at the Allianz Stadium, he ended up scoring 5 goals – his highest total since 2008/09 – as Juventus won the Serie A title.
Since then Khedira has beaten his best season in terms of goals – scoring 9 in 26 appearances in 2017/18 – and he’s won plenty more trophies at Juventus too, picking up 3 more Serie A titles, 3 Coppa Italias and was a Champions League finalist in 2016/17 – a game that saw his side lose out to his old team Real Madrid.
Khedira is now slowing down somewhat at the age of 32 – he made just 10 league appearances in 2018/19 in another injury-curtailed season and was recently cut from the German national squad – but it’d be hard to label his time at Juventus as anything but a success – his all-action midfield style has helped Juventus massively over the last few years.
Striker: Zlatan Ibrahimovic
When you take into account cumulative transfer fees, Swedish striker Zlatan Ibrahimovic is up there with the most expensive players in the history of football. Plying his trade at huge clubs like AC Milan, Barcelona and Paris St. Germain, by 2016 he’d won titles in Spain, France, Italy and the Netherlands – and only a stint in the Premier League seemed missing from his ledger.
Even so, despite such a great and extensive record, a lot of fans were still cynical when Ibrahimovic signed for Manchester United as a free agent in the summer of 2016. It felt like a classic United vanity signing, but as it turned out, Zlatan more than lived up to his end of the bargain and had one of the best seasons of his career, taking the Premier League by storm.
Wasting no time, Ibrahimovic scored on his United debut as the Red Devils defeated Leicester to win the Community Shield, and then he found the back of the net in his Premier League debut in a game against Bournemouth too.
By February, the Swede already had 15 Premier League goals to his name – becoming the oldest player to score at least 15 goals in the competition at 35 years and 125 days old.
In the end, Ibrahimovic went on to score the goals that won United the EFL Cup, and then won the Europa League with them too, although he didn’t appear in the final due to a knee injury.
Even the injury became a plus point for him, as he refused to take a wage from United while he was out – quietening a lot of detractors in the process. He might not have led United to the Premier League title, but as a free agent signing, he was a huge hit.
Striker: Robert Lewandowski
One of the more controversial moves on this list – in a similar vein to Sol Campbell’s move from Tottenham to their bitter rivals Arsenal – Polish striker Robert Lewandowski made the move from Borussia Dortmund to Germany’s bigger, more successful club Bayern Munich in 2014, and while he’s gone onto massive success, it’s not hard to see why Dortmund fans would be bitter.
Lewandowski had become a legend at the club over 4 seasons; after somewhat of a slow start in 2010/11, he averaged 31 goals a season in the subsequent 3 and won two Bundesliga titles, as well as helping Dortmund to the final of the 2012/13 Champions League – where his side were coincidentally defeated by Bayern.
However, Lewandowski ended up in a dispute with Dortmund’s board with regards to his wages – which he felt were too low – in late 2013 and ended up signing a pre-contract with Bayern in January 2014 with the full transfer to take place that summer. Dortmund fans were so angry that they even stole the tyres from Lewandowski’s car.
In the end though, the Polish striker has had the last laugh. In his 5 seasons at the Allianz Arena he’s won 5 Bundesliga titles and 2 DFB-Pokals, and has averaged an astonishing 38 goals per season – winning the award for the league’s top goalscorer on 3 occasions.
He’s become a Bayern legend and has become the Bundesliga’s all-time leading foreign goalscorer – the very definition of a hugely successful free agent signing.
