The free transfers that left a bad taste

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By Football Tripper
Last Updated: December 16, 2021


Diego Costa, Jérôme Boateng, and as of recently Lionel Messi. All are currently free agents and yet to find a club for next season.

In a recent Football Tripper article, we delved into our top three free agent signings of all time. It won’t come as a surprise if Messi writes himself onto that list in the coming years. At a tearful news conference he said goodbye to the catalonian club he’s made history with for 21 years. Paris St Germain is the likely destination for the Argentinian.

Wherever he ends up, one thing is for certain. There will be great expectations of the six time ballon d’or winner.

And this got us thinking… What if the unthinkable happens and he’s not a success for his new club? Because just like online betting it isn’t a sure thing – even if it’s Lionel Messi we’re talking about. (Although we’d put a healthy wager on that he will be.)

Thankfully it won’t be long until we find out. But before then, we thought we’d take a dive through the history books and single out three players who signed on a free where it didn’t quite work out as well as everyone had hoped.

Our top 3 worst free transfers:

  1. Nicolas Anelka. Shanghai Shenhua to West Bromwich Albion.
    Anelka seemed like a dream signing for the Baggies at the time. At 34, incidentally the current age of Messi, Anelka was well regarded on the pitch. Although he’d definitely seen his fair share of controversy. At Real Madrid his attitude came into question. He played well for Arsenal and Liverpool but both sets of fans felt he was only loyal to himself. The Frenchman was sent home during the 2010 World Cup after a bust up with the manager Raymond Domenech. Unfortunately it was this controversial player West Brom signed. He played 12 games for the Baggies. During that time he fell out with manager Steve Clarke and didn’t get much game time. After Clarke got sacked, Anelka did score 2 goals but celebrated one with a controversial salute that had links to anti-semitism. The FA banned and fined him because of it. Later Anelka claimed that the salute was misunderstood and a protest directed at previous manager Clarke. Shortly after this suspension he informed the world via social media he was leaving West Brom, which was the first the club had heard of it! So West Brom told the world themselves they would be sacking Anelka. Football drama at its best.

  2. Joe Cole. Chelsea to Liverpool.
    Joe Cole was 29 when he signed for Liverpool which is pretty damn close to a footballer’s ‘prime years’. With Chelsea he had won the Premier League three times, the FA Cup twice and the Football League Cup & Community Shield once respectively. Many Chelsea fans wanted him to stay. He’d also had some golden moments in an England shirt, most memorably producing a magical performance against Sweden in the 2006 World Cup. Liverpool fans were excited. But this excitement quickly evaporated when Cole was sent off in Liverpool’s season opening game. Thereafter he started only 9 games before being loaned to Lille. He did return to Liverpool afterwards but could never quite prove his worth, eventually being sold to West Ham in 2013.

  3. Mark Bosnich. Manchester United to Chelsea.
    Bosnich was never a football star but he’s definitely worth mentioning when talking about free transfers that didn’t go well. There’s two things you need to know about the Australian goalkeeper. Firstly, he’s the only player Alex Fergurson signed twice. Secondly, his time playing in England was brought to a close when Chelsea sacked him after testing positive for cocaine use. What could’ve been a great free transfer for Chelsea, providing some great competition for who would start in goal for them, turned into a nightmare. Fergurson, despite rating Bosnich’s talent, labelled him a ‘terrible professional’ and was ultimately vindicated after he let him leave for Chelsea on a free.


Notable mentions for worst free transfers

Marouane Chamakh (FCCB > Ars) Jose Bosingwa (Che > Qpr) Robert Pires (Vcf > Avfc) Milan Jovanovic (Che > Liv)

Football Tripper Logo

By Football Tripper
Last Updated: December 16, 2021