Football Features

From Zlatan Ibrahimovic to Michael Owen, 11 players who timed their transfer moves badly

By Muhammad Butt

Published: 14:00, 26 June 2022

Some players make their transfer moves at the right time, joining or propelling a team to greater heights. Others… don’t.

Sometimes players just get it all wrong and join a rapidly ending party, a sinking ship, a decaying empire. Sometimes the players themselves make it worse, sometimes they just have terrible timing.

We’ve had a look at some of those players who just made their transfer moves at the worst possible time.

Hakan Calhanoglu: AC Milan to Inter Milan, 2021

Hakan Calhanoglu’s AC Milan contract was expiring at the end of the 2020/21 season and he had just seen his Milan side capitulate the Serie A title to Antonio Conte’s dominant Inter. It looked to be the start of a Nerazzuri era, so naturally Calhanoglu jumped ship, for free!

Fast forward one year and Antonio Conte is gone, Inter are confirmed to have to sell a superstar a season, Romelu Lukaku is returning to Inter with his tail between his legs after a humbling season in England and, oh yeah, AC Milan just beat Inter Milan to win Serie A with Zlatan Ibrahimovic and other Milan players mocking Calhanoglu during their title celebrations.

Antoine Griezmann: Atlético Madrid to Barcelona, 2019

When Antoine Griezmann joined Barcelona, the Blaugrana had just won two straight league titles under Ernesto Valverde. They were missing a little something, and the world-class Griezmann was meant to be that something.

Instead Griezmann arrived into a team that was losing its way stylistically and, with Luis Suárez’s declining physical profile, losing its bite up-front. Griezmann squeezed himself into a left-wing role and never looked close to recapturing his brilliant Atleti form as Barcelona wilted into nonsensical irrelevance, ending his first season with a devastating 8-2 loss to Bayern Munich.

Griezmann stayed in Barcelona for just two seasons, winning only the Copa del Rey. He was a full participant in the club’s “banter era” and left at the start of 2021/22, just a couple of months before Xavi and Mateu Alemany got the club back on the path to greatness.

Wendel: Sporting to Zenit St. Petersburg, 2020

Back in the summer of 2020, Sporting CP had not won the Primeira Liga since 2001/02. Wendel had been with Sporting for three seasons at the time and with no signs of success, he joined Zenit St. Petersburg.

Of course, the following season Sporting powered their way to win the Primeira Liga with a wonderfully dominant showing, spending 29 of the 34 gameweeks atop the table to secure their first title in 18 years.

Sure, Wendel has won the Russian Premier League twice with Zenit, but they had won it two years before he joined too. It’s a standard victory, nothing like the sheer ecstasy of ending a near two-decade title drought.

Emre Can: Liverpool to Juventus, 2018

Emre Can was a useful part of Jurgen Klopp’s growing Liverpool side. He was there when Mohamed Salah and Virgil van Dijk joined and while he missed much of the run-in with a back injury, he clocked up 2,942 minutes over the full season as Liverpool finished fourth and lost the Champions League final to Real Madrid (he played 7 minutes off the bench).

Seeking a greater chance to win, Can joined Juventus that summer on a free transfer having rejected Liverpool’s renewal offers. Of course Liverpool evolved into one of the very best teams in the world the following season, returning to the Champions League final and emerging victorious. The next season they ended a 30 year wait for a league title win too while Can, having disappointed in his first season with Juve, was left out of their Champions League squad, spent half a season on the bench then got loaned out to Borussia Dortmund. Oh dear!


Summer transfer odds 22/23: To sign for before 3rd September Sky Bet
Cristiano Ronaldo to Sporting CP 5/1
Antony to Man Utd 8/13
Christian Pulisic to Newcastle 6/1
Frenkie de Jong to Man Utd 5/2
Youri Tielemans to Arsenal 10/11
Pierre-Emerick Aubameyang to Chelsea 2/7
You have to be 18+ to gamble. UK only. All odds within this article are accurate at the time of writing (14:00, 19/08/2022). Be Gamble Aware.

Anthony Knockaert: Leicester to Standard Liege, 2015

Anthony Knockaert joined Leicester in the Championship on a three year contract and ran the gamut of experiences. The most dramatic failed promotion in 2013, actual promotion in 2014, and then late Premier League survival in 2015.

He was given a new contract offer but rejected it, opting to join Standard Liege in Belgium for a greater chance at first-team minutes. Of course the very next season Leicester went on to perform the miracle of miracles, winning the Premier League title. Missing out on that after all he had already been through? Excruciatingly bad timing!

Martin Odegaard: Stromsgodset to Real Madrid, 2015

When Martin Odegaard was 15 years old he was such a sought-after prospect he toured all of Europe’s best clubs to decide where to head next, deciding on European champions Real Madrid. Of course, this was a terrible decision for Odegaard’s personal development.

Real Madrid have never lacked for trophies but their development of young players has always been suspect and Odegaard absolutely wrecked key years of his development trying to make it in a place not set-up to help him make it.

Loans to the Eredivisie and Real Sociedad helped him rebuild himself, but the spark of world conquering genius he had faded away, which is why he’s now playing (very well) for Arsenal instead of one of the world’s elite.

Diego Costa: Brazil to Spain, 2014

Diego Costa was born and raised in Brazil but had felt disrespected by the Brazilian national team. Having played in Spain for a number of years he qualified for Spanish citizenship, and so made the switch just before the 2014 World Cup.

At the time Spain had won the last three major international tournaments and a striker like Costa was all that the squad seemed to be missing. Of course the midfield that had been so key to Spain’s dominance was in decline, and as a result the 2014 World Cup was a moment of horrifying humiliation as Spain were turfed out in the group stages.

All told Costa played just 24 times for Spain, scoring 10 goals. His period in the side coincided with Spain’s low ebb and he ended up winning nothing while Brazil, with a striker like him, could have tasted international glory. Whoops.

Sergio Canales: Racing to Real Madrid, 2010

Sergio Canales was one of the hottest prospects in Spanish football, one of the very best teenagers you will have ever seen. A player of such beguiling brilliance that Real Madrid signed him after just half a season of starting in La Liga, picking him up in January 2010 amid interest from other clubs all around Europe.

Of course Real Madrid is not a club to develop youngsters, especially as in the summer of 2010 they replaced the lovely Manuel Pellegrini with the ruthless José Mourinho. Canales barely played and was turfed out on loan to chaos merchants Valencia where horrendous structure and awful luck with injuries devastated his career.

Canales slowly rebuilt himself at Real Sociedad and later Real Betis, and is now at 31 years-old one of the most exciting players in La Liga. But he should have been doing this for the whole decade, if only he had made the right call back then!

Zlatan Ibrahimovic: Inter to Barcelona, 2009

In 2008/09 Pep Guardiola’s Barcelona revolutionised all of football with their majestic style of play and astounding tactical intelligence. To this electric chemistry they added a gigantic world-class no. 9 in Zlatan Ibrahimovic. A match made in heaven, right?

On the pitch, sure, but off the pitch Ibrahimovic couldn’t handle Messi being the star of the side and the Swede’s form waned severely in the second-half of the season and what looked like a second consecutive Treble turned into a La Liga win and nothing else.

To make matters worse? Inter regrouped in his absence and won the Treble themselves, beating Barcelona along the way! And when Zlatan left Barcelona after just one season, the Blaugrana reclaimed the Champions League straight away!


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Andriy Shevchenko: AC Milan to Chelsea, 2006

Chelsea’s then-owner Roman Abramovich loved Andriy Shevchenko and tried to sign him in the summer of 2005. Failing there, he came back the next year and got his man. For Sheva’s part he was joining the two-time champions of England, a monstrous side looking to become champions of Europe.

Yet Sheva joined them just as Sir Alex Ferguson’s Manchester United were rising. Built around a young core, the Red Devils ripped the title out of Chelsea’s hands for both of Shevchenko’s seasons in England, even beating the Blues in the 2008 Champions League final as Shevchenko watched on as an unused substitute.

Michael Owen: Liverpool to Real Madrid, 2004

Back in the early 2000’s, Real Madrid signed a Galactico every summer. 2000 was Figo, 2001 was Zinedine Zidane, 2002 was Ronaldo, 2003 was David Beckham. All of them were beloved by fans and successful on the field. 2004 saw Michael Owen join the club and he was literally the most pointless Galactico ever. Not only did Madrid not need another striker, but they desperately needed defensive cover instead.

Owen spent at least half of his season in Madrid coming off the bench, and even scoring in a Clásico win wasn’t enough to convince the club he was worth a damn. Owen retreated to the Premier League after just one season, leaving behind him a decaying Madrid side who went three straight seasons without a trophy as Barcelona dominated La Liga and Europe.

But the real dagger for Owen? He left Liverpool primarily for a greater chance at winning the Champions League, and with three wins in the previous seven seasons, Madrid seemed a great bet. Well, that obviously didn’t happen. What did happen, of course, was Rafa Benitez guiding Liverpool to the most ridiculous and improbable Champions League in 2004/05, beating Juventus on the way – the same Juventus that turfed Owen’s Madrid out while the Englishman played just 44 minutes in the tie.

Owen left after just one season, while David Beckham kept on plugging away and was rewarded as Madrid won La Liga back from Barcelona in 2006/07 while Owen, suffering from injury due to the excessive physicality of the Premier League, played just three games.

Hideous timing all around.

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