Deadline day is always the most dramatic day in every transfer window. The adrenaline rush that comes with hurrying to complete signings before time elapses always seems to leave clubs, players, and fans at the edge of their seats. We’ve seen some really amazing deals get completed on the very last day of the transfer window like Wayne Rooney to United, Luis Suárez to Liverpool, and Pierre-Emrick Aubameyang to Arsenal, but today, we’re not here to talk about the good; we’re here for the downright horrible!
These are the 7 worst deadline day signings in football history. There’s a Ballon d’Or winner on this list. Can you guess who it is?
Give us your guesses in the comments, we’ll see if you’re right later in the video. Anyway, let’s start with the most infamous of the lot – Fernando Torres to Chelsea. On deadline day of the 2011 January transfer window, Chelsea completed the shocking signing of Fernando Torres from Liverpool, making him the 6th most expensive player in the world and the most expensive signing ever made by an English club at the time.
Looking at how good he was for Liverpool, everyone thought he would be amazing for Chelsea, as well, but it turned out to be the exact opposite. Torres’ time at Chelsea was a horrorshow. The man was a shadow of himself, finding it so hard to find the back of the net, and worse still, often missing open goals.
He was never able to really salvage his reputation after his time at Chelsea, and it continues to haunt him to this day. At least, he got a Champions League and Europa League for his troubles. Now, Torres leaving Liverpool on deadline day in January 2011 forced the Reds to quickly look for a replacement that same day, and you know who they chose?
Andy Carroll. They paid 30 million pounds for him, making him the 8th most expensive footballer in the world and the most expensive British footballer ever at the time. Things didn’t start well for him at Liverpool.
His debut was delayed because of an injury, and when he eventually started to play, it turned out to not be worth the wait. Carroll ended up scoring just 11 goals in 58 appearances for Liverpool, and just a year and half after signing him, the club decided to cut their losses and get rid of him. Another truly horrible deadline day signing was that of Robinho by Manchester City in the summer of 2008.
Abu Dhabi United Group completed the takeover of Man City on transfer deadline day in 2008, and that same day, they signed Robinho for 43 million euros from Real Madrid. And what’s funny is that the Brazilian was actually on his way to Chelsea that summer, but City came and hijacked the deal. We’re sure they now wish they had just let him go to London because he turned out to be a huge flop.
To be fair, his first season was decent, but after that, it was downhill. He was out for 3 months due to injury, and after that he wasn’t able to hit those heights again. So, halfway into his second season, he went back to Brazil, moving to Santos on loan, before then joining AC Milan permanently at the end of the season.
Man City spent heavily on Robinho because they thought he would be a marquee signing – a statement of purpose from the new owners – but he ended up flopping criminally and they just had to hold the L. On the other side of Manchester, meanwhile, they had to hold their own L after they signed Radamel Falcao on the last day of the 2014 summer transfer window and he turned out to be a flop. They paid 6 million pounds to get him on loan from Monaco with an option to buy at the end of the season.
Yes, it was only a loan deal, but he was put on 265k pounds per week, so it was actually a huge investment, especially back then in 2014. The Colombian striker ended up scoring just 4 goals for Man United that season, even suffering a demotion to the under-21s at some point in the season. He was labeled one of the worst signings of the season, and exercising the option to buy was not even considered at Old Trafford.
Up next is another striker Martin Braithwaite. Espanyol signed him on deadline day of the 2022 summer transfer window, and it ended up being really messy. Braithwaite terminated his contract with Barcelona in 2022 which allowed him to join Espanyol for free, but he was not able to help them survive relegation that season, and this was where the drama started.
Braithwaite said he didn’t want to play in the second tier and he began to do everything possible to force a move out of the club. When all failed, he reluctantly stayed for one season before then terminating his contract and moving to Brazil to join Grêmio in 2024. The Danish attacker couldn’t save Espanyol from relegation and then went on to anger the club and the fans by acting like he was too big for the second division.
Even though he was free, we’re pretty sure he is one signing that Espanyol really regret making. The fact that he came from their bitter city rivals surely didn’t make the pill any easier to swallow. Now, remember we told you that there’s a Ballon d’Or winner in this video.
Did you guess Cristiano Ronaldo? If you did, then you’re very…wrong! It is actually Michael Owen.
The Englishman moved from Real Madrid to Newcastle for a then-club record fee of 16. 8 million pounds, but things started out badly for him after he suffered an injury in preseason which ruled him out for the first couple months of the new season. He would then suffer another injury in December which ruled him out until April 2006.
But that was just the beginning. At the 2006 World Cup, he tore his ACL in a group stage game against Sweden, which sidelined him until April 2007. Injuries kept plaguing the Ballon d’Or winner, which caused him to miss a lot of games.
He ended up scoring just 30 goals for Newcastle in 4 years, an average of less than 8 goals a season. Obviously, it was not his fault, but the truth is that Michael Owen was a bad investment for Newcastle United, especially at a club record fee. To make matters worse, Newcastle ended up suffering relegation in Owen’s final season at the club.
He then left on a free and joined Man United where he won the Premier League while Newcastle were banished to the Championship. That must have stung if you are a Newcastle fan. Finally, we have Owen Hargreaves.
The year was 2011 and Patrice Vieira had just retired, so Man City were looking for a replacement. They also needed a player who would play in the midfield while Yaya Touré would be off to the AFCON halfway into the season. They tried to get van Bommel, De Rossi, and Gago, but they couldn’t, so they ended up signing Owen Hargreaves on deadline day for free following the expiration of his contract with Manchester United, hijacking the transfer from West Brom.
Anyway, it turned out to be a bad signing; for him more than for the club, if we’re being honest. First of all, he was not included in Man City’s Champions League squad that season and then he ended up not being used in the Premier League. He made only one Premier League appearance, so even though Man City won their first Premier League that season, he didn’t receive a winner’s medal.
Hargreaves ended up being released from the club after just one season and four appearances, and he would end up retiring that year at the relatively young age of 31. Of course, there are more deadline day deals that have been really bad, like Benni McCarthy to West Ham, André Santos to Arsenal, and Xisco to Newcastle. Can you think of more bad deadline day signings?
Feel free to drop their names in the comments. Also, which of the deadline day transfers that got completed this year do you think will end up being horrible in a year or two? Tell us in the comments.
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