The 2023-24 winter transfer window is in session and the market is buzzing with juicy rumors. Premier League giants Arsenal have been heavily linked with Brentford ace Ivan Toney, Chelsea are reportedly eyeing a move for Napoli sharpshooter Victor Osimhen, and Manchester United star Jadon Sancho is supposedly on his way back to Borussia Dortmund after his public fallout with manager Erik ten Hag. Real Madrid, Liverpool, and Bayern Munich have also generated their fair share of rumors over the past few weeks.
As we navigate through the whirlwind January transfer window, let us take a look at some of the biggest deals that have materialized in this period over the years. Continue reading to check out the most expensive winter transfers in history:
#10 Diego Costa (Chelsea to Atletico Madrid): €60 million ($65.59 million)
One of the most formidable strikers of this generation, Diego Costa left Chelsea for Atletico Madrid for a €60 million ($65.59 million) fee in January 2018. He spent the next three years of his career at Atletico, scoring 19 goals and providing 14 assists in 81 games across competitions.
Before returning to the Spanish capital, Costa netted 59 times in 120 games for the Blues in all competitions, helping them to two Premier League titles and one Carabao Cup.
#9 Pierre-Emerick Aubameyang (Borussia Dortmund to Arsenal): €63.75 million ($69.69 million)
Jet-heeled center-forward Pierre-Emerick Aubameyang brought a lot of optimism when he moved to Arsenal from Borussia Dortmund in January 2018. The Gunners paid a handsome €63.75 million ($69.69 million) to acquire his services, which ultimately turned out to be a smart investment. Barring his controversial exit in January 2022, the Gabonese attacker had a successful run at Arsenal, scoring 92 goals and providing 21 assists in 163 games across tournaments.
The former Gunners captain, who scored 141 goals in 213 games for Dortmund between 2013 and 2018, won one FA Cup and one FA Community Shield during his stay in north London.
#8 Christian Pulisic (Borussia Dortmund to Chelsea): €64 million ($69.96 million)
In January 2019, Chelsea brought USMNT international Christian Pulisic to Stamford Bridge. The Blues splurged €64 million ($69.96 million) on the player, who had scored 19 goals and provided 26 assists in 127 games for his boyhood club Borussia Dortmund.
Unfortunately, the 25-year-old could not live up to his price tag in London, only impressing in bits and pieces. Before joining AC Milan permanently in July 2023, Pulisic played 145 games for the Pensioners, recording 26 goals and 21 assists.
#7 Aymeric Laporte (Athletic Bilbao to Manchester City): €65 million ($71.06 million)
Premier League holders Manchester City splurged €65 million ($71.06 million) to sign Aymeric Laporte from Athletic Bilbao in January 2018. The Spanish center-back, who scored 10 goals in 222 games for Bilbao in six seasons, proved to be worth the price tag, as he produced numerous top-drawer performances before leaving City for Al-Nassr in August 2023.
The 29-year-old played 180 games for the Mancunians, scoring 12 times and providing four assists. His bravado at the back helped Pep Guardiola’s team to 15 trophies, including five Premier League titles and a UEFA Champions League.
#6 Bruno Fernandes (Sporting CP to Manchester United): €65 million ($71.06 million)
Manchester United captain Bruno Fernandes moved to Old Trafford from Sporting CP in January 2020. The Red Devils paid a cool €65 million ($71.06 million) for the Portuguese, and it is safe to say that he has done more than enough to do justice to his lofty price tag.
The Portugal international has easily been United’s standout performer in the last four years. He has popped up with important goals and assists time and again, securing crucial points for the 20-time English champions. Since January 2020, Fernandes has played 212 games for United in all competitions, scoring 70 goals and providing 59 assists, helping them to the Carabao Cup in 2023.
#5 Mykhailo Mudryk (Shakhtar Donetsk to Chelsea): €70 million ($76.52 million)
Chelsea spent a whopping €70 million ($76.52 million) to sign Mykhailo Mudryk from Shakhtar Donetsk in January 2023. Unlike most players on this list, the Ukrainian had not done enough at his former club to justify such a massive price tag. The left-winger scored 12 goals and provided 17 assists for Shakhtar in 44 games before sealing his big-money move to Stamford Bridge.
Mudryk has gotten a lot of flak for his performances since switching to England last winter. He has yet to attain consistency, with him scoring just four times and providing four assists in 38 games for the Pensioners across tournaments.
#4 Dusan Vlahovic (Fiorentina to Juventus): €83.5 million ($91.28 million)
In fourth place, we have Serbian hitman Dusan Vlahovic, who became the most expensive winter transfer in Serie A history when he joined Juventus from Fiorentina for a €83.5 million ($91.28 million) fee in January 2022. Vlahovic sealed the move courtesy of his excellent return of 49 goals in 108 games for La Viola in two-and-a-half seasons.
Vlahovic has not yet lived up to his price tag, but the Bianconeri are backing him to turn his fortunes around. The 23-year-old has played 81 matches for the Old Lady, bagging 30 goals and eight assists.
#3 Virgil van Dijk (Southampton to Liverpool): €84.65 million ($92.54 million)
Easily the most successful player on this list, Virgil van Dijk became the most expensive defender in Premier League history when he moved from Southampton to Liverpool for a massive €84.65 million ($92.54 million) fee in January 2018. The Dutchman hit the ground running at Anfield, helping the Reds to the UEFA Champions League final in his debut season. In the next two seasons (2018-19, 2019-20), Liverpool won their sixth UEFA Champions League and their 19th Premier League title, with Van Dijk emerging as one of their best performers in both campaigns.
Over the last six years, the world-class center-back has played 242 games for the Anfield outfit, scoring 20 times and providing 14 assists.
#2 Enzo Fernandez (Benfica to Chelsea): €121 million ($132.28 million)
Chelsea seem to have a love affair with the winter window, with them completing three massive transfers in that period over the years.
Mykhailo Mudryk was not the Blues’ only big-ticket purchase in January 2023, they also added 2022 FIFA World Cup winner Enzo Fernandez to their ranks. Chelsea splurged an eye-popping €121 million ($132.28 million) on the Argentine last winter, making him the most expensive winter signing in Premier League history.
Like Mudryk, Fernandez has also not been at his best at Stamford Bridge. The highly-rated central midfielder has scored four times and provided three assists in 45 games for Mauricio Pochettino’s side across competitions.
#1 Philippe Coutinho (Liverpool to Barcelona): €135 million ($147.58 million)
Arguably the worst transfer in Barcelona’s history, Philippe Coutinho moved to Camp Nou from Liverpool for a mind-numbing €135 million ($147.58 million) fee in January 2018. The Brazilian attacking midfielder had enjoyed an excellent spell at Anfield, scoring 54 goals and claiming 45 assists in 201 games for the club in all competitions. Unfortunately, he could not carry his wizardry over to Spain.
Before selling him to Aston Villa for just €20 million ($21.86 million) in July 2022, Barcelona sent him out on a couple of loan spells; first to Bayern Munich and then to Villa. Coutinho won the UEFA Champions League with Bayern in the 2019-20 season, scoring twice en route to the Bavarians’ historic win over the Blaugrana in the quarter-finals.
Overall, Coutinho played 106 games for the Catalans, scoring 25 times and providing 14 assists.
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