13) Andy Cole for Keith Gillespie
Newcastle’s hopes of toppling Manchester United after finishing second a season before they took a heavy blow when the Red Devils signed Andy Cole from them. The striker had been in prolific form, scoring a massive 34 goals in just 40 games in the season before. Keith Gillespie went the other way in the deal. While Cole enjoyed great success with United, winning five league titles, Newcastle failed to rebuild after their star striker’s departure. Gillespie spent three and a half years at Saint James’ Park.
12) Roberto Carlos for Ivan Zamorano
Ivan Zamorano was the star behind Real Madrid’s La Liga title back in ’95, scoring 28 goals in 38 games. His superb form earned him a move to Inter Milan as then-manager, Roy Hodgson, allowed Roberto Carlos to move to Madrid as a part of the deal. Carlos went on to become the greatest left back the game had ever seen.
11) Christian Vieri for Diego Simeone
Chrisitan Vieri’s transfer to Inter back in ’99 was a world record at the time. The deal also involved Diego Simeone, the current Atletico boss, moving to Lazio in exchange. While Vieri was always potent for Inter scoring 103 goals in six seasons, major honours eluded him. The same cannot be said for Simeone and Lazio, as the club won the double in ’00, defeating Inter in the final of the Coppa Italia.
10) Andrea Pirlo for Andres Guglielminpietro
One of the biggest transfer blunders of all time, Inter allowed Andrea Pirlo to move to AC Milan in the summer of ’01, in a deal which brought Guglielmipietro to the blue part of Milan. While the Argentine failed to do anything spectacular at Inter, Andrea Pirlo became the greatest deep-lying playmaker of all time at AC Milan. Pirlo became the cornerstone of Milan’s success under Ancelloti, before completing a controversial move to rivals Juventus.
9) Clarence Seedorf for Francesco Coco
Inter failed to learn from their mistake of letting Pirlo leave, as they allowed Seedorf to move to AC Milan bringing left-back Coco to Inter. As Coco failed to get in the starting eleven for Inter, Seedorf joined Pirlo, Gattuso and Kaka to complete one of the most ferocious and dynamic midfield ever seen in the game before as Milan won every major honour on offer.
8) Fabio Cannavaro for Fabian Carini
Fabio Cannavaro joined Juventus from Inter after two largely successful years in Milan. The deal also involved the transfer of Juve’s reserve goalkeeper, Carini to the other side. Cannavaro reunited with Buffon and Thuram, as Juve won two Serie A titles, both of which were cancelled due to the Calciopoli scandal. On the other hand, Carini, who was supposed to be at the heart of the rebuilding project, struggled to make any impact making just four appearances in three seasons.
7) Michael Owen for Antonio Nunez
Real Madrid signed Michael Owen in the summer of ’04, in a deal that saw Antonio Nunez move the other side. Owen, a Ballon d’Or winner in 2001, was used in a relegated role, often coming on from the bench. The striker ended his stay in Madrid after just one season, scoring 13 goals in 36 games. He joined Newcastle United, whereas Nunez struggled to get in the Liverpool side. His time at Merseyside too lasted just a year as he returned to Spain to play for Celta.
6) Ashley Cole for William Gallas
One of the most controversial transfers of all time, Cole angered sections of Arsenal supporters with his decision to join rivals, Chelsea. The left back had continuously flirted with the idea of playing for Chelsea, a move that saw many fans deride him as ‘Cashley’. Cole won every possible trophy with Chelsea during his time before leaving for Roma after nearly a decade with Chelsea. Gallas, on the other hand, became a problem for Arsenal due to his attitude and conflicts with the teammates.
5) Jose Antonio Reyes for Julio Baptista
The two players swapped their clubs in ’06 after successful seasons with Real Madrid and Arsenal. Reyes had won the La Liga title with Real Madrid, whereas, Baptista was on the losing side of the cup final with Arsenal. The loan move for both players failed to work out as Reyes was sold to Atletico a season later, while Baptista joined Roma in ’08.
4) Zlatan Ibrahimovic for Samuel Eto’o
The summer of ’09 saw two of the world’s most prolific striker swap their clubs as Ibrahimovic joined Barca from Inter whereas Eto’o moved to Inter having won the treble with Barca. Ibrahimovic, though, soon fell out with Pep Guardiola and left the club after just one season. Eto’o became a prominent member of Mourinho’s side as the Italians won the elusive treble, defeating Barca on their way to European glory.
3) Diego Milito for Robert Acquafresca
Thiago Motta for Francesco Bolzoni
Inter and Genoa struck a double swap deal in ’09, that saw Milito and Motta move to Inter while Genoa got Acquafresca, Bolzoni and academy players in return. Milito and Motta enjoyed the time of their life in San Siro as Inter won the treble. Milito scored a brace in the Champions League final of ’10, earning a Ballon D’Or nomination, while Motta became the leader for Mourinho’s men.
2) David Luiz for Nemanja Matic
Over the years, Benfica have made a name for producing and nurturing some of the best talents before selling them to top European clubs. The magnificent list includes the likes of David Luiz, Di Maria, Ramires and more recently, Renato Sanchez. One of their talents, David Luiz, was sold to Chelsea in a swap deal, which involved Nemanja Matic move to Estadio Da Luz. As Luiz won the Champions League title with Chelsea, Jorge Jesus developed Matic into an excellent holding midfielder, who would return to Chelsea two and a half years later, and win two premier league titles with the Blues.
1) Fernando Torres for Alessio Cerci
After a failed spell at Chelsea, Torres joined AC Milan in order to resurrect his career. However, Torres failed to settle in Italy and soon returned to his boyhood club, Atletico Madrid. The Spaniard may not be the same player who terrorised top defences but is still a handy option to bring on from the bench. Cerci, on the other hand, returned to Milan after a miserable six months at Madrid. Cerci has since seen his growth decline massively with failed loan spells in Milan and then Genoa. His permanent move to Verona was confirmed this summer.