Coutinho, Cannavaro, Pirlo & Inter’s craziest ever sales

Dennis Bergkamp was arguably the hottest prospect in world football when he joined Inter from Ajax in 1993. 

However, the Dutchman forward struggled to both score goals and come to terms with the demanding nature of the Italian press, resulting in one paper renaming their 'Donkey of the Week' award 'Bergkamp of the Week'.

The Netherlands ace felt the Nerazzurri were to blame for his poor return, claiming, "They said: 'We're going to play more offensive.' And they did, but only for the first month!"

As a result, Bergkamp was only too happy to leave when Arsenal came calling in 1995. 

Inter got £7.5 million for the striker but that proved scant consolation as Bergkamp became an icon in north London by rediscovering his goalscoring touch and, more importantly, wowing the English game with his wondrous ball control.

Nobody would question the wisdom of Inter's decision to sign Thiago Motta and Diego Milito from Genoa in 2009.

However, the Nerazzurri erred badly during the negotiations by agreeing to sell Leonardo Bonucci to the Rossoblu for just €4 million. 

The then 22-year-old was coming off the back of an impressive six-month loan spell at Pisa, where coach Gian Piero Ventura had quickly realised Bonucci was a special breed: "He's a centre-half who thinks like a midfielder."

As a result, Ventura was delighted when his new club Bari snapped up Bonucci before he'd even played a game for Genoa. 

Bonucci excelled once again under the future Italy coach and, inside a year, he had joined Juventus for €15.5m.

The 31-year-old has since proven himself one of the finest ball-playing centre-halves in the world, much to the embarrassment of Inter.

Exactly why Inter felt compelled to swap Fabio Cannavaro for Juventus goalkeeper Fabian Carini in 2004 remains shrouded in mystery.

It has even been claimed that former Bianconeri director Luciano Moggi told Cannavaro to feign injury in order to persuade the Nerazzurri to cut their losses on the centre-half, who had disappointed in the two seasons that followed his €23m transfer from Parma. 

However, that story doesn't really explain why Inter felt Carini, who had spent the previous two seasons on loan at Standard Liege, was worth €10m, as much as Cannavaro. It remains one of the most bizarre valuations in football history and former president Massimo Moratti has never lived it down.

Of course, Cannavaro, who has always insisted that Inter "wanted Carini at all costs", went on to prove himself the best centre-half in the world, winning the World Cup in 2006 before leaving for Real Madrid after Juve were relegated from Serie A for their involvement in Calciopoli.

As for Carini, the Uruguayan made just four appearances for Inter before being allowed to join Murcia in 2007.

Roberto Carlos has long blamed one man and one man alone for Inter's ludicrous decision to sell him to Real Madrid in 1996 for just €6m.

“It's not that I did not have a good relationship with Roy Hodgson," the Brazilian said of the former Nerazzurri coach. "It is just that Hodgson doesn't know much about football."

The former England manager wanted Roberto Carlos to play as a winger but the thunder-thighed South American only felt comfortable at left-back, where he was first-choice for the Selecao.

"I spoke to (Inter president) Massimo Moratti to see if he could sort things out and it soon became clear that the only solution was to leave," he revealed.

So, Roberto Carlos joined Real Madrid, where he would spend the next 11 years proving himself one of the greatest left-backs of all time.

Inter president Massimo Moratti defended his decision to sell Philippe Coutino to Liverpool in 2013 by saying, "I think it could be a great opportunity for Coutinho and a deal that might work out well for us."

He was half-right, in fairness. It was indeed a great opportunity for Coutinho, one he fully exploited, with the Brazilian going on to prove himself one of the best attackers in the world at Anfield.

It did not work out well at all for Inter, though.

They off-loaded a player that Moratti himself had previously described as "the future of Inter" for just £8.5m. In January of this year, the versatile attacker joined Barcelona for £142m ($170m).

"Philippe Coutinho is the biggest regret in more than 20 years at Inter," chief sport officer Piero Ausilio recently confessed.

In 1991, Lothar Matthaus was the recipient of the inaugural FIFA World Player of the Year award. Just over a year later, Inter decided to allow the German to return to Bayern Munich.

With the injury-prone Matthaus having suffered knee ligament damage in April 1992, the Nerazzurri had assumed that the 31-year-old was essentially finished at the highest level. 

They were wrong, though. Although Matthaus would never again be the fearsome box-to-box midfielder that inspired West Germany to World Cup glory at Italia '90, he was reborn as a sweeper after rejoining Bayern.

Indeed, he won four Bundesliga titles, and the UEFA Cup, during his second spell in Bavaria, and was even crowned German player of the Year, in 1999, at the grand old age of 38.

Andrea Pirlo was on the books of his Inter during one of the most turbulent periods of the club's history. 

Indeed, the Nerazzurri went through six coaches in just three years. "I'd wake up in the morning and I'd have forgotten who was training us," he later wrote in his autobiography.

Despite a successful loan spell at Brescia, during which he was converted from a trequartista into a regista, Inter allowed him to join city rivals AC Milan as part of a deal worth €18m that also saw Andres Guglielminpietro move in the opposite direction.

Pirlo blames then coach Marco Tardelli for his departure, arguing that if his predecessor Marcello Lippi had not been sacked at the start of the season, he could have "become a legend there".

Instead, he became a legend at AC Milan, winning two Scudetti and two Champions Leagues during his 10-year stint with San Siro's other side.

When Matthias Sammer arrived at Inter from Stuttgart in 1992, he was optimistic about his chances of settling quickly at San Siro.

"I'm sure that [Lothar] Matthaus will help me get to know this new Italian reality," the German said of his compatriot. 

However, Inter not only allowed Matthaus to return to Bayern Munich that summer, they also offloaded compatriots Andreas Brehme and Jurgen Klinsmann.

Sammer had no issues on the field, quickly proving himself one of the best foreigners in Serie A despite tactical issues with coach Osvaldo Bagnoli.

Off it, though, Sammer was struggling with the language, while his wife was desperate to go home.

Inter failed to help him adapt and allowed him to join Borussia Dortmund just one year into this three-year deal. 

It was a colossal mistake, as the sweeper went on to win the European Championship, the Champions League and the Ballon d'Or.

In March, 2002, Clarence Seedorf scored the most thunderous double in Derby d'Italia history. Just over two months later, Inter swapped him for AC Milan full-back Francesco Coco.

The latter was, at the time, a full-back of considerable potential but this was nonetheless an utterly bizarre deal. Seedorf had underperformed in his three years with Inter but he was a two-time Champions League winner, a truly gifted footballer who was outstanding on his day.

He proved this at Milan, with whom he became the first man to lift the Champions League with three different clubs. 

Unfortunately, Coco's time at Inter was less successful. A back injury played its part but his commitment to the game was also called into question.

Indeed, he participated in a reality TV show (Celebrity Island), tried his hand at acting and allegedly turned up for a trial at Manchester City smoking a cigarette, earning him the nickname 'Coco the Clown' in the English press.

Inter president Massimo Moratti was willing to do whatever it took to unite Christian Vieri with Ronaldo at San Siro in the summer of 1999 and that meant breaking the transfer fee world record by sanctioning a €49m deal for the Lazio striker. 

However, it also meant allowing tenacious Argentine midfielder Diego Simeone to move in the opposite direction. Vieri may have brought goals to Inter but he didn't deliver titles. 

Simeone, by contrast, helped Lazio win only their second ever Serie A title at the end of his first season in the Italian capital.

Even worse was to follow for Inter, though, as Simeone scored the go-ahead goal for Lazio in their infamous 4-2 win over the title-chasing Nerazzurri on the final day of the 2001-02 season.

He refused to celebrate out of respect for his former club but then, he didn't need to. By that stage, the point had already been made: Inter should never have let him go.