Diego Milito was awarded the ninth annual Bidone d’Oro – the Golden Dustbin – on Monday, having been voted by listeners to Radio Rai 2 as Italian football’s worst performer of 2011. He joins a proud list of winners including Rivaldo, Christian Vieri, Adriano, Adriano and Adriano.

Was the Argentinian really this year’s most deserving candidate? Probably not, and certainly it seems odd that players such as Amauri – who despite his struggles at Juventus did superbly at Parma during his loan spell there in the first part of this year – and Diego Forlán – who has scarcely been fit since joining Inter from Atlético Madrid in the summer – should feature on the shortlist. Not that this is anything new. For evidence of this award going to the wrong man, you need look no further than its very first edition.

“This was an act of disrespect to a world champion,” spluttered the Brazil coach Carlos Alberto Parreira as word of Rivaldo’s 2003 Bidone d’Oro went global, but far more outrageous than the slight in itself was the fact of who he had beaten into second place. Saadi Gaddafi, son of the Libyan leader Muammar, had just completed his first six months with Serie A club Perugia – failing to get on the pitch once between his arrival in June and his suspension following a positive test for nandrolone in October.

Of all the many indulgences of Luciano Gaucci’s time as president of Perugia – from attempting to sign a female player to threatening to cancel a deal for South Korea’s Ahn Jung-Hwan after his goal knocked Italy out of the 2002 World Cup (in truth Gaucci did still try to complete the transfer, only for the player to understandably back out) – this was perhaps the most infamous. Gaddafi, in his own words a “deep-lying forward” had played for Al Ahly, Al Ittihad and the Libyan national team before his signing, but a deal based on merit this most certainly wasn’t.

An avid fan of, and shareholder in, Juventus, Gaddafi had long dreamed of playing in Italy. Thanks to his family connections he had been able to train with the Bianconeri for a period as well as others such as Lazio. He had employed Diego Maradona and the former Canadian sprinter Ben Johnson as personal trainers, too, and yet there had never before been any serious suggestion that any team was thinking of taking him on as a prospect. Especially not in the summer of 2003, a month after his 30th birthday.

Yet few football club owners have subscribed to the notion that any publicity is good publicity quite as wholeheartedly as Gaucci. No magnifying lens was required to read between the lines at the player was unveiled at the owner’s vast property in Torre Alfina. “We are all happy with an operation that will ensure we enter into the history of calcio,” tootled Gaucci, apparently oblivious to the notion that there might be better or worse reasons for doing so.

There was another layer to this story – raised by John Foot, author of the authoritative history of Italian football Calcio, in a recent blog for the New York Times – namely politics. Libyan oil was important to many Italian businesses, and Silvio Berlusconi had been quick to register his delight at the deal. He was soon leaning on Gaucci to ensure that the player found his way into the first XI.

Yet the problem remained that Gaddafi wasn’t very good. Asked about the player’s attributes shortly after the Perugia deal, Franco Scoglio, formerly the manager of Libya (a spell which had ended, incidentally, amid reports of Gaddafi being angered by an exclusion from the national team) did compliment his vision, but added: “his limits are evident in his lack of dynamism and his inability to adapt to a modern game in which everyone plays at high speeds.”

Perugia’s manager, Serse Cosmi, stalled as best he could, aided by first the nandrolone suspension – lasting just three months, after the authorities accepted Gaddafi’s claim that he had ingested the steroid unwittingly while receiving treatment for a back complaint – and then the player’s proclivity for picking up niggling injuries. But by May 2004 he was out of excuses. With a quarter of an hour remaining in a home game against Juventus, he sent Gaddafi on to replace Jay Bothroyd up front.

The timing was perfect – not only was the opponent Gaddafi’s favourite team, but Juventus were already a goal down, playing extraordinarily badly and had just had a man sent off. “Cosmi sent him onto the pitch one minute after the dismissal of Ferrara, effectively restoring numerical parity,” noted Gazzetta dello Sport’s match report the next day. “Saadi (that being the name printed on his shirt, Brazilian style) entered with his electric blue boots 15 minutes from the end, touching the ball twice in total. At 31 you can’t even say he’ll get better.”

Indeed, Gaddafi’s two touches had extended to one failed attempt to trap a pass and a cross met by nobody. Nevertheless his delight was apparent. Fabrizio Ravanelli, scorer of Perugia’s winner, noted in interviews that Gaddafi had promised to buy Smart cars for the entire team to celebrate.

But if observers imagined at that point that Gaddafi might feel his itch to have been scratched they were quite wrong. Despite that win over Juventus, Perugia were relegated to Serie B and the player went down with them. Yet even at this lower level and playing under a new manager, Stefano Colantuono, he failed to find room in the starting line-up – getting on the field for a total of 48 minutes across two Coppa Italia games but never appearing in the league.

Through it all, he retained a self-belief verging on the delusional. “Actually for me it would be easier to find a spot at Juventus then at Perugia,” he insisted when asked by Sportweek in April 2005 if he still dreamed of turning out for the Old Lady. “My technical attributes are best brought out by playing with fuoriclassi – I showed it in friendlies between Libya and All Star teams. But why are you asking about Juve, has there been talk of a possible transfer?”

The next summer he would engineer a move to Udinese, now coached by Cosmi, and there he would eventually get on the pitch for a further 11 minutes, coming on as a substitute in a 2-0 win over Cagliari, registering a more impressive 13 touches on this occasion according to the match report in La Repubblica. He even succeeded in testing the goalkeeper Antonio Chimenti with a left-footed volley. His final club would be Sampdoria, though here he would never get a game.

Today Gaddafi is wanted by Interpol, accused of misappropriating properties through force and armed intimidation when in charge of the Libyan Football Federation. It is a bizarre thought that just five years ago he was stepping onto the pitch at the Stadio Friuli to ironic applause – the absurdity of his career having allowed him to achieve almost a cult status. And just as bizarre to think that three years earlier, there was a footballing award which he deserved even more than Rivaldo.