In the last five years Luis Jiménez has played for Inter, Lazio, West Ham, Parma and Cesena. He has scored goals in Serie A, the Premier League and even one in the Champions League. He has commanded millions of Euros in loan fees and represented his country, Chile, in a pair of World Cup qualifiers. And yet, at the end of this season – one in which he is so far Cesena’s joint-top scorer – he’ll have a fight on his hands just to avoid winding up back at a third-tier club.

Almost a decade has passed since Jiménez, then a wide-eyed boy of 16, first arrived in Italy, accompanied by a friend of a friend who had agreed to bring him to the peninsula to help him get a trial. After impressing at the Viarreggio youth tournament he received offers from Parma and Ternana, but decided to accept the latter. Little could he have known that this was the footballing equivalent of settling in at the Hotel California. Ten years on he has checked out many times, but he is yet to truly leave.

The early years were happy enough. Jiménez was playing well – his goals tally reaching double figures in each of his first two full seasons as Ternana, then in Serie B, posted solid upper-midtable finishes. Then, in January 2006, the player finally made the step up to top-flight football, Fiorentina paying €2.5m to sign him on a co-ownership deal. He would be a regular fixture in Cesare Prandelli’s side for the remainder of the campaign. With Ternana getting relegated from Serie B, the assumption was that he would stay with the Viola.

That, though, was when things began to go awry. When the time came for the co-ownership to be resolved at the end of the season, Ternana outbid Fiorentina. Jiménez, horrified at the thought of dropping from top-flight to non-league football, made no secret of his displeasure at this development. The club, in turn, responded by freezing him out of training. Despite repeated protests to the Italian Football Federation, he was left to spend the first half of the 2006-07 kicking his heels on the sidelines.

Finally he was loaned to Lazio in January, but the option to buy at the end of the season was placed at a prohibitively high €11m. After two goals in 16 games, Lazio unsurprisingly declined to pay up. The pattern was set. Inter were next up, signing him first on loan in 2007, then on co-ownership a year later, but Ternana never relinquished their share. After two seasons with the Nerazzurri, Jiménez spent the 2009-10 season out on loan at West Ham, then Parma. And then Ternana bought back Inter’s share.

The fee was bewildering for a club of Ternana’s size. Still playing in the third tier, the Rossoverdi paid €3.2m to secure full ownership after a blind auction in which the Nerazzurri had offered little more than half of that figure. Jiménez, understandably, was distraught. The contract offer on the table at Inter had been a multi-year deal worth a reported total of €10m. At Ternana he would be paid €110,000 a season.

Only on the final day of the summer transfer window did Cesena finally agree to pay a hefty €1m up front for a season’s loan, with an option to make the deal permanent for €8m. Even if the club does achieve top-flight survival – a goal that looks distinctly achievable on current form, the Cavallucci Marini having moved out of the bottom three after a run of eight games with just one defeat – that fee may still prove prohibitive.

Jiménez is, in his own words, “a hostage”. “I feel blackmailed,” he told the magazine Sportweek, claiming that Ternana convinced him more than once to renew his contract by threatening to prevent him from going out on loan. “They promised, guaranteed, reassured me [that I would be sold], but at the point when words need to become deeds: nothing. They want a lot of money from my sale, but nobody seems prepared to take the matter by the throat.”

Most curious of all, it is no longer even clear who exactly is holding out for this theoretical fee. Ternana themselves were sold in the summer, with Angelo Deodati taking over from Edoardo Longarini, but immediately after taking over the new owner told reporters that Jiménez was still his predecessor’s concern. “Our takeover deal does not provide for Jiménez’s rights,” said Deodati at the time. The player himself lamented that: “I am not owned by Ternana, but by Longarini”.

That is not a situation Jiménez would seek. Relations between the pair broke down long ago, in the aftermath of the player’s initial recall from Fiorentina. “One time [Longarini] said to me: ‘Jiménez, how many years do you have left on your contract with us? And how much do you earn? Look, I’m rich. I can make you a bank transfer right now, I can give you everything you are due, and keep you here’,” claimed the player in his interview with Sportweek. “This is not freedom.”

There is, though, some light at the end of the tunnel at last. Jiménez’s existing deal at Ternana runs until 2013, but under article 17 of Fifa’s transfer rules, he will finally be able to buy himself out of that contract this summer. Even this, though, feels like a double-edged sword. “The awareness that this is the only way I can resolve the problem makes it feel like an obligation, something I am constrained to do,” says Jiménez. “And all the more so because by rule I could only go abroad, while I would rather stay in Italy.”

Having fathered triplets with his wife Maria in June, it is easy to see how the thought of uprooting the family and moving to a new country would be daunting. But if that is the price Jiménez has to pay to escape the Hotel Ternana for good, he will surely reason in the end that it is one worth playing.

Paolo Bandini covers Italian football for guardian.co.uk and Astro SuperSport, as well as The Score. You can follow him on Twitter @Paolo_Bandini.