At long last, Alberto Aquilani felt like things were falling into place. “I am very happy to be here,” said the midfielder upon completion of his move from Liverpool to Milan last August. “This is a turning point for my career.”

Yes, this was another loan deal, his second in as many years, but this time things felt different. The 2010-11 season spent with Juventus had been a wonderful experience, but even during his best spell for the club Aquilani was never confident Turin could become a long-term home. Although Juventus had the option to make the deal permanent at the end of the season for €16m, Aquilani always doubted the Bianconeri had the resources to stretch so far.

He would be proved correct, as Juve were unwilling to even meet a reduced asking price of €10m once they had procured Andrea Pirlo from Milan on a free transfer. Aquilani was obliged to return to a Liverpool side where, despite public words of encouragement from Kenny Dalglish, it seemed that he was not truly wanted. Fiorentina offered to take the player out on a season-long loan of their own, but Aquilani declined on the grounds that he craved something more permanent.

There were raised eyebrows in Florence when Aquilani agreed to join Milan on ostensibly similar terms. The Italian champions represented a more attractive option than a Viola team experiencing a period of transition, but the real devil was in the details. “Here the option is set at €6m and becomes obligatory if I play 25 games,” explained Aquilani, noting that Fiorentina’s proposed deal only included the option to buy at a twice-as-high €12m. “I felt like this was more of a guarantee.”

To Aquilani’s mind, this was a deal that put the power back in his hands. If he performed well enough, the manager Massimiliano Allegri would have to select him. And if Aquilani played, then Milan would have to buy. As excited as he was to join a club which he described as the pinnacle of Italian football, Aquilani’s greatest desire was simply to find somewhere, anywhere, to call home.

If he rejected the suggestion, put to him by Gazzetta dello Sport a few months into the season, that Juventus had represented some sort of career purgatory, describing it as “a fundamental step in my career”, it certainly felt as though he had spent the last two years locked in limbo. Born and raised in Rome, Aquilani had only ever dreamt of playing for Roma. Had it been up to him he would never have left, but with debts mounting in the summer of 2009 the club viewed his sale as its best hope of staying afloat.

“Nobody can understand what it means for a Roman, Roma-supporting player to leave Roma,” he told Gazzetta in the same interview. “I grew up convinced that I would stay with Roma for ever, like [Francesco] Totti and [Daniele] De Rossi, and yet at a certain point the club decided to put me on the market. It was hard to accept.”

Even harder to comprehend was his new manager’s reluctance to use a player in whom the club had invested so heavily. Although he had arrived carrying an ankle injury, Aquilani made his first appearance for Liverpool in a League Cup game against Arsenal before the end of October. Despite this, he wouldn’t get his first start until 26 December. Although injuries had continued to hamper his progress, it was certainly true that he had been available for a lot more than the 13 starts he eventually managed.

But if Rafael Benítez was chastised for using him so sparingly then he cannot have been the only one to harbour doubts. Aquilani followed up by playing 33 games for Juventus last season, performing well enough to establish himself as a regular member of Cesare Prandelli’s Italy side, even scoring the winning goal in a friendly against Spain over the summer. A 27-year-old with such credentials ought to have been one of the most sought-after figures in the summer transfer window, yet in reality there was no line of potential suitors knocking down Liverpool’s door.

Indeed, when Aquilani eventually arrived in Milan it was to an air of disappointment. The club’s vice-president, Adriano Galliani, had sparked rumours of another Zlatan Ibrahimovic-esque signing by referring to an unidentified “Mr X” at the top of his transfer shortlist, but the suggestion that Aquilani could be the man in question was met with derision. His mode of transport said it all: Ibrahimovic had flown into Milan the previous summer by private jet; Aquilani travelled with budget specialists Ryanair.

Despite such scepticism Aquilani quickly became a central figure, just as he had at Juventus a year before. Milan fans hoping that the midfielder might treat them to a repeat of his most famous trick—the outrageous rabona which helped set up Roma’s winning goal at San Siro back in 2008—would be disappointed (his one attempted reprise, in a Champions League group stage game against Viktoria Plzen, was rather less successful) but what they would get was a much-needed creative presence at the heart of Allegri’s 4-3-1-2.

Suggestions that Aquilani could be Pirlo’s successor at Milan had always been wide of the mark (the players’ respective styles are so different as to be scarcely comparable) but Aquilani’s vision, energy and versatility served the team well. He saved one of his best performances for his former team-mates, providing Ibrahimovic with two perfect assists in a 3-2 win at Roma.

By the end of October an eventual permanent transfer to Milan looked a formality. Already he had played in 11 games for the Rossoneri, (even if they would only technically count as nine towards the obligation to buy, with substitute’s appearances being considered as half-games) providing six assists and one goal. He added a further nine appearances—all but one of them starts—before the winter break.

Inevitably, a set-back was just around the corner. A fresh ankle injury suffered in early January would keep Aquilani out for the next two months. He returned in early March to find himself suddenly nudged out of the first XI, restricted to late appearances from the bench. From a contract standpoint, they did not add up fast enough. With five games left to play in Serie A, Aquilani remains three short of the 25 required to trigger an automatic purchase.

It is possible that Milan may yet make a move for him anyway, of course, that Galliani may simply seek a further price reduction in typically opportunistic fashion (and the €6m clause cited by Aquilani is believed to be nearer €8m when certain bonuses are factored in). Barring a speedy resolution, however, there is a significant prospect that the player could travel to Euro 2012 with his career, and his life, once more in limbo.