Andrea Dossena's time at Liverpool was largely disappointing, but he did go down in Anfield folklore with the crowning goal in their 4-1 demolition of Manchester United in 2009.
That Old Trafford lob was the highlight of his Liverpool career, as the left back will be joined by the likes of Antonio Nunez, Andriy Voronin and Philip Degen as some of Rafael Benitez's worst signings.
After just 18 months on Merseyside, Dossena went back to Italy with Napoli, but returned to England in 2013 with Sunderland, but again didn't last long, having been released after only one year on Wearside.
Having gone all summer without a great deal of interest, it was difficult to see where Dossena's next move would come from. At 33, he was clearly past his best, and even when he was allegedly in his prime, he struggled at Liverpool.
However, he's once again been handed a route back into English football - it's just this time, it comes in the third tier of the pyramid.
Leyton Orient may have reached the League One play-off final last season, but it's recently gone horribly wrong at the Matchroom Stadium.
Italian Francesco Becchetti took over the club in the summer, and after manager Russell Slade moved on to Cardiff City, he has started an Italian revolution in London.
The new boss is former Perugia defender Mauro Milanese - who has no managerial experience - and his first signing was experienced target man Gianvito Plasmati, who has been without a club since the collapse of Italian club Siena.
Now, Dossena is the next Italian to make the move to Orient, joining on a deal until the end of the season as Milanese looks to drag the O's away from the League One relegation zone.
His experience at the highest level may come in handy, but it's evidently clear that Dossena is well past his best - so expecting a big impact would be foolish.