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Heard the one about the Irishman who was released by Boro then signed by Juventus?

Juventus’ squad in 1999 was a who’s who of European footballing royalty.

Edwin van der Sar in goal, Gianluca Zambrotta and Ciro Ferrara in defence, Edgar Davids, Antonio Conte and Zinedine Zidane in midfield, Filippo Inzhagi and Alessandro Del Piero up front, all governed by Carlo Ancelotti.

Pretty tasty, right?

Juventus

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But one of the lesser spoken about members of the squad is the man at the centre of one of the most surprising transfers of all time.

Ronnie O’Brien. Does the name sound familiar? Don’t feel too bad if it’s not. Even the most ardent Juventus fan would be hard pressed to pick him out of a crowd.

In February 1999 O’Brien was released by a Middlesbrough side managed by Bryan Robson, on their way to a ninth place finish in the Premier League.

Paul-Gascoigne

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Deemed not good enough to to fit into a squad featuring the ageing talents of Paul Gascoigne, Andy Townsend and Gary Pallister, soon to be invigorated by the loan arrival of Juninho Paulista.

At 19 he was on the footballing scrapheap.

But he did have pedigree, as part of the Republic of Ireland side that won the European Under-16 Championships alongside Damien Duff and Robbie Keane.

Robbie-Keane

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However it’s not over until the Old Lady sings. And when the Old Lady came calling for O’Brien’s services, he didn’t need to think twice.

Juventus had only ever seen O’Brien play on video but, with a ringing endorsement from Paul Merson, took a very un-Italian gamble on his talents.

He signed on a five-year deal, joining some of the best footballers on the planet in training as he was too old to play for Juventus’ youth sides.

Antonio-Conte

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This is where the fairy tale finishes.

O’Brien wasn’t able to crack Juventus’ first-team, which is nothing to be ashamed about given the calibre of player he was trying to dislodge.

Loan spells at Swiss Super League side Lugano, Crotone and Lecco was followed by a stint with Dundee United at which point it was clear his time in Italy was coming to an end.

Ronnie-O

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But he didn’t stop touring the world.

The Irishman’s next stop was FC Dallas, where he stayed for the next five seasons, earning selection for the MLS All-Star team three times, before moving to Canada to play for Toronto FC.

At Toronto he was deemed good enough to earn a call up to Ireland’s squad, although he rejected it to work on his fitness, having just recovered from injury.

Ronnie-O

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The curtain came down on his career after a final season at San Jose Earthquake.

A career with more twists and turns than Liam Brady at his unstoppable best.

While he never made a name for himself at Juventus, he can always be safe in the knowledge that his name crops up at least once a week at pub quizzes up and down Italy.

Bellissimo.