Five-year Juventus deal must've shocked Middlesbrough but they never felt Serie A regret | OneFootball

Ronnie O'Brien didn't make one appearance for Boro in two years and was released, so when Juventus signed him, it sent shockwaves across Teesside...

Middlesbrough signed promising young Republic of Ireland youth international attacking midfielder Ronnie O'Brien in 1997, and little did they know that just two years later, he and Boro would be involved in one of football's most bizarre transfers alongside Serie A giants Juventus.

At just 18, Boro handed the teenager his first steps in professional football by bringing the talented youngster across the Irish Sea as Bryan Robson looked to continue building towards a return to the Premier League on Teesside.

Despite not much being known about him, O'Brien was evidently a young player with a fair amount of talent and fellow midfielder in Robson clearly saw enough in him to warrant signing him.

However, after failing to make a single first-team appearance for Middlesbrough, O'Brien was released in the summer of 1999. As such, Boro supporters would've been forgiven for expecting to see him drop down the leagues to find his next club.

So when it was announced that he'd signed a five-year contract with one of world football's biggest clubs, Juventus, the news sent shockwaves across Teesside.

O'Brien's Juventus move came as a complete shock, but Robson wasn't convinced of success

O'Brien's agent was Steve Kutner, who also happened to represent then Middlesbrough star Paul Merson, and it was he that brokered the deal for him to join Juventus.

It's understood that to help drum up interest in his client, Kutner packaged together some of O'Brien's highlights onto a videotape which was then sent to clubs across Europe, one of which was Juventus.

Having watched the tape, the Old Lady - who at the time were managed by Carlo Ancelotti - were sold and thus inked the now 20-year-old Irishman to a five-year deal in Turin.

Due to the stature of a club such as Juventus snapping up O'Brien, panic ensued among the Middlesbrough support that he would be one that got away from them, but Robson wasn't convinced.

“Ronnie O’Brien is not good enough,” proclaimed the Boro boss at the time. “People jump to the ceiling because he has gone to Juventus, but he hasn’t done anything yet. Good luck to him. I hope he does really well and proves me wrong.”

O'Brien then hit back at Robson, as it now developed into a war of words between the two individuals. “Things were going nowhere at Boro,” O'Brien said.“I didn’t think I was getting a chance.

“I thought I was playing well in the reserves, I scored a couple of goals, but then I didn’t even make the squad sometimes.

“I would have left anyway, I wouldn’t have signed a new contract. I didn’t feel there was any room at the club for me and I didn’t want to stay. Bryan Robson doesn’t like young players. He said that to us. He prefers experience.”

Robson put an end to the verbal spat by saying: “If kids are good enough I like them. If not I have no time for them. People have this thing about kids coming through, but they have to be good enough. I want kids who can get into the team, stay there and become seasoned professionals.

“Ask Robbie Stockdale whether I like younger players. Ask Ryan Giggs and the kids at Manchester United I saw grow up. I’m happy with my staff. Nobody we have rejected has done really well.”

So, would O'Brien prove Robson wrong, or would the legendary footballing figure be proven right?

O'Brien's time in Italy was a disaster, before salvaging what remained of his career in the MLS

His move to Juventus shot O'Brien to stardom, as he became just the third-ever Irishman to sign for the Italian giants. Rather hilariously, O'Brien almost won Time magazine's Person of the Century award as well, as people began to submit his name for the award via an online voting poll, to which he was leading at one point due to the sheer number of people joining in.

Time eventually changed the rules and removed O'Brien from consideration, but that just highlighted how quickly he'd gone from being a little-known Middlesbrough castaway to a household name at the time.

Ancelotti's side included the likes of Zinedine Zidane, Alessandro Del Piero, Edgar Davids, Edwin van der Sar and Filippo Inzaghi, and now a 20-year-old all the way from Bray, County Wicklow. It was truly a remarkable story.

Unfortunately for O'Brien, it didn't have a storybook ending. The majority of his three-year spell with Juventus was spent out on loan to the likes of Lugano, Crotone, Lecco and even Dundee United.

He did however go one better than his time with Middlesbrough when it came to appearances, with his only competitive action from his time in Turin coming in the form of a 13-minute cameo from the bench in an Intertoto Cup semi-final second leg against Russian side FC Rostselmash - know known as FC Rostov.

The summer of 2002 saw Juventus release O'Brien from his contract. Desperate to start playing regular football once again, he headed on his next great adventure, as he was signed by MLS side Dallas Burn - now known as FC Dallas.

He enjoyed a fruitful time with FC Dallas, playing over 100 times for the club, scoring 12 times and providing 25 assists across five seasons with the club, before spending his final two seasons of his career with Toronto FC and San Jose Earthquakes.

Robson was proven right with O'Brien and his move to Juventus, but the Irishman remains a cult figure to this day because of that move, in what is without doubt one of the strangest transfers in football history.