As the car pulled out of Milanello on that mild morning, the man in the back sank down into the groove of the seat and pondered for a moment whether he’d made the right decision. What he was about to do was a big gamble, but the move was all but agreed by now, and as the early afternoon sun tried to poke through the trees that aligned either side of the path he swallowed hard and said a little prayer under his breath.

During the mid ‘90s, Serie A was the league to be seen in. It was able to house the type of players that the Premier League and the Bundesliga could only dream of attracting at the time; Marco Van Basten, Ruud Gullit and Gabriel Battistuta were all illuminating the mind and feeding the eyes of football fans the world over, but one of the most iconic stars of this generation was home grown; Roberto Baggio.

Baggio had been doing the rounds of some of the division’s most prestigious institutions, like Fiorentina, Milan and Juventus since breaking onto the scene with lowly Vicenza back in 1982. However, one of the most fascinating periods of his career came when he made the shock decision to join mid-table sluggers Bologna in 1997.

Serie A was a tough place to compete and will always have a special place in the hearts of men around a certain age, but without dipping into the rhetoric of Woody Allen’s Midnight in Paris too much, hindsight has now afforded us the realisation that the final decade of the 20th century was a golden age for football in many ways, especially in Italy.

Off the back of a successful World Cup, the money was flying, advertising had yet to make everyone completely cynical, the true extent of the league’s corruption had not been exposed, and in the UK at least, James Richardson presented it to all in a neat 60 minute package over oceans of steaming hot cappuccinos and mountains of gelato in a way Sky Sports or Match of the Day could never hope to live up to.

During this time Bologna were unfancied to do much in Serie A. They’d punched above their weight the season before and were largely tipped to amble along in the lower reaches of the division, or even slip back down to Serie B where many believed they belonged. The club’s fans were slightly more hopeful of being able to maintain a similar level of consistency, but those same fears were in the back of their collective conscience all the same.

It was also the year, though, that Baggio had seen his time with Milan come to a premature end as he found himself out of favour under coach Arrigo Sacchi, the very man he’d dragged along with him to the final of the 1994 World Cup in the USA. The aftermath of a series of disagreements had bled through from Fabio Capello’s time in charge, and the two had been known to argue during their time Stateside. As their Scudetto challenge unravelled, Sacchi limited Baggio’s playing time drastically. Over the summer, knowing that he had concerns over his place in Cesare Maldini’s squad for the World Cup in France the following year, Baggio decided something needed to be done.

Sensing his disgruntlement, Bologna coach Renzo Ulivieri went to the club’s owner armed with just hope, and asked him on his thoughts about making a move for Baggio. To his surprise, he had the club’s backing. Ulivieri contacted Milan, who in turn gave him permission to speak to the player, and just 24 hours later Baggio would stood next to a bewildered Ulivieri holding a Rossoblu shirt in front of the equally baffled media.

Baggio was a Bologna player just 24 hours after the club had made their initial approach. However, the move was met with wide derision. Many believed that at 30-years-old, this would represent the beginning of the end for his career and some even taunted him as a future Serie B player. He responded by cutting off his iconic ponytail as a symbol of his rebirth. He had high hopes that the gamble would pay off.

But the media’s taunts appeared to be vindicated when Bologna got off to a sluggish start. An opening day 4-2 defeat to Atalanta, in which Baggio scored from the spot, was followed by another 4-2 slump to Inter. Baggio got both Bologna goals, but they failed to score for the next four games, notching up three goalless draws and a 2-0 defeat to Parma. A 5-1 rout of Napoli proved to be a false dawn, as the side collected only two points from their next four games. Rumours of disquiet in the camp were doing the rounds too. Despite chalking up a hat trick in the Napoli thumping and two more in the subsequent games, the relationship between Baggio and Ulivieri was strained. The coach had left him out of the side for the visit of former club Juventus at the last minute following a disagreement over tactics. However, when quizzed on why his star man wasn’t in the side Ulivieri played down talk of a rift, describing Baggio as “a nice guy” and “a talented player”.

Results started to pick up, and Bologna were now finding the net on a regular basis. Baggio continued to form a good understanding with Kennet Andersen too, and helped the big Swede to a hat trick of his own in the win over Sampdoria, which was then followed up by victories over Vicenza and Udinese.

Baggio had an eye on his former club, eager to show what they’d been missing out on. Sacchi had now been replaced by the authoritarian Fabio Capello, but that didn’t seem to diminish the significance of the occasion. Baggio opened the scoring early on, latching onto a high through ball to pirouette and poke the ball past the on rushing Sebastiano Rossi. In an explosion of relief, Baggio ran to the side of the pitch and prayed whilst his teammates ran over to congratulate him, and he capped off another fine display by dispatching a late penalty after being brought down by Paolo Maldini.

With the season coming to a close, Bologna won four of their last five games. The only defeat coming away to Juventus, a game that Baggio later admitted he’d been dreading after missing out on the reverse fixture earlier in the season. But he got himself on the scoresheet once again, and this time ran along the touchline at the Stadio Delle Alpi with his hand cupped to his ear, as the now silent home crowd kept their insults to themselves.

Baggio finished the season 1997/98 season with 22 goals and six assists. Bologna had once again performed above their station, finishing in eighth place and qualifying for the following season’s Intertoto cup. But before that there was the small matter of the World Cup in France. Baggio had scored a brace in six games that season, and coach Maldini had no choice but to call him up. And even though he would be going up against Alessandro Del Piero, who’d astonishingly bagged 32 goals in 47 games across all competitions himself, his inclusion had been a popular decision.

Italy would begin their campaign against Chile. Led by Marcelo Salas and Ivan Zamorano, the South American’s were seen as dark horses of a talented group that also contained Cameroon and Austria. Things got off to a great start for Italy too, just ten minutes in Paolo Maldini intercepted the ball by his own area, looked up, and sent a wonderfully placed pass to the feet of Baggio, who had somehow slithered between two Chilean defenders to send a perfectly weighted ball into the path of Christian Vieri. 1-0. But Chile soon fought back, two goals either side of the break from Salas had the Italians on the back foot. But then, with just five minutes remaining, Baggio received the ball out on the right, as he darted into the area he flicked the ball up on the hand of Ronald Fuentes and won a penalty. A nation held its breath. As soon as the whistle blew, Baggio bent down, and with his hands on his knees began to compose a mantra. “Just hit it hard, hit it hard,” he later told reporters, and after a brief deliberation with his colleagues, he had the ball in his hands as he walked over to the spot. Looking just as cool and calm as he had done four years ago, he took another long run and fired past the outstretched hand of Nelson Tapia, exorcising the demons of that day in Pasadena, and in doing so became the first Italian player to score in three consecutive World Cups.

“It affected me for years. It was the worst moment of my career. I still dream about it. If I could erase a moment, it would be that one,” he’d later say recalling THAT moment in the USA.

As the group wore on Baggio continued to battle with Del Piero for a starting spot. He started against Cameroon, but came off after an hour, and then found himself on the bench in the final game against Austria. The Juve man ran the show that day, and laid on a cross for Christian Vieri to put Italy into the lead, but in a role reversal from the Cameroon game found himself sacrificed in place of the old master. Baggio would score again, thanks to some neat link up play with Filippo Inzaghi, who rolled the ball across the box to find his man waiting, unmarked, and with the net gaping at his mercy.

Having missed the last 16 game with Norway, he returned from the bench when his side met France in the quarter finals. Cesare Maldini had started with Del Piero again, and faced heavy criticism from back home as the 24-year-old was still recovering from injury. Del Piero had been largely ineffectual, and Baggio had the best chance to seal victory by a golden goal when his close range volley sailed past the face of the goal.

The game would be decided on penalties. Baggio, first up, dispatched his easily. He’d already put one away this tournament and there was no way he was going to mess it up this time. He slotted the ball past Barthez in the French goal and strolled back to the centre circle with his finger pressed to his lips. However, Italian hearts were to be broken again, this time by Luigi Di Biaggio, who sent Italy’s final kick crashing against the bar. The World Cup dream was over once again.

Upon his return, the jibes of four years previous has long been forgotten, Baggio had proven his detractors wrong and was once again a figurehead in Italian football, and sealed his good year by signing for Inter for a fee of just £2.2 million. It had taken him four years, but he was now a heroic icon once again, the wrong side of 30 perhaps, but in performing so well for a ‘lesser club’ he proved he was still worthy of mixing it up with the big boys.