​It was probably the most tormented and tempestuous summer that Florentine football has ever known. While the rest of the country was anxiously anticipating the start of Italia ’90, the streets of the Tuscan capital were simmering with anger and discontent. Most people remember the transfer which was at the centre of that outrage, not so many can recall the player who travelled in the opposite direction a few months later.

There has hardly been a more controversial signing in the story of Serie A than Roberto Baggio’s move from Fiorentina to Juventus. Losing the player who had become the heir to the affections they had afforded Giancarlo Antognoni was bad enough but to see him snapped up by the despised Gobbi – the Hunchbacks – truly gave them the hump. Any player taking over the legendary Viola number 10 shirt was walking into the eye of an emotional storm.

Step forward, Massimo Orlando.

The boy from San Donà di Piave was no shabby replacement, in truth. Having caught the eye with Reggina – coached by Nevio Scala – as well as Italy’s Under 21 side, the stylish midfielder was snapped up by Juventus in a deal worth about £2.7m – something like £6m nowadays. Not a bad price for a footballer who had only just turned 19.

But he wasn’t destined to last long with the Bianconeri. He did not make a single league appearance with La Vecchia Signora and the more methodical midfielder Eugenio Corini was preferred to him on a regular basis. “It’s obvious if I’m not playing I can’t show what I’m worth,” he said in one interview at the time. “I knew the move from Reggio to Juventus would not be easy but I didn’t imagine there would be so many problems.”

A chat with the club and his manager, Gigi Maifredi, and he was dispatched to Florence on loan in October 1990 to make his Serie A debut in a 1-0 defeat at the Stadio San Paolo against Napoli. For a support which was starving for a hero, he quickly went about feeding that hunger.

It didn’t take him long to endear himself to the Curva Fiesole, he scored a stonking goal on his home debut against Genoa and set off to celebrate in front of his new fans. The strike announced him as a major presence in a Fiorentina side which had just been sold to new ownership of father and son film producers Mario and Vittorio Cecchi Gori. Although the club would struggle all season long, Orlando probably enjoyed his best campaign in a purple – or any other – shirt.

He was no Roberto Baggio, that was pretty clear from the outset. He lacked the dribbling and easy eye for goal of the Divin Codino but he was an exquisite attacking midfielder on his day. He could dictate the play, set up goals for team-mates and often break into the box himself. All from beneath a foppish fringe which made it something of a miracle he could even see the ball, never mind conjure up anything magical with it at his feet.

The enfant prodige of Italian football had a tough task to raise Florentine spirits, though. They had lost out in the UEFA Cup final to Juventus the previous season as well as losing Baggio and were a side in a state of flux. It was a workmanlike outfit skippered by Brazilian Carlos Dunga and with the grafting Czechoslovakian Lubos Kubik as its second Straniero. The third was Romanian Marius Lacatus who was supposed to bring a dash of skill and goals to the team but singularly failed to deliver on that front.

It put an enormous pressure on the young Italian to deliver any excitement for the Viola faithful in a campaign where the club would huff and puff its way to avoiding relegation by just half a dozen points. Under Brazilian Coach Sebastiao Lazaroni they rarely put together any great run of form. It was only the odd splash of Orlando magic that helped their season to get off the ground.

It was just such a moment which would really win over his new supporters. An away trip to Turin to take on Juventus, and Baggio himself, was a chance to shine and he did not waste it. He scored the goal which gave the visitors a lead which would eventually be overhauled in circumstances which had captain Dunga raging.

“Everyone could see there was a Schillaci handball on their second goal,” he fumed. “Only the referee saw nothing. It is impossible for Fiorentina to win in Turin, I am above all sorry for our fans, but the most you can hope for is a draw.”

“It was an important game and I wanted to do well,” admitted Orlando after scoring against the club which still owned him. He was also given higher marks in the sports pages than the man he replaced in Florence. “Me better than Baggio? I can understand him, it was a difficult day.”

It was the start of a golden spell where he became an integral part of the Fiorentina team. His little feints, twist and turns and intuitive assists for his team-mates were often a match-winning contribution. He finished his first campaign with eight goals from just 25 Serie A appearances and ended up that season’s top scorer for the Viola alongside another man at the club on loan – Milan’s Diego Fuser.

His performances in a stuttering side were enough to convince the Tuscans to make his deal permanent and he became a key element of the side for the following two campaigns. The goals started to become more sporadic but the arrival of a certain Gabriel Batistuta at least took that pressure off Orlando. The trouble was that while the team looked better on paper, it struggled to deliver on the pitch and finished 12th in 1991/92 and then, incredibly for a side containing Batigol, Brian Laudrup, Stefan Effenberg and Francesco Baiano, got relegated the following year. It prompted a managerial change which – along with a string of injuries and operations – sent the attacking midfield man’s career into a downward spiral.

Claudio Ranieri helped to guide the team out of Serie B but he only used Orlando 19 times in the league and, the following year, he went on loan to Milan where he scarcely featured. He returned to Florence but the special feeling had gone and, perhaps more importantly, Portuguese maestro Rui Costa had arrived. Orlando felt forlorn about his time under Ranieri: “He would make me warm up for 80 minutes and then send someone else on.”

He had become a bit part player by the time he made his final appearance for Fiorentina, in Florence, in May 1997 against Reggiana. In total, he notched up 109 Serie A games for the club with 15 top flight goals to his name – the majority of them in that first season. He moved to Atalanta and, later, little Pistoiese, but he could never regain the fitness or form necessary to play with any regularity. He was just 30 when a career which had promised so much was over.

There were trophies but most of them gained in a peripheral role. He was in the Italy Under 21 squad which won the European Nations in 1992 but did not feature after the quarter-final stage. He did, at least, play a part in Fiorentina’s Coppa Italia victory of 1996, getting about three-quarters of an hour across the two legs against Atalanta. The rest of the honours that he is credited with in the record books – a European Supercup with Milan and Italian Supercups with the Rossoneri and Fiorentina – did not see him actually play the final matches. It was a lot less than his first forays into the game had promised.

Nowadays, he works as a TV pundit with the same distinctive floppy hair he had back in his playing days. He was put through the physical and emotional mill by football but he doesn’t seem to hold any grudges. He might not, ultimately, have proved to be anything like the player he replaced in Florence some 25 years ago but – for one glorious season at least – he helped to ease fans’ pain at the loss of a Viola idol.

Thanks to Giancarlo Rinaldi for this superb piece. Please follow him on Twitter @ginkers