With Chris Waddle released two months shy of his 36th birthday, Wednesday found themselves in need of someone who could excite the Hillsborough crowd as the former England winger had done over the previous five years.
Step forward Benito Carbone, for whom the Owls paid Inter Milan a club-record fee of £3m according to the Jason Dickinson book Sheffield Wednesday Miscellany - despite the emergence of teenager Ritchie Humphreys.
Humphreys had scored four goals in five games for David Pleat's side at the start of the 1996-97 campaign, firing them to the top of the Premier League and drawing comparisons with Marco van Basten, from Johan Cruyff no less.
But those would be the only goals Humphreys ever scored for the Owls, and Carbone quickly took over as the apple of the Hillsborough crowd's eye. The Premier League was just starting to take advantage of its earlier re-brand from a financial perspective, with overseas talents popping up throughout the division.
And while Wednesday had employed foreign players before Carbone, the fact he was the club's first Italian - and had the ability to fit the stereotype of a footballer from that particular nation - really helped endear him to the Blue and White half of Sheffield.
Six goals arrived during his first season in Sheffield 6, with 19 more arriving over the next two-and-a-bit campaigns, and three of them (against Liverpool, Newcastle United and Blackburn Rovers) appeared on the Premier League's run-down of Wednesday's top 10 goals. It probably would have been more but for the interest of fairness.
However, when compatriot and dressing room ally Paolo Di Canio was sold to West Ham in early 1999, the writing was on the wall for Carbone, whose refusal to appear as a substitute against Southampton the following September led to a bust-up with manager Danny Wilson and culminated in his transfer to Aston Villa for a mere £250,000.
He would later admit to the Daily Mail that one of his biggest regrets was failing to integrate with his English teammates - who liked to drink while he was teetotal.
Sheffield Wednesday career: 1996-99
Other clubs: Torino, Reggiana, Casertana, Ascoli, Napoli, Inter Milan, Aston Villa, Bradford City, Derby County, Middlesbrough, Como, Parma, Cantanzaro, Vicenza, Sydney FC, Pavia.