The former Rangers and Italy striker built his reputation as one of Europe's most lethal finishers during the 1990s, scoring goals wherever he played and becoming an instant icon at Ibrox.
Today, however, Negri looks at Italian football with mixed emotions.
While Serie A remains highly competitive and clubs such as Inter, Napoli, Roma and Milan continue to challenge domestically and in Europe, he believes one issue continues to haunt the Italian game: the lack of elite Italian forwards.
Speaking to Football Presse, Negri reflected on the state of modern Serie A, the growing influence of Scottish players in Italy and the challenges facing the Azzurri.
"Italian football is no longer the best in the world," Negri admitted.
"The Premier League and Spain are ahead and much of that comes down to television revenues.
"Once every great player wanted to come to Italy because there were huge salaries and it was the league that helped players grow and showcase themselves."
Yet Negri still sees plenty of quality in the modern game.
Inter's Scudetto triumph last season underlined the strength of the league, while Napoli remain among the contenders after Antonio Conte rebuilt the club into a title challenger again.
"The championship is very competitive," said Negri.
"There are many strong teams. Inter, Napoli, Roma, Milan and Juventus all have the quality to compete."
One development that has particularly caught his eye is the success of Scottish players in Serie A.
"It seems like a surprise, but this proves Scottish players can make the difference in Italy, especially in certain positions," he said.
"The Scottish midfielder is dynamic, aggressive and has great attitude."
Negri highlighted Bologna captain Lewis Ferguson and Napoli midfielder Scott McTominay among those who have adapted brilliantly to Italian football.
"McTominay is a special player. He is the modern midfielder because he can defend, attack and score goals."
He also praised Ferguson's resilience after injury interrupted what had looked like a rapid rise towards one of Italy's elite clubs.
"He deserved the interest from clubs like Napoli and Juventus because he was one of the strongest midfielders in the league."
Yet for all the positives, Negri keeps returning to one subject: goalscorers.
As a former striker, he understands the unique pressures of the position.
That is why he was particularly interested by the returns of Ciro Immobile and Andrea Belotti to Serie A.
Immobile's homecoming to Bologna offered one of the stories of the season before injury disrupted his progress and he left for Paris FC.
"Immobile was playing in a very aggressive team that creates a lot of chances," Negri said.
"He should now have many opportunities to score goals and return to being the player he was before.
"As a former striker, I know confidence is the most important thing for a forward. Scoring goals is the best medicine."
Negri was equally sympathetic when discussing Belotti, whose comeback at Cagliari was halted by a serious injury.
"Belotti was very unfortunate," he said.
"It looked like a rebirth for him and then he suffered another major setback.
"I can only wish him the best and hope he comes back stronger."
Those individual stories feed into a wider concern for Negri.
Italy, he argues, is simply not producing enough top-class attackers.
"When I was playing there were Vieri, Totti, Vialli, Mancini, Baggio, Del Piero and Montella," he said.
"There were so many world-class forwards.
"Now it is difficult even to find four or five top strikers."
Negri believes the problem starts long before players reach Serie A.
"It comes from the academies and the methodology being used.
"We need to look carefully at player development, the structures and how young players are being taught.
"Something has to change."
For a man who built his career putting the ball in the net, the challenge facing Italian football is obvious.
Serie A remains competitive. Its clubs remain respected. Its tactical quality remains among the best in Europe.
But until Italy consistently produces another generation of elite forwards, Negri believes one of the game's traditional superpowers will continue searching for the next great goalscorer.