Benito Carbone's career can be divided into two parts – the fearless Premier League trailblazer and the reflective coach who is now shaping Italy's next generation.
But one moment from his playing career still haunts him: the day he turned down a four-year contract at Aston Villa. Speaking to Gazzetta dello Sport, he explained why.
Aston Villa's decision that changed everything
At the time, Carbone was thriving at Aston Villa and enjoying the best football of his career.
With three goals in the FA Cup, he was joint top scorer with Alan Shearer and was part of the team that reached its first final in 26 years.
Then came Aston Villa's offer: four years of security, trust and stability. This is a deal that most players never hesitate to accept. Instead, he decided to walk away.
"At Aston Villa, I lost the 2000 FA Cup Final against Chelsea, the club's first in 26 years," He said.
“In that edition, I scored three goals against Leeds, and finished the tournament as top scorer along with the great Alan Shearer.
"It was a mistake not to renew with them: they offered me four years, but I wanted to go to Trapattoni and Batistuta's Fiorentina at all costs. In the end, I found myself in Bradford where I... did my military service."
Another regret: leaving Inter too soon
Transfer mistakes are something Benito Carbone now looks back on with interest. As Inter Milan's primavera coach, it is his job to shape the next generation of Italian football.
And that includes giving his advice to young players, especially when it comes to deciding their future. Carbone's message seems clear; Patience first.
His Aston Villa regrets come from his impatience to join Fiorentina, which never happened. Instead he would make his debut for Bradford in a pre-season game against the Italian side, one of life's small, unmistakable ironies.
But he also regrets jumping ship to Inter Milan. Had he not done so, he could have played among some great players.
"Although, yes, I have one regret: I left Inter too early," He added.
"With Hodgson, I played out of position, but if I had waited six months, Gigi Simoni would have arrived, and then Ronaldo. Everything would have changed. Sometimes in life you need patience, but I didn't know that then."
England, cult status and no regrets
Despite those regrets, Carbone has no regrets about England. He still enjoys cult hero status at Sheffield Wednesday, Aston Villa and Bradford. He later waived £3.2 million in unpaid wages to save the club from liquidation.
Loan spells at Derby County and Middlesbrough also followed before he eventually returned to Italy.
There was also a shared experience with Paolo Di Canio at Sheffield Wednesday, of which Carbone also speaks fondly. In fact, overall, England was a choice he does not regret.
"Let's just say it wasn't talked about much...at that time, there wasn't social media and the attention we get today," He concluded.
"Now, if an Italian scores in the Premier League, everyone knows about it. But England is an amazing experience. I even managed to learn English through gestures. After the initial darkness, by listening to TV and talking to my teammates, I unlocked myself in six months."
The focus now is on the Italian's future, and perhaps making sure he doesn't have regrets like the former striker. Today, Benito Carbone's story stands as a warning and a lesson for the next generation: sometimes the smartest move is to stay put.
