'I'm a Serie A legend and Liverpool is the only club I would have left Italy for'

All football clubs have ‘what might have been’ moments when it comes to transfers which didn’t happen. Antonio Di Natale recently revealed that he almost joined Liverpool in the Rafa Benitez era.

He would have been following in the footsteps of Andrea Dossena, who became a short-lived cult hero for the Reds. Nobody would claim his time at Anfield was a resounding success, but goals against Real Madrid and Manchester United in the space of four days was a surefire way to ensure he will be remembered forever.

Dossena joined from Udinese, the club at which Di Natale spent the final 12 years of his illustrious career. As he recently told Sportweek magazine in Italy, his career could have taken a path to the red half of Merseyside.

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"When Andrea Dossena signed in 2008, Liverpool spoke with me, but it all came to nothing,” Di Natale said (via Daily Star ). “Udinese taught me work ethic and respect. The only other team I would have loved to play for, for the atmosphere and the stadium, is Liverpool ."

Three weeks after Benitez signed Dossena, he bought French teenager David N’gog from Paris Saint-Germain. It’s reasonable to assume Di Natale was his preferred target at the time, so it’s fascinating to wonder how the title challenge of 2008/09 might have played out had the Italian joined instead.

First choice forward Fernando Torres was only fit to make 24 league appearances in that campaign. In Di Natale, Benitez would have been able to call upon a back-up approaching the peak of his career rather than a youngster still finding his way in the game.

The Italian would later prove to be more productive than even the Liverpool manager of the time could have hoped. In the summer of 2008, Di Natale was coming off the back of his best season in Serie A, a campaign in which he scored 17 league goals.

But he blasted that out of the water by scoring 29 times in 2009/10 despite being 31 years old when the season began. Di Natale then got 28 the year after, before netting 23 Serie A goals in both 2011/12 and 2012/13.

In an alternate universe, he might still have been at Liverpool by the time Jürgen Klopp joined, as he retired in 2015/16. But even if that stretches plausibility a touch, it’s realistic to picture Di Natale playing under Benitez and maybe – maybe – firing Liverpool to a league title at United’s expense. What might have been, eh?