The former Republic of Ireland midfielder is now retired but once upon a time he was one of the most feared wingers in the British game, and helped form an exciting front three at Stamford Bridge with Arjen Robben and Didier Drogba.
But a lack of guaranteed game time forced Duff to move on after three years with Chelsea, and he eventually opted for Newcastle – even though he could have signed for Rafa Benitez’s Liverpool.
In an interview with FourFourTwo, the 37-year-old explained: “I came close [to joining Liverpool] two or three times. The first was a year or two before I signed for Chelsea [in 2003].
“I would have gone there, but Blackburn wanted a big fee so not too many clubs could afford to buy me back then!”
And on moving to Anfield when leaving Chelsea, Duff added: “I had friends at Newcastle – Scott Parker, Shay Given – and I wanted to give that a real go, but I had a disaster. I gave them everything but sometimes moves don’t work out.”
Duff might have won two Premier League titles whilst at Chelsea but it was still a wrench to leave the club and he admits to breaking down when his departure had been confirmed.
He revealed: “I cried on the day that I left [Chelsea] – looking back, that probably should have told me I was making the wrong call, as I never cried when I left Blackburn, Newcastle or Fulham, or even when I retired. But it was my own decision.”
It’s easy to forget just how good a player was back in his prime – could signing him have changed Liverpool’s fortunes back then? Could he have helped the Reds claim a Premier League title?