Mark Viduka revealed Leeds United blocked him from joining Milan in a £38million transfer in 2001, while the Australian great also held talks with Manchester United.
Regarded as one of Australia's all-time greats, Viduka was a dominant force during his time with Dinamo Zagreb, Celtic, Leeds, Middlesbrough and Newcastle United.
Viduka spent four years with Leeds and helped the Premier League club reach the 2001 Champions League semi-finals, prompting interest from across Europe.
Serie A powerhouse Milan wanted Viduka but Leeds – eventually crippled by financial issues – prevented the former Socceroos captain from moving to San Siro.
"I had the chance to join AC Milan at the end of the 2001 season, after we made the Champions League semi-final," the 44-year-old told ESPN.
"[Leeds] were negotiating with Milan and wanted £38m. I was friends with [Milan star] Zvonimir Boban at the time, and we were negotiating terms through him. In the end, [Milan] offer the £38m, and Leeds didn't want to sell. And that was that.
"I was a huge AC Milan fan. As a kid, I grew up watching [Marco] van Basten, [Frank] Rijkaard and [Ruud] Gullit ... They were my favourite team. It just wasn't to be."
United – managed by Alex Ferguson at the time – were also admirers and tried to lure Viduka to Old Trafford, however, the 43-time Australia international opted to stay at Leeds.
Detailing a meeting with music icon Elton John, Viduka said: "I was in Manchester, and my agent at the time also had a lot to do with Elton John.
"He said stay for the night and come to the show. He had backstage passes, and I'd get the chance to meet the man for myself. It was an offer I couldn't refuse.
"So I'm there with Jacob Burns, my Leeds team-mate and fellow Aussie, as we got ushered into his dressing room. As we enter, Elton swings around on a swivel chair and says, 'Mark Viduka, you're from Melbourne. I love that place!'
"I was nervous, so I babbled on about my meeting with the Red Devils that day and a possible move. Instead of going to our seats to watch the concert, Elton gets us to watch it at the side of the stage. About three songs in, he says, 'I want to dedicate this next one to my good friend Mark, who is in Manchester today to make a big decision.'
"I'm thinking: 'S***, please don't say anymore!' Thank God he didn't. I didn't sign for Man United. I think I loved living in Leeds too much at the time."