Winger left hometown club for Real Madrid on a Bosman in 1999
When Steve McManaman left Liverpool for Real Madrid on a Bosman in 1999, it proved to be a good decision in regards to winning Europe's highest honours.
While the Reds would win a UEFA Cup crown as part of a treble alongside the League Cup and FA Cup that year, the Liverpudlian winger would become the first English player to win two Champions League titles as Real triumphed in 2000 and 2002.
Liverpool legend Phil Thompson was assistant manager to Gerard Houllier at Anfield at the time the transfer happened and he reminisced about the turn of events in an interview with Off The Ball's Nathan Murphy at the launch of Sky Sports coverage for the 2017-2018 season.
"I came in in 1998 when Steve McManaman was leaving Liverpool to go to Real Madrid," he told Nathan in an interview that we will play out in full this Saturday on Off The Ball.
"We didn't know that at the time. So I came in November '98 and Gerard Houllier said to me, 'Phil, can you being a local lad, have a word with McManaman. His contract is up at the end of the year and we're trying to get him to sign a new contract. He's not having anything of it. Can you have a word?'"
Keith Andrews and Phil Thompson at the launch of Sky Sports' 2017-18 Premier League coverage
Thompson sat down with McManaman in an effort to talk the player round and the winger suggested that his mind hadn't been fully made at that point, leaving the possibility that something could be agreed.
Despite that, Thompson had noted something: "I came out of that meeting and I went to see Gerard Houllier and I said, 'He's got no chance of signing for us'. I said, 'His mind's made up. He's going somewhere else' because in January you could talk to clubs."
Thompson estimated that McManaman would have been worth about £10 million in those days and due to it being a Bosman transfer, Liverpool didn't benefit financially from the player's departure to Real Madrid.
"We felt probably hard done by," Thompson added.
Keith Andrews and Phil Thompson were speaking at Sky Sports preview of the 2017/18 Premier League season. Sky Sports will kick off the new Premier League season on Friday 11 Aug with Arsenal v Leicester.
159 live Premier League games will air on Sky Sports Premier League (Channel 402) this season including 3pm Saturday kick-offs exclusive to Sky Ireland customers.