Jamie Carragher has revealed that he pleaded with Michael Owen not to leave Liverpool for Real Madrid in 2004, and tried to get him to come back to Anfield five years later.
Owen, 33, announced on Tuesday that he would retire from football at the end of the season.
The former England international signed for Stoke on a free transfer last summer after being released by Manchester United, but has been hampered by injury problems, failing to make a single Premier League start for the Potters.
Liverpool vice-captain Carragher, 35, who is also retiring at the end of the season, has hailed Owen as a "supreme goalscorer", recalling his exploits in the 2001 FA Cup final.
However, the defender believes that his former team-mate made a mistake in leaving Anfield for Spain.
"Michael and I were rooming in America during Liverpool's pre-season tour when he told me that Madrid had made him an offer and he was thinking seriously about it," he told the Daily Mail. "Liverpool had just signed Djibril Cisse, and Milan Baros had returned from Euro 2004 as the winner of the Golden Boot. Michael felt the time was right to pursue a fresh challenge.
"I told him he was making a mistake, that Madrid were a football club rife with politics and he wouldn't play. They had Raul and Ronaldo, who always played, and to be a success at Madrid, you had to be more than just a goalscorer, but Michael wouldn't be moved. He thought he was the best and would become a success in Spain.
"And in difficult circumstances, he did very well. Despite Real Madrid having three managers that season and him getting limited starting opportunities, he scored 16 times in 45 appearances. He may not have won any honours but his reputation was not harmed."
Carragher was disappointed that Owen did not return to Anfield when he came back to England in 2005, instead joining Newcastle before going to Old Trafford four years later. And the Liverpool man feels the United move was a mistake too.
"Liverpool supporters did not take too kindly to the way he left but I'm a firm believer that time is a healer and I'm sure they would have welcomed him back after his contract at Newcastle had expired," he said.
"I had heard he was thinking of joining Manchester United but he would have jumped at the opportunity to come back to Liverpool. He would have been happy to be a squad player and was excited at the opportunity to return home. The way he left Liverpool had saddened Michael and he wanted the opportunity to redeem himself.
"Joining United was a mistake. It ruined any chance of him repairing things with Liverpool fans and it's safe to say United supporters never really took to him despite his famous winner against Manchester City.
"Maybe he should have made this decision a couple of years ago or taken the chance to play in America or the Middle East. Something doesn't seem right about him potentially bringing the curtain down on his career sitting on the bench when Stoke play Southampton.
"But that won't diminish my memories or opinion of him. He was a supreme goalscorer, capable of glorious moments, and the goal he swept past David Seaman in the Millennium Stadium in that 2001 final provided my finest Liverpool moment until Istanbul. For good reason it will be remembered as the Owen Final."