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Liverpool controversial free transfer to Real Madrid amid Trent Alexander-Arnold links

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The La Liga giants failed in a bid to sign the England international for a cut-price fee during the January transfer window.

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But while some Reds supporters will be disappointed if Alexander-Arnold chooses to depart this summer, this isn’t the first time the Anfield club have controversially lost one of their stars to the Spanish giants on a Bosman.

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A graduate of Liverpool’s academy system, McManaman swapped Anfield for the Santiago Bernabeu in the summer of 1999.



He would go on to win two Champions League and two La Liga titles during his time in the Spanish capital.



Reflecting on the move back in March 2021, McManaman revealed he might have remained at Anfield had the club’s chiefs tried harder to offer him the contract he felt his talents deserved.

The England international also revealed that he had a four-second meeting on his Liverpool contract negotiations, swiftly rejecting the Reds' poor offer.

“I was getting to the end of my Liverpool contract,” he recalled on the Robbie Fowler Podcast.

"I felt Liverpool were very slow in coming to me with a new deal.

“As it got on, two years, a year and a half, a year to go of the contract, I just felt that the opportunity now to play abroad – which I’d always wanted to do, I was always thinking about doing – was more prevalent than ever.

“I felt that the Liverpool team I was playing in, if you look back, and I’ve said this on numerous occasions, I hadn’t played in the Champions League at that time.

“My football was very good in 1996, 97, 98 and I felt I just wanted to be playing at a higher level than I was at Liverpool.

“I felt that Liverpool were on the cusp of a change, which was proven right when Gerard Houllier came in without anyone telling Roy Evans about it and I just felt it was the time to leave.”

The now TV pundit then continued: “It’s different now.

Some players had come in and earned two, three four times more than me.

“I didn’t have an agent at Liverpool so I was never chasing, I was always leaving it up to them and you always felt that they thought ‘He’s a local lad, he’ll be ok’ and it certainly wasn’t the case with me.

“When they came with their contract offer first, it was a case of trying to get everybody in the room.

I can easily come to Anfield, just let me know.

“I think I got told we’ll have a meeting in September and the meeting happened in April – and the meeting lasted four seconds.

“We’re going to offer you this, we’re going to offer you that, and I just said, 'No, thank you’ and then that was it.

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