Jamie Redknapp criticised former team-mate Jamie Carragher for his persistent suggestions that Trent Alexander-Arnold should renew his Liverpool contract to avoid leaving on a free, accusing his Sky Sports colleague of being "very unfair".
The full-back's deal, alongside those of Mohamed Salah and Virgil van Dijk, is set to expire at the season's end.
Despite Salah's clear intentions to remain at Anfield, uncertainty clouds the futures of Alexander-Arnold and Van Dijk. Speculation has suggested Alexander-Arnold desires a move to Real Madrid to team up with Jude Bellingham.
On Sky Sports' Super Sunday, Carragher attempted yet again to convince Alexander-Arnold to commit to Liverpool, noting the deep connection as a local player who's been part of the club for two decades.
He said: "I just think as a local player. It is a long time living in that city. Trent has been at the club for 20 years, I don't think it would be nice for Liverpool supporters, whether you agree with them or not, to feel like: 'Hang on, we are winning everything, what more do you want?'"
Redknapp, however, blasted this approach on account of Liverpool's mishandling of the situation: "I think it is negligence from Liverpool, the fact they are in this position [with his contract expiring].
"If you are going to do that, you have got to respect that he has a decision to make. A young player who has given everything to the club, if he wanted to try a different culture [then why not].
"If I was in that dressing room, I would go: 'I would love you to sign, but good luck.' If there is a chance to got to Real Madrid, how do you turn that down? If I was advising Trent, a lot of it is to do with the free transfer."
Carragher then responded: "It is that feeling that you are leaving us for nothing, where is our money to replace you? I would say, sign a contract, have a decent buyout clause that's not ridiculous and if Real Madrid wanted to buy you in 12 months time..."
But Redknapp then interjected, arguing: "I think you are being really, really unfair. You can't turn round and tell him to sign a contract."
"If he gets injured after signing a contract, then what happens? He has got an opportunity for a five-year contract or whatever at Real Madrid and try something different.
"I have total respect for whatever it is he wants to do because he has given everything to Liverpool."
Carragher concluded the discussion by stating he was merely expressing the sentiments of Liverpool fans: "I am saying that Liverpool supporters... I am with them every day on the streets of Liverpool and I know how they feel.
"Doesn't matter if we agree with that. I think if you have been at a football club for 20 years, since the age of six, when you look back when you are 40 or 50, you still want to be one of those legends."