Jamie Carragher has compared Dimitri Payet asking to leave West Ham to Fernando Torres's Liverpool exit in 2011.
The France international has refused to play for Slaven Bilic's team after requesting a transfer, with former club Marseille failing with a £20 million bid last week.
Torres left Anfield on January deadline day six years ago, joining Chelsea for what remains a record fee between two British clubs of £50m, but failed to live up to his record at Liverpool with just 20 goals in 110 league appearances.
Carragher has questioned players' motivations to leave during a season and feels a January departure can severely affect reputation in the long term.
"I have always thought it hugely important how you leave a club," Carragher wrote in the Daily Mail . "Your reputation as a player lasts longer than your career and the way you handle yourself determines how you are remembered and regarded by supporters.
"There are ways and means of conducting yourself and I don't understand the logic in asking to leave a club in the middle of the season.
"I saw Fernando Torres do it at Liverpool, but I've never been in that position and honestly don't understand what players hope to gain.
"Why couldn't Payet have just given West Ham the remainder of the campaign? There are only 18 games left, so why can't he just put his head down, think about getting West Ham away from relegation trouble and then look for an amicable move in the summer?
"He was outstanding last year and even this season he has produced some standout moments. He could have preserved his legacy and ended up being revered like Paolo Di Canio. Instead, his stance has turned the whole thing sour."