Liverpool ambassador Gary Gillespie believes the club should let Ryan Kent join Rangers.
The youngster is not needed at the Reds, given the quality of Jurgen Klopp's 23-man squad.
But the club also do not want to loan him, as they would prefer the money from a sale.
Gillespie believes it is the wrong move for the player.
He told the Daily Record: "The irony is that Liverpool let Harry Wilson go on loan to Bournemouth so that's a strange one. He's at a similar stage in his career, so I'm not quite sure what the difference is.
"Harry Wilson was pretty successful at Derby County last season and Ryan was a success at Rangers but I don't see the difference between the two lads.
"Ryan is a good player and would certainly enhance Rangers' starting XI but he's a Liverpool player and they call the tune.
"It's not as if he's a Lionel Messi or a huge name who can force the issue as we've seen so often with superstars who play up and get their agents to agitate for a move.
"But after what he experienced with Rangers last season he's at the age where he needs to be playing on a regular basis for a big club and not just for the Under-23s.
"Not many kids started at Academy level and reach the first team. Trent Alexander-Arnold has done it and Steven Gerrard did it before him.
"But you can stay too long at a club and I look at Alex Oxlade-Chamberlain and Theo Walcott who probably stayed too long at Arsenal.
"There comes a time where you need to make that move to regular first team football and sometimes you need to drop a level to come back up again."
