Damien Comolli has claimed that Liverpool's American owners once described the signing of Jordan Henderson as a "massive mistake".
The Frenchman spent 18 months at Anfield as director of football strategy and director of football after being appointed by Fenway Sports Group in 2010.
During his time, he oversaw the signings of Henderson, Andy Carroll and Stewart Downing, but Comolli has claimed that the owners were not keen on one of their new midfielders.
Henderson was reportedly close to leaving Liverpool in a swap deal involving then-Fulham player Clint Dempsey, but a transfer never materialised and the midfielder has gone on to become vice-captain.
"When I left Liverpool, the owners told me Henderson was a massive mistake," the Liverpool Echo quotes Comolli as saying. "Now he's turned out to be the next Liverpool captain and he's a regular in every game.
"The issue I have got is when a group of owners approach somebody like me and say we want to invest for the long term, we want you to sign young players, we want you to put together a squad which has a future for the next three to five years, we want you to work with the academy and we start to do all this and after a few months or a few years they say, 'sorry, it's not working out'."
Henderson joined the club from Sunderland in 2011.