Jamie Carragher dropped former boss Rafa Benitez in it at the weekend, telling The Mail that the Spaniard snubbed the chance to sign Gareth Bale for Liverpool.
Carragher explained that Benitez saw John Arne Riise as a more valuable player, and decided against moving for the Welsh teenager.
It proved a calamitous mistake in the long-term, Bale went onto sign for Tottenham, where he blossomed into a superstar - and is currently the world's most expensive player, sold in 2013 to Real Madrid for £86 million.
The situation ends well for Benitez, who is now in charge of Real, and has Bale to lead his attack as he bids to win trophies in Spain.
Benitez can console himself that he was not the only Premier League manager to snub signing Bale, with both Arsenal and Manchester United making similar misjudgements.
Arsene Wenger told The Telegraph in 2013 he had made a 'huge mistake' not signing Bale, and allowing him to star at their North London rivals instead, despite tracking his progress at Southampton, the club which he signed Theo Walcott, Alex Oxlade-Chamberlain and Calum Chambers from.
Sir Alex Ferguson also told The Telegraph in 2013 that Bale was 'the one who got away', missing out on the natural successor for Ryan Giggs. SkySports reported in the summer that United were interested in signing him from Real, but it would take a costly world record fee.
Spurs have their own reason for regret though, Harry Redknapp told The Guardian recently how he blew the chance to sign Luis Suarez for the club, only to see him later sign for Liverpool and go onto become the league's best, and most controversial, player.