#3 Philippe Coutinho
Brazilian attacking midfielder-cum-winger Philippe Coutinho had established himself as Liverpool’s most important player at the time of his departure. Coutinho featured 201 times for the Premier League club and played a direct hand in 99 goals. The “Little Magician” was known for his nimble feet and long-range strikes.
Coutinho managed to strike a connection with the fans at both club and national level and it was just a matter of time before he made the big move. Barcelona splashed the cash, €135 million to be exact, to woo Coutinho to Camp Nou. However, the fairytale soon turned into a nightmare.
Coutinho’s failure at Barcelona can be attributed to him being played out of position, Barcelona’s mismanagement, and his poor performances. Jurgen Klopp warned the Brazilian international against leaving Anfield. While the 28-year-old still has time to revive his career, it is safe to say that he repents for not listening to the German manager.
#2 Fernando Torres
During his Liverpool days, Fernando Torres caused sleepless nights to many-a-defender, just ask Nemanja Vidic. He was one of the best strikers in the world and managed a podium finish in the Ballon d’Or back in 2008.
In search of trophies, Torres joined Chelsea in 2011 for what was a British record transfer fee back then.
Torres had built a deadly partnership with Liverpool legend Steven Gerrard while at Anfield. The Spanish striker was adored by the Kop, who relentlessly sang his name.
He shocked the entire world when he decided to move to one of Liverpool’s rivals and soon became an extremely disliked figure in and around Merseyside.
The serial goalscorer at Liverpool found it hard to find the back of the net while at the London-based club. Although Torres won the UEFA Champions League and the FA Cup at Chelsea, his career went on a downward spiral after parting ways with Liverpool. Torres has publicly stated that he regrets the way he left the club.
#1 Michael Owen
Michael Owen is yet another striker who rued his Anfield departure. He was a key figure in Liverpool’s cup treble-winning campaign, a fruitful year that culminated with his Ballon d’Or triumph in 2001.
To this date, Owen remains the only Liverpool player to get his hands on the prestigious individual award. Overall, he scored 158 goals in 297 matches for his boyhood club.
Owen left Liverpool to join Real Madrid as he was fascinated by the mere thought of representing a club of Los Blancos' stature. He also relished rubbing shoulders with the likes of Zidane and Ronaldo.
His stay in Madrid lasted just one year, and the Chester-born footballer was back in the Premier League with Newcastle. Owen’s reputation among Liverpool fans was damaged even further when he moved to Manchester United in 2009.
The footballer-turned-pundit witnessed his goal tally diminish after his move away from Liverpool. To make matters worse, Owen also had to watch his former team-mates lift the UEFA Champions League just one season after he left them.
Owen was never the same after joining Real Madrid, and it is no surprise that he regrets that decision.