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#3 Robbie Keane (19 appearances for Liverpool)
Liverpool’s recent success in the transfer market has been spoken about on countless occasions, with their moves for the likes of Virgil Van Dijk, Alisson Becker and Andrew Robertson coming in for huge praise.
However, back in 2008, the Reds made a big-money move for one of the Premier League’s top strikers only to have the wool pulled over their eyes by rivals Tottenham Hotspur.
Irish international Robbie Keane – one of the most well-travelled footballers of all time – had been with Spurs since a £7m move from Leeds in 2002.
In the six seasons that followed, he’d scored 80 goals for Spurs in 187 Premier League appearances, finishing as their top scorer on four occasions.
However, in the summer of 2008, Keane became unsettled in north London, and Liverpool promptly swooped in. Despite Tottenham filing a complaint about the Reds’ conduct, Keane moved to Anfield in a £19m deal shortly after.
Despite the Irishman stating his enthusiasm as a lifelong Liverpool fan, he simply couldn’t fully break into the Reds’ first team, largely due to the form of Fernando Torres.
Keane made just 19 Liverpool appearances, scoring five goals. In the summer of 2009, just a year after leaving, he headed back to Tottenham for just £12m.
Essentially, Spurs made a £7m profit at Liverpool’s expense, all for the want of an unsuccessful season that’s now largely been forgotten by Liverpool fans.
#4 Mauricio Pellegrino (12 appearances for Liverpool)
Mauricio Pellegrino is largely remembered by Premier League fans for his unsuccessful spell as manager of Southampton in the 2017-18 campaign.
The Argentine arrived with much fanfare after a successful run in charge of Alaves but was fired by the Saints after a horrific run of one win in 17 matches.
However, prior to his career as a coach, Pellegrino was a successful player at the top level for around 16 years, even playing for Barcelona at one point.
His greatest successes came with Valencia, who he helped to two La Liga titles as well as the 2004 UEFA Cup.
More forgettable, however, was his short stint as a Liverpool player in the 2004-05 season.
Pellegrino moved to Anfield in January 2005 on a free transfer, joining his former Valencia boss Rafa Benitez at Merseyside.
The move made him the first Argentine to play for Liverpool, but his tenure did not last long. Pellegrino made just 12 appearances in the Premier League for the Reds and completely failed to make an impact.
He even missed out on Liverpool’s Champions League triumph in May 2005, due to being cup-tied for the campaign after appearing for Valencia.
Pellegrino was released that summer, and his run as a Red has since been forgotten. However, he did make another kind of mark on the club later on - as the manager who sold Virgil van Dijk to Liverpool in 2018!
#5 Nuri Sahin (12 appearances for Liverpool)
Turkey international Nuri Sahin came to Liverpool with plenty of hype after winning multiple trophies with Borussia Dortmund and Real Madrid.
However, to say his tenure at Anfield was disappointing would be a huge understatement.
Sahin first broke through at Dortmund in the 2005-06 season, becoming the youngest player to ever play in a Bundesliga game upon his debut.
He went on to spend five seasons with the German club and saw his greatest success in the 2010-11 season. That campaign saw him make 30 appearances as Dortmund won the Bundesliga title.
His performances were so good that he was named the Bundesliga’s Player of the Season. He subsequently found himself on the radar of Real Madrid, who paid €10m for him in the summer of 2011.
However, despite winning a La Liga title with Real Madrid in his first season there, injuries restricted him to just four appearances. So when he was loaned to Liverpool for the 2012-13 season, hopes were high amongst Reds fans that he’d recapture the form he showed in his Dortmund days.
That wasn’t the case, though. Still struggling for fitness, Sahin did manage three goals and three assists for the Reds but only appeared in 12 games. In January 2013, Liverpool decided to cut his loan move short.
Sahin ended up back at Dortmund, and in the years that have followed, his unfortunate stay at Liverpool was almost entirely forgotten.
