10) Loris Karius
Voted second-best Bundesliga goalkeeper behind Manuel Neuer in 2016, Jurgen Klopp struck a cut-price £5m deal with Mainz to bring Karius to Liverpool .
What could go wrong, then?
Quite a lot, in all fairness, with an error-strewn first campaign followed by Klopp's decision to reinstate Simon Mignolet to the starting XI.
After winning back his place the following campaign, Karius' Kiev nightmare occurred and he was shipped out on an eventful two-year loan to Turkish outfit Besiktas.
9) Charlie Adam
Jamie Carragher once claimed Adam left Steven Gerrard fearing for his place at Liverpool, but the legendary captain's concerns were wholeheartedly misplaced.
A £7m signing from relegated Blackpool – months after failing with a bid in January – then-boss Kenny Dalglish was enthused by the long-term prospects of his new capture.
"We're looking forward to Charlie being a success here,” the Reds legend said.
“He made a huge contribution to Blackpool's team last year and we're looking forward to him making the same contribution here.”
12 months later and Adam signed a four-year deal with Stoke City with Liverpool taking a small financial hit.
8) Joe Cole
Impressive for a free agent to make such a list but Cole's time at Liverpool was nightmarish after becoming Roy Hodgson's first signing at Anfield.
Rumoured to be earning in the region of £90,000-per-week at Anfield, 26 Premier League appearances was enough to convince Brendan Rodgers that this was a player on the wane.
"I can only play for teams that I'm passionate about and I think that's what went wrong for me at Liverpool," Cole later said.
"I didn't feel a connection with the club or the place that I had at Chelsea and West Ham.”
7) Christian Poulsen
Another Hodgson signing but absolutely the same result.
Quickly replaced by Jay Spearing in the team following the arrival of Dalglish as manager, the Danish midfielder joined Evian 12 months after signing for Liverpool.
The writing was perhaps on the wall for Poulsen when, somewhat hysterically, Hodgson said following a draw with Wigan: “He's not that bad on the ball, but let's not beat about the bush and try to disguise the fact – he's had a bad start."
6) Mario Balotelli
Super Mario's time at Liverpool was as short-lived as it was underwhelming.
Weeks after denying he would make a move for the Italian striker, Rodgers plumped for Balotelli over experienced former Barcelona star Samuel Eto'o.
The transfer gamble did not come off and Balotelli ultimately ended up scoring just one Premier League goal for the Reds,
Other moments including refusing to clap the travelling Reds supporters or partake in a warm-down ensure he is not remembered fondly at Anfield.
5) Fabio Borini
"I'd anticipate that over the next two or three years he'll really progress and I'm sure do very well for Liverpool,” Rodgers said after making Borini his first signing in 2012.
"Fabio fits the model of what we're trying to do in building not only for now, but also for the future.”
38 games and three goals later in all competitions, the £11m former Chelsea talent is currently entering his third season with AC Milan following a spell at Sunderland.
4) Stewart Downing
Downing was a regular fixture in the Liverpool side after joining under Kenny Dalglish in 2011 and Brendan Rodgers kept faith in the winger the following season.
Despite being one of England's most established stars at the time of his arrival at Anfield, however, the £20m man failed to live up to expectation and was eventually moved on to West Ham United.
He registered three goals and seven assists in more than 50 Premier League appearances for Liverpool.
3) Paul Konchesky
If making 15 Liverpool appearances before being moved onto Championship outfit Nottingham Forest on loan wasn't bad enough, Konchesky's mum referring to supporters as 'Scouse scum' was a kick in the teeth for the former Fulham defender.
Following Hodgson from Craven Cottage for a cut-price fee, he managed to see out just one season of a four-year deal.
Last term Konchesky could be found playing for East Thurrock United in the National League South.
2) Lazar Markovic
From one of Europe's brightest prospects to turning out in his homeland of Serbia for FK Partizan, Markovic would be forgiven for being fairly disappointed at how the past five years have panned out.
Loan spells at Fenerbahce, Sporting Lisbon, Hull City and Anderlecht quickly followed his £20m move to Liverpool as well as a short-lived spell at Fulham.
Now 25, the winger points the finger largely at one man for a torrid time at Anfield after often being asked to turn-out at right-wing-back.
“I didn’t have a good relationship with [Rodgers],” he said. “I played in many positions but not in mine.”
1) Andy Carroll
It had to be, didn't it?
The £35m man was Liverpool's record-signing when he strolled through the doors of Anfield in January 2011 alongside Luis Suarez but failed to ever live-up to his price-tag.
A double at home to Manchester City and that memorable Wembley winner against Everton aside, Carroll's highlight reel is almost non-existent.
Liverpool would be hard-pressed to make such an expensive mistake once again.
