Since the arrival of Jurgen Klopp in 2015, Liverpool's activity in the transfer market has been something to marvel at. The likes of Mohamed Salah, Sadio Mane, and Andrew Robertson, amongst others, seem like heists in a market which has inflated a lot.
However, there was a time when the club was not really known for its acumen in the transfer window.
The Reds have made some deadly errors in the transfer market previously, which has seen them wasting a lot of money on players who never worked out for them.
The eras of Roy Hodgson, Kenny Dalglish, Brendan Rodgers etc. were marred by bad results and worse transfer signings which left fans questioning what exactly was going on at the club.
Here, we take a look at five of the worst signings ever made by the Reds:
#5 Christian Benteke - £32.5 million, 2015
Christian Benteke was not a bad striker when he came to Liverpool - in fact, he was quite clinical and had impressed a lot of people at Aston Villa.
However, the circumstances he was signed during, and the role he was expected to play made Anfield a bad experience for the striker.
Signed a year after Luis Suarez's departure, the club was still trying to replace the world-class player.
However, Liverpool did not need a target man then. They needed a more fluid striker who could create some chances for his teammates and who could move freely enough on the field.
Benteke was none of those things, and he was never going to fit into Jurgen Klopp's system, who had taken over from Brendan Rodgers midway through the season.
After 10 goals in 42 appearances, it was clear that the Belgian international was not needed by Klopp, and he was shipped off. A costly experiment which never worked out.
#4 Sean Dundee - £1.8 million, 1998
Due to his transfer fee (which was still moderately high in 1998) and his short one year stint, Sean Dundee ranks 4th on this list. Otherwise, he could very well have made the top 2.
If you do not remember Dundee at Liverpool, do not fret. His time there was as forgettable as the 2014-15 season was, a memory which Liverpool fans have chosen to block out.
“One player I do regret signing was Sean Dundee; he was terrible on and off the pitch,” former Liverpool manager Roy Evans has since told LFCHistory.net.
“He didn't take any notice of me, did what he wanted and lacked discipline. He certainly shouldn't have joined Liverpool.”
Dundee was signed as a cover for the injured Robbie Fowler, but he made less of an impact than Fowler would have made with one foot.
Dundee made five appearances for Liverpool and did nothing of significance during that time, as he battled with fitness and confidence issues.
All in all, he was one of the worst players to represent Liverpool in its storied history.
#3 Alberto Aquilani - £17.1 million, 2009
In hindsight, Alberto Aquilani's Liverpool career was a summation of the club itself during their "banter years", when the Reds suffered their worst spell of football in recent memory.
Signed from Roma, Aquilani arrived at Anfield in 2009 with some promise and was expected to take over from the departing Xabi Alonso.
Not only did he spectacularly fail at filling the Spaniard's shoes, but his performances also left the Anfield faithful dismayed more often than not. Three years (and not one great performance) later, the Italian was sold to Fiorentina for just €790,000 in 2012.
The former Roma player made 18 Premier League appearances for the club over three years. To give this some context, each league appearance cost Liverpool over £1M in terms of transfer fees and salary. The Italian was plagued with injuries and did not have a single memorable game at Anfield, and the fans were more than happy to see his departure.
#2 El Hadji Diouf - £10 million, 2002
There is perhaps no ex-player who is hated more by the Liverpool faithful than this former Senegalese international. Upon his arrival at Anfield, there was some excitement around El Hadji Diouf's ability as he had performed well for his nation in the 2002 World Cup.
He scored a brace on his debut, but then went seven months without a goal as the club's primary striker.
All the other instances in his Liverpool career are ones which fans look back at with disgust - he spit at a Celtic fan during a European game, went two full seasons goalless, and now he is prominent for hurling abuse at club legend Steven Gerrard once in a while.
In the 2003-04 season, Diouf amassed 13 yellow cards and one red card and gained a name for himself as a notorious, no-good player who was better at fouling than actually playing football.
Liverpool legend Jamie Carragher had this to say for him - "He has one of the worst strike rates of any forward in Liverpool history. He's the only no. 9 ever to go through a whole season without scoring, in fact, he is probably the only no. 9 of any club to do that. He was always the last one to get picked in training."
His departure from the club in 2005 made fans heave a sigh of relief.
#1 Paul Konchesky - £3.5 million, 2010
Every other player on this list either came in with some promise and talent or as a deputy for someone else. Paul Konchesky's signing, however, as the first choice left-back in 2010 showcases just how bad the Reds were at the time.
The former English international was clearly out of his depth at Anfield, ad put in not one good one performance for the club. An error against Spurs allowing Aaron Lennon to score the winner was the beginning of his downfall and Konchesky was sarcastically cheered by Liverpool fans when he was taken off against Wolves.
Liverpool and Konchesky were never a good fit, and his place at the top of this list is undeniable.