The January transfer window is often a lot more challenging for club directors and coaches to navigate as the potential to waste money is drastically heightened.
Players tend to cost more and quick decisions need to be taken when an opportunity arises to try and improve the squad. The summer is when signings that were planned a long time ago are made, but January is when opportunistic and sometimes desperate moves are made.
Here is a look at some of Liverpool's worst ever January transfers over the years.
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10. Takumi Minamino
Japanese attacker Takumi Minamino arrived at Liverpool from RB Salzburg for £7.65m in January 2020 and it would be harsh to say that he was a failure at Liverpool.
He scored a handful of goals but ultimately never held down a starting role under Jurgen Klopp. He has since been moved on to AS Monaco. Not a bad signing, but didn't quite pan out as hoped.
9. Ozan Kabak
Ozan Kabak was an emergency signing in 2021 when every central defender within the vicinity of Anfield got injured. That being said, he was already fairly highly-rated young defender and there was scope for his loan to be made permanent.
Whilst he was beneficial for being able to literally put defenders on the pitch, Kabak did not impress and was not kept by the Reds.
8. Ben Davies
Much like Ozan Kabak, Ben Davies was an emergency signing in 2021 to get defenders into the squad. He never made any sort of impact and after a loan spell at Sheffield United, he then got sold to Rangers.
Amazingly though, Liverpool made an almost £2.6m profit on the player they signed from Preston.
7. Marko Grujic
Marko Grujic joined Liverpool in 2016 but he has only ever made 16 appearances for the club. He has been on loan at four different clubs and was eventually sold to Porto in 2022 for a €2m profit.
6. Fernando Morientes
Fernando Morientes arrived at Liverpool in 2005 for £6.3m from Real Madrid and it was expected that he would make a big impact.
His quality was never really doubted but he just could not seem to make it work in a red shirt. He got 12 goals in 61 Liverpool games.
5. Rigobert Song
Rigobert Song joined Gerard Houllier's Liverpool in 1999 from Salernitana and whilst he had some steady spells in the first team, he was then phased out by the coach and became an unused resource.
He lacked the tactical intelligence needed to play at the top level which meant his impact at Liverpool was minimal.
4. Jan Kromkamp
Arriving after a straight swap with Josemi, Jan Kromkamp never got close to imposing himself on Rafael Benitez's Liverpool squad and could not out Steve Finnan from his position.
He was there for 18 months before being swiftly shipped out again and quickly forgotten.
3. Abel Xavier
If you sign a player from your local rivals, you want them to do well and show what the rivals are missing. That wasn't the case for Abel Xavier, who joined Liverpool from Everton in 2002.
He had no impact in his 14 league appearances and Liverpool were made to look a bit daft having given Everton £800,000 for him.
2. Steven Caulker
Having just been relegated with QPR, Liverpool decided that Steven Caulker was the right player to add some depth to the defence.
He went on to play four Premier League minutes for Liverpool in six months and that was the end of that. He was shipped out again and everyone was left feeling a bit confused.
1. Andy Carroll
Only one man was ever going to top this list. Having sold Fernando Torres for £50m, Liverpool gave £35m of that to Newcastle United for Andy Carroll who had been in superb form.
He scored 11 goals in 58 appearances for Liverpool before being sold for €17.5m to West Ham United.