Liverpool's craziest winter transfer deadline days

Liverpool's craziest winter transfer deadline days - £57.8m forwards and emergency defenders

Winter might not always be the busiest time for Liverpool FC transfers, but there have been a few wild deadline days over the years

Liverpool look set to let another winter transfer window pass with no major permanent incomings, although discussions are ongoing for a loan move for Lutsharel Geertruida.

That move comes after Jeremie Frimpong was the latest to be struck down by the defensive injury curse, picking up a suspected groin complaint just four minutes into the 6-0 hammering of Qarabag at Anfield on Wednesday night (Jan 28).

But Arne Slot has so far stuck to his guns, reaffirming Liverpool's long-term approach under owners FSG. Speaking to the press after the game, Slot said: "We as a club always make smart decisions. We not only look at the short-term but the long-term. That's why we sign young players, who can develop.

"It always depends on if there are players that are available that we think can help us. If they are, can we afford them? And is this to be helpful for the longer-term future, because our players come back from injury as well.

"We have to do smart things for the near future and the longer future."

In other words, Liverpool fans should prepare for a fairly quiet deadline day, but it hasn't always been thus. Here, we'll explore three memorable winter transfer deadline days that will live long in the memory.

2006/07

Liverpool were in something of a transitional phase in the 2006/07 season, having finished third and won the FA Cup the previous season, but seeing their Champions League defence fail at the round of 16 with a 3-0 aggregate defeat to Benfica.

Ahead of the new season, Rafa Benitez brought in Craig Bellamy, Jermaine Pennant, Fabio Aurelio, Dirk Kuyt and Gabriel Paletta, as the Reds' squad underwent an overhaul with established names like Didi Hamann, Fernando Morientes and Djimi Traore making way.

This would also be the final season at Liverpool for Jerzy Dudek and Luis Garcia, while legendary striker Robbie Fowler would only manage six league starts in his final season following his return to Anfield.

The season started inconsistently, with a crushing 3-0 defeat at Goodison followed by a 1-0 loss at Stamford Bridge. A disappointing 2-0 loss away to Bolton Wanderers followed before the end of September.

The Reds found much more consistency throughout December and January, however, winning nine of their 10 Premier League games ahead of a dramatic transfer deadline day: Jan 31 2007.

Liverpool wrapped up Alvaro Arbeloa's signing in a relatively straightforward manner compared to their other major signing on deadline day.

Arbeloa joined from Deportivo La Coruna for £2.6 million as competition for Steve Finnan, with fellow Spaniard Francis Duran joining the academy from Malaga - also on deadline day.

While Duran never represented the first team at Liverpool, ultimately retiring at the age of just 26, Arbeloa went on to make 98 appearances for the Reds, replacing Finnan in the Champions League final later that year and taking his starting berth from the following season.

Liverpool's other major signing was significantly more complicated.

In a story that goes back to the previous summer, top clubs across Europe were alerted to the situation of Argentine midfield destroyer Javier Mascherano after his performances in the 2006 FIFA World Cup, but it was West Ham United that wrapped up the double signing of Mascherano and Carlos Tevez from Corinthians just before the summer window closed.

Resembling an early experiment into what would later become multi-club ownership, the double deal was controversial at the time as both players were actually owned by third party companies - all with the involvement of businessman Kia Joorabchian.

Joorabchian's company Media Sport Investment (MSI) had pumped millions into Corinthians, working with Joorabchian's other companies to finance a glut of signings in return for a majority share of profits.

However, the finances involved were unusually opaque, with Brazilian lawyers finding offshore accounts had been used to carry out transactions - attracting allegations of money laundering.

After the signings of Tevez and Mascherano, MSI announced discussions into a takeover of West Ham, which was ultimately unsuccessful.

Pressure had started to mount on MSI and Joorabchian, and an arrest warrant was issued for him in Brazil the following year, though the charges were ultimately dropped and the group absolved of wrongdoing in 2014.

During the months following the double signing, West Ham's form suffered, and the Premier League opened an investigation into the nature of the deals given that West Ham had not fully disclosed the ownership rights of the players involved.

The fear was that the third-party companies' involvement would have an influence on West Ham's sporting and financial decisions, giving Joorabchian an inappropriate level of control over the club.

Mascherano was on the fringes in the first half of the season, with suspicions that financial clauses could be influencing team selection.

This opened up an opportunity for Liverpool, who requested clearance from FIFA to take Mascherano on loan from the Hammers - or, more accurately, from MSI - on Jan 16 2007.

It took over two weeks for FIFA to clear the request on deadline day, but even then the Premier League refused to decide whether the Argentine would be permitted to play for Liverpool in the light of the furore around his ownership.

The other issue was that Mascherano had already played for both Corinthians and West Ham that season, with FIFA prohibiting a player from paying for more than two clubs in the same season.

Finally, on Feb 20, the Premier League permitted Liverpool to register Mascherano, who at last made his debut against Sheffield United four days later.

Voted Man of the Match in the 2-1 Champions League final defeat to AC Milan, Mascherano locked down a place in Liverpool's midfield and never looked back, with Liverpool eventually securing his full rights from MSI in 2008 before a transfer to Pep Guardiola's all-conquering Barcelona side in 2010.

Winter deadline day 2006/07 was also the day that sovereign wealth fund Dubai International Capital (DIC) pulled out of a deal to take over ownership of Liverpool, allowing asset-stripping private equity-investors (to put it kindly) Tom Hicks and George Gillett to purchase the club from David Moores the following week.

2010/11

Probably the most memorable of all of Liverpool's winter deadline days, the 2010/11 winter transfer window came to a close on January 31, 2011.

Liverpool were in turmoil in the 2010/11 season. The Hicks and Gillett takeover had proven disastrous, with protests erupting as early as 2008 after it emerged the pair had essentially mortgaged the club to complete the purchase.

In the midst of what has been described as a civil war between ownership and fans, Liverpool crawled to a seventh place finish in the 2009/10 season, a drastic drop-off from the title challenge of the previous year.

Rafa left by mutual consent at the end of the season, with Roy Hodgson chosen as his replacement. But the situation only got worse, with Hodgson wildly unsuited to the role and debt nearly forcing the club into administration in October 2010.

New England Sports Ventures (NESV), now Fenway Sports Group (FSG), then bought the club for just £300 million, finally freeing Liverpool from the parasitic ownership of Hicks and Gillett.

But the writing was on the wall for Hodgson, who lasted just six months in the job he was given in July 2010, replaced by Kenny Dalglish on an initial caretaker basis on Jan 8.

This was hardly a stable situation in which to enter the transfer window, to say the least. Liverpool were mired in twelfth place following Hodgson's sacking, and it took until Dalglish's fourth game in charge for Liverpool to win.

Liverpool had been tracking a young Uruguayan striker at Ajax by the name of Luis Suarez, who was earmarked as a potential partner up top for star striker Fernando Torres.

Suarez had scored a whopping 35 goals in 33 Eredevisie games the season prior, but had been suspended in November for biting PSV's Otman Bakkal.

Liverpool made contact alongside several other European clubs, and were preparing a bid when news arrived that would prove era-defining for the club.

On Jan 27, Chelsea submitted a £40 million bid for Torres. The initial bid was rejected by Liverpool, but El Nino's head had already been turned.

Torres submitted a transfer request the following day, leaving Liverpool with three days to complete a late scramble to find a replacement.

Newcastle striker Andy Carroll, who had scored against Liverpool the month prior, was the man identified. Carroll had just signed a new five-year contract at Newcastle, making a deal for the big Geordie expensive to say the least.

Liverpool went ahead with a club record £22.8 million bid for Suarez the same day Torres submitted his transfer request, which was accepted by Ajax.

But the Reds weren't done there.

A £30 million bid for Carroll was submitted early on deadline day - which already would have made him Liverpool's most expensive signing of all time - but rejected by Newcastle.

Suarez's signing, meanwhile, was confirmed when the Uruguayan put pen to paper on a five-and-a-half-year contract on Jan 31. El Pistolero would go on to fire Liverpool to the brink of a league title and - for all his many personal flaws - has a strong case to be considered the most talented player to ever wear the Red shirt.

Carroll, however, was a gilded flop. Newcastle accepted a £35 million bid later on deadline day, making Carroll by far Liverpool's most expensive signing and the most expensive English player of all time.

Despite memorable moments including a late headed winner against Everton in the FA Cup semi-final at Wembley, Carroll was never quite suited to Liverpool, and only managed to score 11 goals from 58 appearances.

Oh - and disastrous Hodgson signing Paul Konchesky left on loan to Nottingham Forest.

2020/21

A very different, and much lower-spending, deadline day than the one previously discussed, but nonetheless a dramatic one.

In a situation very reminiscent of the one Liverpool currently find themselves in as the 2025/26 winter transfer deadline approaches, Jurgen Klopp's Premier League title defenders experienced a near total collapse in the pandemic-affected season of 2020/21.

The league season kicked off much later with the previous season having been delayed during the first lockdown. It was a season of football few like to think back to - with no fans in the stadiums, Premier League football was an eerie affair.

Lest it be ignored, as well, the pandemic season was also a time that separated regular match-going fans from a central part of their lives, keeping friends apart and upending routines as nothing was the same.

This certainly applied to Liverpool's form, too, which hurtled off a cliff at the turn of the year after Joel Matip was ruled out with a groin injury.

Liverpool had already lost the talismanic Virgil van Dijk to a season-ending ACL injury inflicted by a horrendous challenge from Everton goalkeeper Jordan Pickford - one that was ignored by the VAR on the day, disgraced former referee David Coote.

Joe Gomez also suffered an ACL injury on England duty in November. Liverpool had sold Dejan Lovren in the summer, leaving the Reds with just one senior centre-back after just two months of the season had passed.

Somehow, despite the total anomaly of a 7-2 defeat at Villa Park in October, Liverpool performed well in the first half of the 2020/21 season - albeit not quite at the standards of the previous year - and sat pretty at the top of the tree on Christmas Day.

But the defensive injury crisis would have a delayed, catastrophic, effect. Jurgen's Reds went into their first match of the new year with a centre-back pairing of Jordan Henderson and Fabinho, and went down 1-0 to ninth-placed Southampton.

A third-round FA Cup win against Villa followed, but Liverpool failed to win any of their next three games in all competitions. Still, no movements were made in the transfer window, with Klopp relaying the message that Liverpool would not be forced into a panic buy.

The final straw was to arrive, however, with just three days of the transfer window remaining. Joel Matip, making his return from an complaint that had ruled him out for the FA Cup defeat to Manchester United, only lasted 45 minutes against Tottenham Hotspur after rupturing ligaments in his ankle.

Only then, with no established centre-backs available for the remainder of the season, did Liverpool act. As the clock ticked over to deadline day (Feb 1), the club hierarchy compromised by executing a pair of low-cost transfers to plaster over the gaping wound in the defence.

Ben Davies, a relatively unknown centre-back from Preston North End, was drafted in on an undisclosed fee believed to be in the region of £500,000.

To facilitate the deal, Liverpool sent Sepp van den Berg in the opposite direction on a loan deal until the end of the season. While van den Berg is now an established Premier League regular with Brentford, Davies never made an appearance for Liverpool.

The other player to come in was Ozan Kabak, a young defender who had been a regular in a generationally underperforming Schalke 04 side that was ultimately relegated.

Both were transfer stories worthy of a Hollywood movie, but neither of them made a lasting impact.

Kabak was well-known to Klopp, having played under the manager's best friend (and best man) David Wagner at Schalke. The Turkish defender had been linked with Liverpool ahead of the transfer window, and was brought in on an initial loan with an option to buy for £18 million.

Takumi Minamino was another player to move on deadline day, joining Southampton on a loan until the end of the season.

By deadline day, Liverpool were third, and a run of four successive Premier League defeats - culminating with Everton's first win at Anfield since 1999 - left the Reds in seventh.

But a makeshift concoction of Fabinho and the academy duo of Nat Phillips and Rhys Williams ultimately saw Liverpool through at centre-back, clinching fourth place on the final day with a 2-0 win over Crystal Palace - but not before Alisson kept the Reds in the fight with a heroic last-minute winner against West Brom.

The refusal to buy a centre-half who could be a realistic medium to long-term option was a source of frustration for supporters, but it ultimately allowed Liverpool to buy Ibrahima Konate in the summer, who went on to form Liverpool's next title-winning defensive partnership alongside Virgil van Dijk.

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