This is a long read, it looks back to our transfer dealings from the Summer of 2008 to today. More than anything IMO, our complete ineptness in the market during those 4 years- along with cost cuttings at certain key moments- have led to us now becoming a mid table club.

Summer of 08:
This window would be crucial for several reasons. First off, it was the last time Rafa Benitez would have a negative net spend in the transfer market. After this Summer, he would no longer be able to buy players without selling some first. Secondly, it would be the first example of catastrophic transfer decisions under Benitez which would greatly impact on future team performances. Up until this Summer, Rafa had generally been fantastic in the transfer market, extracting good value low cost deals (Garcia, Reina, Agger, Skrtel, Arbeloa) as well as being spot on when spending big money (Torres, Mascherano). The Summer of 2008 saw Rafa’s judgment go awry- and the first time a Liverpool fanbase vehemently opposed a proposed Benitez transfer swoop. With the team go so close to the title after that Summer, it looks now more than ever that it was a real opportunity lossed- and the start of the decline.
With a spine as strong as any other club in Europe (Reina in goal, 2 of Skrtel, Agger, Carragher or Hyypia in defence, Alonso and Mascherano in midfield and Gerrard playing off golden boy, Fernando Torres), it was a widely held view that Liverpool needed to strengthen its wings.

Instead, this summer proved to be an absolute disaster and the precursor for all the mess that would come during the next 4 years.
For 3 months, Rafa Benitez chased Gareth Barry. A versatile player that had come off a very good season in the center of midfield at Aston Villa. The chase for Barry (whose added value in Rafa’s eyes was that he “could play in 3 positions”) led to Xabi Alonso being touted all across Europe.
As the Barry chase stalled, Rafa set about reinforcing other positions in the team. John Arne Riise was sold, replaced by Andrea Dossena. David Ngog, a young kid from France, was snapped up as was Diego Cavalieri, yet another foreign backup goalkeeper.
But it was the signing of Robbie Keane that grabbed all the headlines. At 18m, he was Liverpool’s 2nd biggest signing. A striker who’d excelled at Spurs next to Dimitar Berbatov, it was thought that he would partner Torres in attack- meaning that the famed Gerrard- Torres partnership would be split with the captain being moved further back.
Instead of focusing on improving the weak areas out wide, Liverpool had so far seemed largely focused on altering its world class spine.
Just before the start of the season, Liverpool welcomed Lazio for a pre season friendly. The game, uneventful as friendlies are, saw the Kop telling its manager exactly what they thought about the proposed Alonso sale- and where he could stick the idea of replacing him with Gareth Barry.
A couple of days later, empowered by the fans’ voice, the owners refused to sanction a bigger bid for Barry and Benitez’s plan to link Barry up with Keane died.
On the last day of the window, Rafa snapped up Albert Riera- a left winger who would take Harry Kewell’s place in the squad.
January 09:
Liverpool’s title bid was faltering as they drew 3 league games in January before beating Chelsea on the before last day of the window.
The next day, Robbie Keane was sold back to Spurs for 12m. The Reds had lost 6m on Keane in 6 months.
Keane had not settled well at Anfield and had not done enough to warrant a 1st team place. More to the point, Liverpool were not in a financial position to keep an expensive player like Keane on the bench and let his value depreciate. It was decided that it would be better to bring the money in rather than let Keane’s value decrease further.
For a while, Keane was regarded as Liverpool’s worst ever signing. More pertinently though, the Reds bought no one to replace him.
Liverpool (still fighting on 3 fronts) were expected to see out their first title chasing season in 7 years with only Torres and Ngog as its main strikers.
On the same day Keane moved back to Spurs, Andrei Arshavin moved to Arsenal for a similar fee. The tiny Russian would later have a telling say in Liverpool’s title bid.
Summer 09:

The Reds had come as close to their 19th league title as at any time since 1990, finishing 4 points away from top position.
This should have been a summer where they reinforced their squad to make the final push to their mythical number 19.
Instead, it became the end of the dream and the final nail in the Hicks and Gillett coffin.
The reds lost the inspirational Sami Hyypia for free that summer along with the dependable and versatile Alvaro Arbeloa for a pitiful 3m to Real Madrid.
Arbeloa was replaced early in the window by Glen Johnson. Under pressure from City and Chelsea, the Reds coughed up 17m for the Portsmouth full back- still a British record transfer fee for a full back.
But it was the departure of the team’s metronome, XabiAlonso, which would most hurt the Reds.
Alonso, off the back of a fantastic season, had decided to move back to Spain and join the Galacticos v2.0 project. The Reds spent all summer trying to extract the best possible deal from Real Madrid, meaning they missed out on Rafa’s preferred Xabi replacement: Gareth Barry, who moved to Man City.

A few days before the season kicked off, Liverpool accepted a 30m bid for Alonso- and swiftly moved to acquire Alberto Aquilani to replace him.
The 18m Italian was seen to be a potential star in world football- but had suffered terrible injury problems during his last 3 seasons and had barely played at Roma. He arrived at Anfield injured and wouldn’t start a league game until winter. It would prove to be one of the 2 biggest transfer mistakes in the history of Liverpool Football Club.
Later that summer, Rafa snapped up a cut priced Soto Kyrgiakos to replace Sami Hyypia.
There would be no more money made available to him.
Rafa was given a 20m budget- but was later told that included wages for current players too. There would be no backup striker to replace Robbie Keane. Instead, the Reds recalled Andrei Voronin from loan. There would be no David Silva (who was rumored to have been lined up by Benitez).
There would be no squad reinforcement.
And, there would be no more title chases.
Winter 10

Andrea Dossena (who was supposed to replace John Arne Riise) was shipped back to Italy and Andrei Voronin sent to Russia.
Maxi Rodridguez was brought in a on a “free” transfer from Atletico Madrid.
Rafa had a posittive net spend for his last transfer window, despite the Reds looking like they were going to miss out on champions league qualification. There was no emergency funds released to help the Reds get the 4th spot.
And there would be no more 4th spot. Instead, Liverpool finished 7th and Benitez was promptly fired.
Summer 10

With Rafa gone, Roy Hodgson was brought in. Along with Christian Purslow, the pair would combine to make some more disastrous moves into the transfer market.
In one of the most suicidal free transfers in football history, Purslow secured Joe Cole on a 100,000k a week contract. The irony was that Cole had signed on those terms for near bankrupt Liverpool after being released by billionaire run Chelsea, who had found his wage demands ludicrous.
The mercurial Yossi Benayoun, one of the few creative players in the Reds squad, went the other way for 5m. Hodgson moved quickly to buy one of his ex players, 30 year old Christian Poulsen (voted Juventus’ worst player of the century by the Old Lady fans).
In another free transfer that cost the Reds a fortune, Milan Jovanovic (brought in by Rafa Benitez) arrived- a forward player who was asked to replace left winger Albert Riera. Benitez was also responsible for the arrival of Jonjo Shelvey from Charlton.
But it was the exit of another member of the Reds vaunted spine that grabbed all the headlines. Javier Mascherano, after having wanted to leave the previous summer, joined Barcelona for 18m. A couple of days later, Raul Meireles arrived for 12m on low wages- but with a promise he’d get a pay rise should he have a good season.
The central midfield area could have been weakened further as Purslow tried his upmost to flog Lucas Leiva, but the Brazilian saw out the Summer. Hodgson had better luck with Aquilani, as Rafa’s replacement for Xabi Alonso was sent on loan to Juventus: one injury riddled season into his Liverpool career.

It’s the club’s dealings on the last day of the window that summed the insanity of the Hodgson-Purslow alliance. With Emilio Insua packed off to Turkey on loan, the Reds had already resigned the constantly injured Fabio Aurelio on a 2 year deal. But they still needed a first choice left back.
Enter Hodgson. He moved for another one of his ex-players, Paul Konchesky. Liverpool paid 5m for the 29 year old English journeymen- and sent 2 bright young talents Fulham’s way too- another transfer deal that reeked of utter supidity and lack of forward planning.
Only Luke Young’s desire to stay in the midlands prevented Hodgson from signing another journeyman English full back while in attack, there was still no replacement for Robbie Keane- 18 months on.
January 11
The month started with Roy Hodgson‘s firing- and the arrival of Kenny Dalglish as caretaker manager.
Hodgson had led the Reds through 5 months of the worst football seen at Anfield in decades. His signings, especially Konchesky and Poulsen, became the symbol of the utter mediocrity that blighted his spell as Liverpool manager.
Dalglish came in and almost immediately, new Liverpool DOF Damien Comolli, under the watchful eye of new owners FSG, set about buying Luis Suarez from Ajax. After weeks of negotiations and years of scouting, Suarez was signed for 22m.

Finally, 2 years on, Liverpool had signed a replacement for Robbie Keane. Suarez would pair up with Fernando Torres in attack and Reds fans were buzzing.
But only for a few hours.
On the evening the Suarez deal was confirmed, Chelsea had a bid rejected for Torres. The next night, 3 days before the Winter window closed, Torres put in a transfer request. The board rejected it.
It quickly became clear, however, that we were going to sell him. A figure of 50m (rumored to be the buyout figure clause in Torres’ contract) was muted. The focus switched to what business we could do in the final couple of days of the transfer window in order to replace him.
FSG, very mindful of the fact that selling a fan’s favorite in their first transfer window after replacing the hated previous owners could create mutiny, gave carte blanche to Damien Comolli to sign a replacement.

On the morning of the 31st of January 2012, Liverpool had a ludicrous 30m bid for Andy Carroll amazingly rejected by Newcastle. Carroll, a young English towering target man, was just about the antithesis of Torres in every single way possible. After scouting Suarez for years and planning to play him with Torres, the Reds completely ripped the plan apart by going for a completely different type of player in Andy Carroll.
With hours left of the window remaining, to the utter incredulity of millions of football fans around the world, Liverpool upped their bid for Carroll by 5m and signed their man- who was injured at the time. Torres then dully signed for Chelsea for 50m, the latest piece of the 2008 spine to depart.
The Carroll deal would prove to rival the Aquilani in the worst ever stakes. Concurently, it gave selling clubs full ammunition to make Liverpool overpay for their targets. It also signaled a desire from FSG and Damien Comolli to target young English prospects with premier league experience.
Summer 11

Carroll had very little impact during the end of his the 2010/11 season, as the Reds put together their best run of form since their title chase in 2009.
Instead, led by the magnificent Luis Suarez, Kenny Dalglish’s team set about playing a fast tempo, high octane attacking game with Maxi, Meireles and Dirk Kuyt all interchanging positions around the new number 7.
The challenge to Dalglish was how to incorporate Carroll into the side. But with funds promised by FSG, fans were as optimistic as ever before that Kenny would lead the team to glory.
What transpired during that summer, however, would lead to Dalglish and Comolli losing their jobs, fans losing hope and FSG changing their entire approach to running a football club.
The summer kicked off with Liverpool parting with 16m to sign Jordan Henderson from Sunderland- a young English player with potential- but who came off the back of an inconsistent season playing in a position where the Reds were well stocked in.
It was thought that Henderson would be Kenny’s new Ray Houghton, coming inside from the right. But the fee, again, was excessive and another sign to clubs that Liverpool were a soft touch in the transfer market.
Kenny then signed Charlie Adam from Blackpool for 6m, another central midfield player whose set pieces we believed would supply Andy Carroll.
After missing out on Ashley Young, Kenny signed Stewart Downing from Aston Villa. At 20m, Downing was another English player signed at an excessive price, but whose crosses from the left wing would hopefully be headed in by Carroll.

Downing would become the 3rd player signed (for a total of 42m) with the seemingly specific intention of getting the best out of Carroll. Luis Suarez, meanwhile, saw a player he linked superbly well with, Raul Meireles, on the bench for the first 2 league games.
A few days before the season started, Kenny brought in Jose Enrique to replace Konchesky at left back and later signed Sebastien Coates for 7m as a fall back option after missing out on Phil Jones.
On the last day of the window, Reds rejoiced as the likes of Ngog, Cole (on loan), Poulsen and Degen all left the club. It seemed that the club were cutting off the entire deadwood and reshaping the squad with no mediocrity allowed in. Aquilani was also gone- but again only on loan, this time to Milan.
Spirits were boosted as old boy Craig Bellamy joined on a free transfer, a replacement for Ngog who could also play on the left in the departed Jovanovic’s place. But, 30 minutes before the window close, Meireles joined Chelsea for 11m.
The promised wage rise had never arrived as FSG were reluctant to give an older player a big contract. Kenny, meanwhile, had signed Henderson, a younger player who could play where Meireles did. It made financial sense.

But, in reality, Meireles’ exit was a big blow: he had linked superbly with Suarez during the end of season run and seemed to be able to bring the best out of the Uruguayan. Indeed, in less than 40 minutes of league play, Meireles created as many goals for Liverpool in the league last season than Henderson and Downing did all year- COMBINED.
January 12

For the first time in 4 years, there were no incomings at Anfield. Despite the Reds challenging for the top 4, it had become apparent that they desperately needed a finisher.
Whether FSG had refused to sanction funds due to the lack of return from the summer signings (only Enrique had improved the first 11 while Bellamy was a great impact player) or whether Kenny decided not to delve into the market is still a matter for debate. What we do know, for a fact, is that Croatian hitman Nikica Jelavic was heavily linked to Liverpool that window but ended up signing for Everton for 5m.
Liverpool subsequently won the league cup and reached the final of the FA cup that season, but displayed relegation form in the league. A couple of months before the season ended, Comolli was fired- a damning indictment on his transfer dealings. A couple of days after the season ended, Kenny was gone too after finishing 8th, the Reds’ worst league position since 1994. The King was to be replaced by Brendan Rodgers.
Summer 12

It is, of course, too soon to make any judgments of this window but a couple of things are clear.
FSG’s transfer policy became heavily weighed into lowering the wage bill. The likes of Maxi, Kuyt (for a ridiculous 1m), Adam, Spearing (on loan), Aquilani (finally on a permanent deal- but with an expensive golden handshake) and Aurelio all left the club.
In came Fabio Borini a striker who had previously worked with Rodgers and Joe Allen, a 15m central midfielder from Swansea. The Reds also signed Oussama Assaidi, a winger, and secured the loan signing or Nuri Sahin.
But it was in the last couple of days where yet another ludicrously ridiculous set of decisions took place- demonstrating again how Liverpool are gloriously inept in the transfer market.
A day before the window close, Andy Carroll was sent on loan to West Ham. Carroll didn’t fit in Rodger’s system and as such was surplus to requirements. But no one came in with an offer to buy him and thus the men in charge, in order to again decrease the wage bill, let him go on loan.
This left Rodgers, like Benitez in 09, with only 2 senior strikers- but, unlike Rafa, with no Dirk Kuyt anymore to fill in as 3rd option.
With the owners refusing to stump up the money for Clint Dempsey, mindful of his age as well as resale value and unwilling to continue overspending for players, Liverpool started looking for other alternatives.
Erringly like the Konchesky deal in 2010, the Reds attempted to sacrifice a young player in order to acquire a 29 year old from Fulham. 16m Jordan Henderson was offered to the London club in exchange for a player in the last year of his contract who would, later on in the day, move for 6m.
Henderson refused to leave the club.FSG refused to release more funds. And Fulham refused to budge.
With negotiations at a standstill, Rodgers lost Dempsey to Spurs- leaving him with only 2 senior strikers and the choice of free agents like Michael Owen in case he wanted a 3rd.
Liverpool now have 1 point from the opening 3 league games and the smallest squad in their recent history.
They have picked up 19 points from their last 22 league games, 0.86 a game. Over a 38 game season, that gets them around 33 points-
Not enough to stay in the premier league.