As the clock ticked over to 10.30 p.m. last night it seemed that any concerns about Raul Meireles switching camps to Chelsea had been unfounded.
Yet as the news came through about a late transfer request being made by the Portuguese star you couldn't help but feel your heart drop swiftly.
Within an hour it was confirmed—he had signed for his former manager Andre Villa-Booas at Stamford Bridge. Liverpool had lost a player who had brought so much energy, passion and goal scoring ability to the side since Roy Hodgson's mismanagement of the squad.
Unsurprisingly this is not the first time this century that the man in charge has let such a talent head for the exit.
Various others have come and gone before Meireles and others will no doubt follow.
Sometimes they go onto greater things and spectacular new adventures and reach the dizzying heights of which they had not found at Anfield.
At other times Liverpool are left with a disappointing lacklustre replacement and are left to pick up the pieces of what could have been.
Here I will take a look at the top 10 players from the last 11 years who have left the Kop and who are sorely missed—well by some people at least!
My honorable mention goes to former reds striker Neil Mellor who is playing well and beginning to score consistently at Preston North End.
Labelled as one of the biggest ever steals of Liverpool's transfer history, Sami Hyypia joined from Dutch side Willem in 1999 for a fee of around £2.6 million.
After catching the eye—by of all people a cameraman—he established himself firmly into a frequent defensive role at Anfield.
At certain points during his Liverpool career he managed to also earn captaincy, but it was his stubborn defensive prowess and wonderfully timed headers that gained him a legendary status at Liverpool.
His effective and consistent partnership with the likes of Stephane Henchoz proved to be a winning formula in the league. Their ability to keep goal scoring opportunities away from the opposition helped the side to consecutive low conceding seasons.
As his age delved deeper into the 30's however he lost the support of Rafa Benitez and even a spot in Europe as new regulations meant he had to be forfeited under new regulations quoting a required number of home grown players in the squad.
When he did appear in the league though, he continued to show why he was regarded as such a wonderful and inspiring centre back.
Maybe it is true that he was advancing beyond his best. Yet the biggest loss Liverpool made by letting him go was in losing a potential coach.
As a lifelong Liverpool fan, Hyypia spoke of his desire to progress to this role when his playing career ended. This is now a role he takes up in the side he transferred to in 2009—Bayer Leverkusen.
Also brought in during the 1999 campaign was Sami Hyypia's early centre back partner, Stephane Henchoz.
The celebrated Swiss international was already playing in England with Blackburn before his move to Anfield through Gerard Houllier.
Whilst not able to get his name on the score sheet like Hyypia, he was as efficient in the role. The dual role brought Henchoz many trophies with the side, including the treble of 200—as long as you forget his handball in the Carling Cup final against Birmingham which took the game to extra time.
It is worth noting that it was the emergence of Jamie Carragher that forced Henchoz out of the starting line up under Benitez. Therefore you would be hard pressed to ponder his Liverpool career had he stayed.
Yet his average returns from spells at Celtic, Wigan and a rebound back to Blackburn can't have given him much to celebrate.
Another member of the treble winning season was current Fulham stalwart Danny Murphy.
The Chester born player seemed to acquire important and pivotal early years of personal development at Liverpool. He built the reputation he is now respected for now as a gritty and determined midfielder at Anfield.
His career did start lower down the leagues at Crewe Alexandra, and it was Liverpool who beat other interested clubs to signing him in 1997. He had a topsy turvy opening—being shipped off on loan back to Crewe in only his second season at Liverpool.
Yet upon his return he gained regular first team action scoring a total of 44 goals in his 249 games for the squad. When he left for Charlton in 2004 he struggled to find the same form Liverpool fans had become to expect of him.
But it was a more promising move to Fulham where he gained captaincy that caused us to reassess what sort of a player he was. After guiding Fulham to victories over the likes of Juventus and into a Europa League final he confirmed his awesome ability.
He still remains for that reason a player who maybe we were too hasty in releasing, in the last seven title losing years.
During his last season at Anfield, former England hero Michael Owen was the highest scoring player during his time at the club.
Despite injury setbacks in the 2003/04 campaign he still managed to net 19 times in 29 games and so it was something of a surprise when he exited for Real Madrid that summer.
Gerard Houllier had left the side and pundits were quick to point out his lack of starts in European fixtures, meaning he was able to go elsewhere and compete at the highest level.
Sadly for Michael Owen, his six seasons of scoring 20 plus goals was never matched again. Real Madrid sold him to Newcastle after only one year before an unexpected move to Liverpool's fierce rivals Manchester United gave him a slight reprieve.
At Old Trafford he has been used more as a super sub but in the process has gained various winners medals and a rejuvenated career.
Had he stayed at Liverpool however you can't help but feel he would have sustained his goal scoring abilities and even edged the side closer to rivals United. To compare the stats he netted 158 times for Liverpool over eight seasons, compared to only 60 occasions in the next seven.
I won't delve too deep into the reasons why El Nino should have stayed at Liverpool. Instead I will just provide the goal to games percentages from each of the sides he has played for.
This will allow anyone to make up their own minds as to why he should not have bailed just because the going was getting tough at Anfield. If only he knew what was to happen under Dalglish right?!
Atletico Madrid: 38.32 percent of games scored in.
Liverpool: 63.75 percent of games scored in.
Chelsea: 5.88 percent of games scored in.
You don't win PFA player of the year for nothing. Raul Meireles was probably Kenny Dalglish's biggest turnaround.
After an uninspired start to his Liverpool career under Roy Hodgson, he materialised into a machine when Dalglish took over. It's hard to believe he only scored five goals for Liverpool before his late dramatic switch to Stamford Bridge yesterday.
His stay was short and brief, but it was remarkable and outstanding. Whilst the likes of Charlie Adam and Jordan Henderson will console Liverpool fans as worthy replacements, there is still a feeling of disbelief at his untimely exit.
Whilst you can respect his decision to reunite with a former boss, it will truly be a case of hindsight prevailing depending on who finishes higher in the league come May.
Only then shall we see if Liverpool can indeed beat Chelsea without the second player within 12 months they have lost to them.
When you possess a player capable of breaking another footballers legs just with the ferocious fire power behind his shots, it's hard to imagine why you would let go.
Alan Smith will remember that incident with a lot of painful flashbacks but even he would question the decision of Liverpool to ship Riise off to Roma.
Fabio Aurelio seemed to take Riise's favoured position during the 2007/08 campaign and the Norwegian's exit was all but confirmed after his infamous own goal against Chelsea in the semifinal of the Champions League.
If you ask most Liverpool fans who was better—Aurelio or Riise—most will pluck for team ginger. He was a player who scored numerous beautiful goals in a Liverpool shirt, whilst also encompassing an attacking style that broke many conventions as to what was required from a left back.
A switch to Roma was slightly successful before Riise returned to the Premiership to play for Fulham. It remains to be seen how he will fair with the Cottagers. As their most celebrated signing of the summer, if the team fails to deliver, it won't be long before he moves on.
Liverpool however should have never given him that option.
Alright, so there was little Liverpool could do to keep hold of Mascherano. Yet his final performance and consequential standing ovation showed how much the side would miss such an influential Argentinian.
He created opportunities and his hard grafting playing style gained attention from the world over. Many feared playing against him due to his lack of inhibitions about how to win the ball. Sometimes it got him into hot water, but that was a downside Liverpool fans accepted due to his magnificent talent.
His Champions League win with Barcelona is well deserved for a player who missed Liverpool's own European triumph just a couple of years before his transfer to Anfield.
Another player who moved onto bigger and better things and therefore someone who was a lost cause to hold on to was former Liverpool hero Xabi Alonso.
Alonso brought a skillful aspect to the side not seen under Houllier as new boss Rafa Benitez attempted to approach the squad with a talent over strength policy.
This approach paid off when Alonso aided the team in their Champions League triumph of 2005. His appearance in the second half against AC Milan was regarded as one of the deciding factors to the teams dramatic come back.
His passing style and at times inspired strikes from a distance furthermore gained his reputation as a world class star.
As Liverpool completed following seasons without further silverware however, it was only a matter of time before Alonso put his career as a main priority.
Check out his goal in the compilation clip—where he scores a goal from his own half against Newcastle United, thus creating a Premier League record.
Although Robbie Fowler was never going to last in his second spell at Anfield, it was his first period from 1993 through to 2001 that created a Liverpool legend.
Some may argue that his best years were already behind him when he left for Leeds United in 2001. He struggled to keep injury free in his last few seasons at Liverpool but still netted 17 goals from 27 games in the 2000/01 campaign.
In essence, he was regarded as one of the games most prolific and natural of goal scorers. He did after all net more than 30 goals in two league campaigns—a feat rarely repeated by any player.
If he had stayed at Anfield, alongside Michael Owen, they could still have provided the most impressive all English strike force in the Premiership. It was a partnership we did not see enough of, but when we did it was sensational.
His spells at Leeds and then Manchester City were fulfilling but not amazing so his shock return to Liverpool in 2005 was reacted to with a great wave of optimism.
He found the net 12 times in 30 starts and put behind him the days of line sniffing celebrations and Graeme Le Saux. He completed a controversial career with spells at Cardiff and Blackburn before moves to Australia and now Thailand.
But it is those lost years between 2001 and 2005 that we may always wonder, what would have been?