Football clubs are littered with 'what if' transfers and none of them come much bigger than Liverpool.
Stephen Pickering takes a blast through the past to have a look at seven transfers that will leave the Anfield faithful with their heads in their hands.
7): Simao Sabrosa - In 2005 Liverpool were reportedly very close to signing Simao Sabrosa, usually known as just 'Simao'. The former Barcelona winger has enjoyed a fruitful career in football, spending time at Europe's biggest clubs. He made over 85 appearances for Portugal and in the height of his career was close to moving to Liverpool for £10 million. He flew out to England to undertake a medical, but unfortunately the deal fell through and Simao never got to play in the Premier League.
6): Nicolas Anelka - in 2002, Gerard Houllier turned down the chance to take up an option to buy for the well traveled French international. Anelka has won major competitions all over the world, including the Champions League and built up a fine reputation. The French manager later voiced his regret on the decision, admitting it wasn't down to his quality but his agents.
5): Mario Gomez - in 2012, Jamie Carragher lifted the lid on Liverpool wanting to sign Mario Gomez but subsequently ending up with Andy Carroll. It's safe to say that Andy Carroll's days at Liverpool always had huge potential to become a massive flop and did. Mario Gomez on the other hand went on to net 28 goals the year after Liverpool pursued him and has won numerous trophies in Germany with Bayern Munich.
4): Mario Gotze - in 2011, Liverpool reportedly had the choice between signing German starlet Mario Gotze or England starlet Jordan Henderson. Both Dalglish and Damien Comolli said Jordan Henderson was their number one target. They unfortunately landed their man and despite coming to form recently, it must still stick in the teeth of some Liverpool fans.
3): Dani Alves - in 2006, Liverpool managed to entice a figure out of Sevilla for their highly rated young full-back Daniel Alves. The board on the other hand, thought the asking price of £8 million was too high and decided to look elsewhere. A couple years later the full-back moved to Barcelona for a figure around £30 million pound and became known as one of the best full-backs of this generation... ouch.
2): Nemanja Vidic - in 2006 Daniel Alves was not Liverpool's only mistake. During an interview with FourFourTwo the Manchester United legend admitted to holding talks with Liverpool before his move to Manchester United in 2006. The defender claimed the meetings just stopped with Liverpool, and in the end the move to Manchester United was the correct choice.
1): Cristiano Ronaldo - in 2003 Ronaldo signed for Manchester United, however, according to Gerard Houllier things could have been very different if he would have been given the green light to sign him. The French manager admitted to watching Ronaldo on plenty of occasions, but unfortunately at the time Liverpool couldn't meet the asking price or the wage for the talented winger. I think it's fair to say this was their biggest mistake, and with Ronaldo could have changed the shape of their history.
image: © Jan Solo