They were the deals Liverpool should have done.
But somehow didn’t.
The transfers the Reds fancied, thought about and sometimes even tried to pull off – only to find themselves facing disappointment.
But which ones are the most disappointing of all?
Six of our writers have had their say on the worst (or should that be best?) transfer near misses in Liverpool history.
Paul Gorst: When Liverpool lost their hard-headed, South American firebrand in Luis Suarez in the summer of 2014, Alexis Sanchez appeared to be as close to a carbon copy as possible.
Instead, the hard-headed South American firebrand chose Arsenal instead. Reports suggested the the Chilean’s partner favoured London over Merseyside despite the Reds enjoying a much better Premier League season to the Gunners.
Sanchez would go on to flourish at Arsenal while the Reds were pressed into hurriedly signing Mario Balotelli.
The lack of a like-for-like for Suarez left Liverpool short and it was his exit that sparked the beginning of the end for Brendan Rodgers at Anfield. Even if that did come nearly 18 months later.
Theo Squires: Jurgen Klopp’s Liverpool might be littered with genuine World Class talent all over the pitch, but for most of my life-time that hasn’t been the case.
And that’s why the missed signing I rue the most is one of the original Galacticos, a Ballon d’Or winner and one of the true all-time greats.
Along with the likes of Zinedine Zidane, Ronaldo, and Pavel Nedved, he was one of those players you watched in awe every Champions League night in the late 90s and early 00s.
And after 10 years dominating La Liga with Barcelona and Real Madrid, Rafa Benitez very nearly brought the Portuguese genius to Anfield in 2005.
Sure he was the wrong side of 30 but this was Luis Figo and Liverpool were the newly-crowned European champions!
He could be Rafa’s Gary McAllister, providing that vital bit of experience and a born-winner mentality to take the Reds to the next level and end their drought to lift the Premier League.
Deemed surplus to requirements at the Bernabeu, he pleaded for a move to Anfield and a firm offer was on the table only for the Reds to haggle over the fee, wanting Figo for nothing rather than the reported £1m Real Madrid were asking for.
In stepped Inter Milan, making him feel more wanted to make the midfielder’s mind up.
Liverpool’s loss was Inter’s gain. Four years he spent at the San Siro, winning four Serie A titles before hanging up his boots with his quality continuing to shine through right until the very end.
Liverpool should have just stumped up the cash.
Sean Bradbury: Rafael Benitez’s side that was built in the years after Istanbul has to go down as one of Liverpool’s greatest ever ‘nearly teams’.
Peaking with a title challenge in 2009, that squad had almost everything.
Everyone remembers the ‘best midfield in the world’ starring Steven Gerrard, Xabi Alonso and Javier Mascherano.
Jamie Carragher and Pepe Reina were ever-present rocks at the back in the league, with plenty of capable allies across the defence.
And further forward, Fernando Torres and Dirk Kuyt helped provide the goals and the graft.
On the left flank much of the time, however, was Albert Riera. He played 40 games in all competitions over the course of the 08/09 campaign.
While a solid enough player, he lacked the star quality of virtually all his teammates. But there should have been another man in his place.
In 2005, not long after Champions League glory, the Reds made a move for talented Portuguese winger Simao Sabrosa.
As the ECHO wrote at the time, he “came within hours of a £10m move” to Anfield that summer. But Benfica’s president “blocked the transfer” as the player prepared to catch a flight to England.
Another report added: “Only a hostile reaction from Benfica fans prevented a deal going through, as board members in Lisbon feared a serious backlash after they had agreed the transfer.”
To make matters worse, Simao scored at Anfield just months later as his side dumped the Reds out of Europe in 2006. What could have been…
Connor Dunn: In 2006, Rafa Benitez spoke to Nemanja Vidic about bringing him to Liverpool from Spartak Moscow.
At 24, he was a centre-back for the future and an extremely promising one at that – as he showed when Manchester United swooped in and pinched the Serbian for just £7million.
The defender would have arrived just eight months after the Champions League triumph in 2005 as a long-term replacement for Sami Hyypia with the squad bolstered by the likes of Bolo Zenden, Momo Sissoko and Peter Crouch.
As it happened the Reds signed Daniel Agger in January before adding Martin Skrtel to the ranks with both very solid additions in the heart of defence but given what Vidic did at Old Trafford – minus his well-documented travails against Fernando Torres – he would have been a very serious signing to shore up Liverpool’s defence spectacularly for many years to come.
Dan Kay: Teddy Sheringham had already been a thorn in Liverpool’s side on numerous occasions for Nottingham Forest and Spurs before Roy Evans tried to bring him to Anfield in the summer of 1997.
After the previous two seasons’ near-misses in the FA Cup final and title race, the Reds boss was desperate to add more experience to his talented but brittle squad and lined up the Tottenham and England frontman along with French defender Marcel Desailly who was set to leave AC Milan.
But the club had a policy of not buying older players – despite later that summer bringing in 31-year-old Karl-Heinz Riedle from Borussia Dortmund – and Sheringham went to Manchester United, his inspirational role in the Old Trafford side’s Treble triumph two years later rubbing further salt in the wound.
Caoimhe O’Neill: Liverpool wanted him and almost had him, but Dani Alves was another one that got away.
That’s right. Once upon a time the right-back was on the cusp of finalising a transfer to Anfield from Sevilla but it unravelled at the last minute.
Reports suggest the Reds opted to spend the money on Dirk Kuyt instead. And I will have nothing said against the Dutchman, because I loved him. But my, oh my did Liverpool miss out on a Brazilian baller.
Alves instead moved to Barcelona and would go on to win it all. There’s no denying Barca was where the magic happened for the two-time Copa America winner. He won six La Liga trophies and three Champions League titles during his reign in Catalonia.
He even went on to enjoy spells with two more European giants in the shape of Juventus and Paris Saint-Germain. He is also the most decorated player in history having won 40+ trophies. Oh and talk about longevity he’s still plying his trade with Sao Paolo at the age of 36.
Liverpool sure could have done with his winning mentality on the flank, and there is no denying that it was a big mistake not getting that deal over the line.
Joe Rimmer: It felt like Liverpool were searching for the final piece of the jigsaw for most of my life.
First it was Roy Evans, then Gerard Houllier, Rafa Benitez had a go and then Brendan Rodgers.
None of them found it.
But there was a time when I truly believed Liverpool had identified the piece.
It was at Blackburn Rovers in the former of a strawberry blonde Irishman named Damien Duff.
He’d been outstanding at Anfield in a 4-3 defeat for Blackburn Rovers, scoring and terrorising Liverpool’s defence.
The Reds were heavily linked and, in dire need of width, it made perfect sense.
Duff was quick, great on the ball and had an eye for goal. He was one of the Premier League’s outstanding young talents and complimented what Houllier already had.
But Liverpool could simply never afford him and when Chelsea become the uber-rich club they now are in 2003, they blew the Reds out the water.
He’d win two league titles as part of an exciting front three at Stamford Bridge.