Liverpool have become accustomed to losing out to Real Madrid in recent years but only one player has added insult to injury at Anfield.
The Reds will look to snap their horror run against the Champions League winners, live on talkSPORT, amid a host of potential what-ifs.
Liverpool have drawn once and lost seven of their last eight meetings with Los Blancos, which included two European final defeats.
The Merseysiders have also been gazumped by the Spanish giants at nearly every turn in the transfer market during this period.
In an alternate timeline, Kylian Mbappe, Jude Bellingham, Aurelien Tchouameni, and Rodrygo could have all been playing for Liverpool.
To add further insult to injury, Madrid are now keen on signing the club’s vice-captain and academy superstar Trent Alexander-Arnold.
Alexander-Arnold, who is close friends with Bellingham, is out of contract at the end of the season and is yet to agree a new deal.
Interest from Madrid will undoubtedly ramp up for their trip to Liverpool in the Champions League on Wednesday.
Unfortunately for Liverpool, the 15-time winners are no strangers to finalising agreements for players near Anfield.
Rodrygo, who won’t make the flight to England due to injury, was highly coveted by Jurgen Klopp.
During the German’s first full season in charge of the Reds, he had tried to sign the 23-year-old when he was only a teenager.
Rodrygo was still plying his trade in his Brazilian homeland and Klopp flew to Sao Paulo personally to monitor his development.
His agent, Nick Arcuri, explained to Canal do Nicola in 2020: “When Rodrygo went to sign his first professional contract with Santos, aged 16, a Liverpool director called me saying that Klopp already knew the player, had seen the material, had already come to see Rodrygo personally.
“He had gone on YouTube, searched ‘talents from Brazil’, Rodrygo had appeared and he was very young.
“He came to Brazil and liked him. They contacted me, the Liverpool director wanted him to be his first signing, Rodrygo.”
Former Manchester City midfielder Elano was working at Santos in early 2017 when he got wind of Liverpool’s cut-price deal.
“I went to the board and said, ‘No, no, we can’t let him leave for this,’” He told BBC Sport.
“It was a 3m euro offer only and the talks were already at an advanced stage. It was pretty much a done deal. They had a verbal agreement but I insisted, ‘We can’t do this’.
“He was just 16 years old back then and, although the team had high hopes for him, it was not clear yet when he would be playing for the senior side. So I went to Rodrygo and told him, ‘We will promote you soon. You have my word.’
“A little while after, I ended up taking charge as a caretaker manager and so, much sooner than expected, I could do what I had promised him.
“I brought him to train with us and gave him his first minutes as a professional footballer.”
Rodrygo ultimately spent another season at Santos but a year later he was at Anfield signing for his new club… only it wasn’t Liverpool!
Most of the Kop had eyes on Alisson Becker, and former Red pair Roberto Firmino and Philippe Coutinho when Brazil beat Croatia 2-0 at Anfield in a World Cup warm-up match in June 2018.
Yet just metres away from the pitch in a box at Liverpool’s historic ground, Rodrygo was finalising a move to Madrid.
On the eve of the game, Santos’ then president Jose Carlos Peres met Real sporting director Juni Calafat in a cafe next to Brazil’s team hotel in Liverpool.
“Our talk didn’t last more than 30 minutes. They had come to Liverpool to close a deal and were not willing to leave the table without one,” Peres told Bleacher Report.
Rodrygo has enjoyed a gluttony of success since arriving at the Santiago Bernabeu, winning the Champions League twice.
His greatest individual highlight remains his dramatic two late goals to complete a semi-final comeback win over Manchester City in 2022 en route to Madrid’s 1-0 triumph against Liverpool a month later.
However, the arrival of Mbappe this season has relegated him to the periphery of Carlo Ancelotti’s thinking.
Explaining his decision to reject Liverpool earlier this year, Rodrygo said: “We didn’t close the deal because I didn’t want to. I wanted to stay at Santos even though the offer was very good.
“The pathway they promised me would also have been very good for my career. I was going to finish my studies in England to prepare for European football. It had always been my dream to play in Europe.
“Everything was very good, but my desire spoke louder. I wanted to stay at Santos and make a bit of history at the club. And that’s what happened: I was able to fulfil my dream of playing for Santos. But it’s true, I almost went to Liverpool.”
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