Tottenham will hope the £40million signing of James Maddison can end a dismal run of expensive mistakes in the transfer window.
But there is one player they almost signed for a similar fee who would have guaranteed success.
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In January 2022, Colombia and Porto star Luis Diaz was on the market for around £40m.
With 14 goals in 18 Primeira Liga matches, the winger was beginning to attract interest from top clubs across Europe.
Diaz still had more than two years left on his contract – but a £66m release clause meant he was available.
Tottenham were willing to pay £46m and their opening bid of £37.6m was rejected by the Portuguese club.
Spurs only had three days left of the winter window to complete the deal – and Liverpool read the urgency of the situation.
The Reds were long-term admirers of Diaz and manager Jurgen Klopp had already identified the forward as his top summer target.
While Tottenham dragged their heels, Liverpool acted quickly and decisively.
The Reds hijacked the move by offering a deal which could reach £50m, including an up-front fee of £37.5m plus a further £12.5m in potential bonuses.
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Spurs were adamant that Diaz’s desire to join Liverpool meant there was nothing that could be done.
The Reds did not financially outmuscle their rivals and the total value of the bids were similar.
However, the Colombian’s father told a slightly different story about how his son ended up joining Liverpool instead of Tottenham.
“Tottenham was one. Roma was also left behind in the process. They hesitated a lot and let themselves be caught by Liverpool,” Diaz Sr said to BluRadio’s Blog Deportivo in February 2022.
“Liverpool were faster than them, they needed him and they took him away.
“There were many suitors who wanted Luis’ services, but he had the dream of reaching Liverpool. Because Liverpool are an elite team.
“After the first game, he told me that it was a team that works hard, complete, in which he will feel comfortable and will have the chance to play with high-performance players.”
Diaz rubbed salt into Tottenham’s wounds with an electric start to life at Anfield.
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The 26-year-old injected incredible energy into Klopp’s side and adapted to the Premier League instantly.
In the 13 remaining matches of the 2021/22 season, Diaz registered four goals and three assists, starring in a run that saw Liverpool win their last six games and miss out on the title by one point.
Injury plagued the 2022/23 season for Diaz, who featured for less than half of the campaign.
After the departure of Sadio Mane, Diaz was sorely missed as the Reds limped to a fifth-place finish.
But perhaps his absence was more acutely felt in north London, where Tottenham ended up finishing eighth.
In the summer of 2022, Spurs used much of the Diaz money to sign Richarlison from Everton in a deal worth up to £60m.
The Brazilian only managed one goal in the Premier League in his debut season at Spurs.
Fast-forward a year and Tottenham acted quickly to win the race for Maddison this summer, fending off Newcastle and getting the deal done early.
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Like many of Liverpool’s transfer dealings, there was little fuss and the deal was announced without a drawn-out saga.
Maybe Spurs chief Daniel Levy is finally learning from past experiences.
