Liverpool boss Jurgen Klopp once described missing out on signing a Tottenham star as the 'biggest mistake of my life'.
Klopp has been at Liverpool since 2015, where he has completed transfers for some of football's top players.
One of his major legacies at the Reds, though, is signing high-quality players and making them even better - showcased by the likes of Mohamed Salah, Sadio Mane and, more recently, Dominik Szoboszlai.
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But he has missed out on a number of players too. One of those was Aurelien Tchouameni, with the former Monaco midfielder admitting he turned down Liverpool before joining Real Madrid last year.
This summer, they had a British-record transfer fee accepted for Moises Caicedo, but the Brighton midfielder demanded to join Chelsea instead.
Klopp's player development strategy is similar to the one he used at Dortmund, with the likes of Ilkay Gundogan, Pierre-Emerick Aubameyang and Marco Reus among those to star in the Bundesliga.
His early years at the club effectively saw him take a group of previously 'unfancied' players and develop them to become German champions.
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But one player he was desperate to sign was Son Heung-min, who played in the Bundesliga with Hamburg and Bayer Leverkusen before sealing a 2015 move to Spurs.
The South Korea international is one of Spurs' finest players of the Premier League era, but he turned down the chance to join Dortmund in 2013.
Recalling the failed transfer in 2021, Klopp explained to Korean outlet KBS News: "One of the biggest mistakes in my life is not signing Son Heung-min.
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"Outstanding player. He is fantastic, a sign of Korean football and one of the best strikers in the world."
Explaining why he turned down Klopp, Son said: "I wanted to stay in the Bundesliga. Leverkusen and Dortmund wanted me.
"Both teams play in the Champions League but I thought Dortmund would use rotation more than Leverkusen. That's why I joined Leverkusen."
Spurs host Liverpool at Anfield this evening - and Klopp will hope Son doesn't prove to be the difference maker.
Topics: Liverpool, Borussia Dortmund, Tottenham Hotspur, Premier League