Every football team has more than a handful of players they were once linked with but never quite managed to sign. At Arsenal, for instance, Arsene Wenger had hoped to sign Cristiano Ronaldo. Manchester United were linked with Ronaldinho the same summer, and ended up getting the Portuguese star instead.
As one of the biggest Premier League clubs, Liverpool also have a few big names who fall into this category. Interestingly enough, current Tottenham Hotspur midfielder James Maddison fits the bill on that front.
Speaking on a 2025 episode of the Libero podcast, respected English football journalist Rory Smith revealed how close the Spurs star came to joining the Reds as a teenager, but his actions actually scuppered a deal.
Rory Smith Leaked Transfer Interest in James Maddison
'Liverpool got annoyed'
Smith recalled how Maddison was a target for Liverpool when he was still playing for Coventry City as a 19-year-old. After he leaked a story on the potential transfer, however, the deal abruptly came to an end. He explained:
"I once stopped James Maddison signing for Liverpool. So getting stories can genuinely have an impact.
"They were looking at him when he was at Coventry [City] and they made a bid and I happened to be speaking to a friend of mine who was running Coventry at the time who mentioned that they'd had this offer from Liverpool for James Maddison, this 19-year-old who I think at that stage everyone thought was going to be really good but he wasn't a superstar.
"And basically Liverpool, when it got kind of leaked into the public domain, I was told years later, Liverpool got annoyed because they thought that Coventry were trying to do it to smoke out interest."
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In the end, Maddison signed instead for Norwich City – although then spent the remained of the 2015/16 season back on loan with the Sky Blues. He'd go on to spend a season on loan at Aberdeen in Scotland before eventually making his way to the Premier League.
James Maddison's Career Stats
Club
Leicester
Tottenham
Norwich
Coventry
Aberdeen
Maddison Ended up at Leicester City
Would later join Tottenham Hotspur
Maddison would not join Liverpool in the English top-flight, though, but instead end up playing for Leicester City. To make things worse, he even managed to upset iconic Reds manager Jurgen Klopp during his time with the Foxes.
Indeed, the German once admitted he 'doesn't like' Maddison after the midfielder failed to close down Vincent Kompany during his time at Leicester. The Manchester City captain was allowed the space to score a screamer, which wrecked Liverpool's title chances in 2019.
"The moment when Vincent Kompany touched the ball there, I am really happy I didn't get a stroke in that moment as that's how it must feel," Klopp recalled.
"I remember exactly how I was lying on the sofa watching and thinking 'Maddison block him, close him down.
"Since then I don't like Maddison. I was angry with Brendan [Rodgers] that day because he should have taken him off, he was tired.
"Leicester played really good first half, after that they should have scored.
'It's just a personal thing, I have no problem with him, but when I see him it's... and now I saw him again last weekend."
Maddison's time at Leicester would be a largely positive experience, though, as he lifted to FA Cup in 2021, although it ended in disappointment with the Foxes relegated shortly before his exit in 2023. That summer, he was linked with a number of Premier League clubs, including Liverpool, but he'd sign for Spurs instead.
The Englishman would arrive in North London for a reported £40 million and remains a key player for Spurs now, having helped the club end their trophy drought in 2025 – although he was injured so couldn't play in the Europa League final win over Manchester United.
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Stats via Transfermarkt - correct as of 23/06/25