From Willian to Eden Hazard, Tottenham supporters know the pain of seeing some top players choose to go to Chelsea over their club – but it’s not always one-way traffic – as the imminent signing of Xavi Simons demonstrates.
Simons was of strong interest to Chelsea earlier in the summer of 2025, but Tottenham swooped in at the last minute to convince the Netherlands international to move to north London instead.
Alongside Simons, we’ve identified five other players who reportedly chose Spurs over Chelsea.
Xavi Simons
We doubt Tottenham technical director Johan Lange reads our work here at Planet Football, but we want a consultancy fee if he does.
“Twelve years after the Willian hijacking… wouldn’t it feel extra sweet to get one over the Blues?”
That’s the question we asked when we stuck Simons’ name on the shortlist of potential James Maddison replacements. Well, Spurs fans – how does it feel?
At the time, Chelsea appeared in pole position to sign the talented Dutch playmaker from RB Leipzig.
But we suggested that Spurs should try to hijack the deal by offering him a more clearly-defined role in the starting XI. And so it’s proven the case.
He’s completed a medical and the clubs have agreed on a fee.
Given what happened with Willian, we understand any Tottenham supporters who won’t believe it until an official announcement – but it sounds like this one is done and dusted. Surely.
Danny Rose
“I started at Leeds when I was 11. I came to Tottenham at 16. When I joined Leeds I was pretty raw,” Rose reminisced on his early years in an interview with Instagram channel don.emusic.
“I didn’t know about one-touch passing. It took me a couple of years to get to grips with everything and by the time I was 14 I was one of the best.
“I could have gone to Chelsea when I was 15, I went to the training ground but I didn’t fancy it and I chose Tottenham the year after.
“It was pretty daunting, I was nervous, I needed it. You know what 15-year-olds do when they are around their mates all the time. I needed to get away and I am glad I did.”
That choice worked out alright for Spurs. After announcing himself with that unforgettable screamer in the North London Derby, he made over 200 appearances for the club and for a time was one of the best left-backs in the country.
Steven Pienaar
The South Africa international joined Spurs in a £3million deal back in January 2011, but Chelsea reportedly also agreed a fee with Everton. The choice was ultimately down to the player.
“It wasn’t about the money, it was about ambition,” Pienaar told The Guardian.
“We want to fight and to play every game at the highest level and play in the Champions League and that’s what I want every season, and that’s why I made the decision to join Spurs.
“The decision I made may not be the right one, but I followed my heart and prayed for the answer. Joining Tottenham was the answer.
“I asked a lot of people and some said go to Chelsea, some said go to Spain, some said go to Tottenham. Some may not like it but this is my decision. If I fail then it’s my responsibility.”
Unfortunately it didn’t really work out for Pienaar in North London, and after making only a handful of appearances in half a season, he returned to Everton.
Brennan Johnson
Chelsea were reportedly one of the leading clubs in the race for Johnson’s signature back in the summer of 2023.
That makes sense, given that they were still seemingly targeting every young wide attacker on the market in those early Todd Boehly years.
They lost out on Crystal Palace’s Michael Olise and ended up bolstering their attack with Christopher Nkunku, Nicolas Jackson and Cole Palmer during that window.
The Daily Mail claimed that Johnson preferred Spurs “over a bloated Chelsea side in order to get more game time.”
Mohammed Kudus
According to The Sun, Chelsea offered Kiernan Dewsbury-Hall plus a further £20million to sign the exciting Ghanaian dribble king from West Ham.
Kudus was high on the Blues’ list of targets, while the player was open to a move to Stamford Bridge – even going as far as agreeing personal terms.
Ultimately, Tottenham’s swift and decisive approach won out. Who knows how things might’ve turned out had they taken the same tack with Morgan Gibbs-White or James Maddison?
James Maddison
Chelsea spent somewhere in the region of £1billion over the course of Boehly’s first year at the helm and Leicester City playmaker James Maddison had frequently been cited as a top target in their potential rebuild.
Many reports suggested that Chelsea opted against Maddison due to their youth-focused recruitment strategy. They ended up signing 21-year-old Cole Palmer instead.
But that’s reportedly not entirely true. Maddison’s heart being set on Spurs was also a factor.
“Chelsea’s strategy has been to largely look at players 25 years old and under,” transfer reporter Ben Jacobs told Caught Offside.
“And it’s true they passed up on going for James Maddison, who is now 26. But that wasn’t really down to age alone.
“There will always be exceptions to the age ‘rule’. After all, Mauricio Pochettino is also very keen on having Premier League experience. That’s why Raheem Sterling is seen as so important this season.
“Chelsea looked at lots of targets, which is normal in a busy window. But they also knew Maddison preferred the move to Spurs.”
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