‘Arsene Wenger almost signed him’ may be a running joke in north London, but Tottenham Hotspur also have their fair share of transfer near-misses.
Indeed, the two biggest stories of the January transfer window at Spurs weren’t the arrivals of Dejan Kulusevski and Rodrigo Bentancur, they were the failed pursuits of Luis Diaz and Adama Traore.
Diaz and Traore certainly aren’t the only two players Spurs have tried and failed to sign in recent years, and with that in mind, we’re going to look at an XI of players Tottenham could have signed.
GK: Gianluigi Donnarumma
Gianluigi Donnarumma broke England fans’ hearts in the summer with his penalty shootout heroics in the Euro 2020 final, and he very nearly joined Spurs in wake of that tournament.
Indeed, Donnarumma came into this summer as a free agent, and Fabio Paratici made an attempt to bring him to Spurs when his contract expired at AC Milan.
Sadly for Tottenham, he decided to join PSG.
RB: Max Aarons
Norwich City star Max Aarons is now being linked with Arsenal, but once upon a time, he was a concrete target for Tottenham.
Unfortunately, Jose Mourinho vetoed the move due to the fact he though Aarons was too small. Matt Doherty and Emerson Royal have since been signed to play at right-back, but neither player has covered themselves in too much glory since joining Spurs.
CB: Virgil van Dijk
This one has to hurt.
According to The Athletic, back in 2015, Spurs were torn between signing Toby Alderweireld and Virgil van Dijk – then at Celtic, and they opted to go for the Belgian.
Alderweireld was a fantastic servant for Spurs, but it has to be said that van Dijk would have been even better.
CB: Mateo Musacchio
From one that Spurs probably regret to a lucky escape.
Tottenham tried to sign Mateo Musacchio back in 2017, with his agent claiming that the Argentine knocked back two approaches.
“In 2017 we said no twice to Tottenham, and in 30 seconds we said yes to Milan,” his agent said.
Since then though, Musacchio’s career has been on a downward spiral, and he’s currently without a club at the age of 31.
LB: Kieran Tierney
Tottenham scouted Kieran Tierney extensively back in 2017, but just one year later, he was making a move to Arsenal.
The Scot is now a bona fide star for the Gunners, but he could have been a key player for Spurs in another lifetime.
CM: Bruno Fernandes
Admittedly, our midfield isn’t the most balanced, but there are so many quality attacking midfielders Spurs have almost signed.
Bruno Fernandes is perhaps the biggest name in the midfield, and he’s gone on the record to speak about how close he came to joining Spurs.
“I was close to Tottenham. In the summer I was closer to Tottenham than Manchester,” he told the Official Manchester United Podcast.
“Sporting thought at that moment the proposal was not good enough, they thought they deserved more for a player like me. They wanted more money. I was not mad, I was sad.”
Fernandes is now one of the highest-paid and most talented players in the Premier League.
AM: Paulo Dybala
Paulo Dybala almost joined Tottenham in 2019, but an issue with his image rights saw the deal collapse at the last minute.
Dybala is going to be leaving Juventus on a free transfer this summer, so perhaps Spurs could go back in for the Argentine.
CM: Emile Smith Rowe
The second Arsenal star in this team, Emile Smith Rowe was a player Tottenham looked at when he was just 16.
David Webb told the What The Footie Podcast just how close Smith Rowe came to joining Spurs.
“A good example is Emile Smith Rowe, we got him on loan when we were at Huddersfield from Arsenal. He was a player I knew all about from when he was quite young. We tried to take him at Tottenham when he was 16 or 17,” Webb said.
“We followed his path when he went to RB Leipzig, and when you look at a talent like that he was coming into a completely different environment, it was a needs must at the time as Huddersfield needed a player in that sort of position,” Webb said.
RW: Willian
Perhaps one of the most famous transfer sagas of the Premier League era, Willian had all-but signed with Tottenham before deciding to join Chelsea in 2013.
Willian claims that he was at Spurs’ training ground for eight hours before eventually heading to Stamford Bridge to finalise a move to the Blues.
LW: Jack Grealish
This is another painful one.
Jack Grealish is England’s first £100m player, but Spurs could have had him for a fraction of the price.
Grealish even waved goodbye to the Aston Villa fans after a game against Hull believing that he was Spurs-bound, but he decided to stay loyal to the Midlands club after their financial difficulties subsided.
“At Hull, I was 95 per cent sure it was going to be my last game. I waved to the fans when I got taken off as I thought I was going. Even on the Thursday morning of the transfer window, I thought I was leaving,” Grealish said.
“Before the new owners [arrived], Villa needed the money so I kind of accepted that me going would save the club. I think the fans would have taken that, too, because we needed the money.
ST: Pierre-Emerick Aubameyang
The last player in this XI is another with strong ties to Arsenal. Pierre-Emerick Aubameyang admitted last year that he almost joined Spurs.
“I was close to signing for Tottenham,” Aubameyang told Sky Sports.
“It was when I was at Saint-Etienne. I came here I went to the stadium as well at White Hart Lane, but the day later they never called back, so I was like ‘ok, no worries’,” Aubameyang said.
Since that failed move, Aubameyang has proven himself to be one of the best strikers on the planet, and he’s even won a Premier League Golden Boot.
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