Michael Olise one of 13 brilliant players Chelsea missed out on – & who they signed instead

 Credit: Alamy
Credit: Alamy

With Chelsea’s vast spending power over past 20 years, one might think they’d be capable of securing all of their targets. That, however, could not be further from the truth.

There have been plenty of times that Chelsea have gone for top players, but those players, for whatever reason, have chosen to stay put or go elsewhere.

Michael Olise is just the latest target that the Blues have pursued publically only to miss out – the 21-year-old winger has rebuffed their interest and signed a new, extended contract at Selhurst Park. It remains to be seen whether Chelsea signed someone else, but sometimes bagging alternative targets haven’t worked out too badly.

We’ve taken a look back at some of the biggest names who nearly ended up at Stamford Bridge… and who ended up there in their stead.

Sergio Aguero

Back in 2009, having ceded three straight Premier League titles to Manchester United, Chelsea needed to refresh their frontline.

Sergio Aguero was one of their main targets after the striker helped Atletico Madrid to Europa League glory, and a fee was even agreed upon for the 21-year-old.

However, after Aguero’s wage demands didn’t match with what Chelsea wanted to pay, the Argentine stayed in Madrid for two more years before moving to Manchester City in 2011.

Ironically, Chelsea’s one attacking signing that summer came from City, with Daniel Sturridge arriving on the cheap.


City had got one over on Chelsea in 2008, too, signing Robinho following their cash injection after it had looked for much of the summer as though the Brazilian was on his way to Stamford Bridge.

Real Madrid had seemingly named their price, and the Blues were thought to have prioritised the Brazilian after former Selecao head coach Luiz Felipe Scolari replaced Avram Grant in the dugout.

It would end up being a quiet deadline day for the club, though, and the closest they got to an attacking recruit was the January loan of Ricardo Quaresma, who hardly set Stamford Bridge alight.

Dani Alves

If you’re wondering how close Alves was to moving to Chelsea, we even reached the “will become their player today” stage of the newspaper discourse.

The move was thought to be hours away in 2007, when the Brazilian was ready to leave Sevilla and had seemingly chosen the Blues ahead of Real Madrid, only for Barcelona to swoop in at the last minute.

Perhaps Jose Mourinho would have been able to stick around longer if he’d secured the right-back he wanted, rather than the backup option of Juliano Belletti.

Mehdi Benatia

Chelsea were actually linked with Benatia twice – once in 2014, when he ended up leaving Roma for Bayern Munich, and once a decade earlier.

“They were a great team, but I did not feel ready to go,” the Moroccan later said of his three-day trial as a teenager, during which time he was living with Didier Drogba and Claude Makelele.

Chelsea did sign another teenage centre-back around the same time, Santos youngster Alcides, but the Brazilian was unable to break into the first team and left in 2008 without playing a minute for the club.

Roberto Carlos

The same summer that Chelsea almost signed Dani Alves, they came close to signing another Brazilian full-back – can you imagine the sight of the young pretender on one side of the pitch and the old hand on the other?

“I spoke to Roman Abramovich about it. We had a meeting in Paris, but it didn’t happen due to a few small factors,” Roberto Carlos would reveal 10 years after the nearly-deal of 2007.

Instead of a two left-back system with Ashley Cole, Chelsea instead signed an orthodox left-winger in Florent Malouda, leaving the Brazilian free to join Fenerbahce from Real Madrid instead.

Roberto Carlos did end up playing for an English club in 2022, though…

Roberto Carlos (centre) poses for photographs with Bull In The Barne United players at the Hanwood Village Hall Recreation Centre, Shrewsbury. Friday March 4, 2022. Credit: Alamy
Roberto Carlos (centre) poses for photographs with Bull In The Barne United players at the Hanwood Village Hall Recreation Centre, Shrewsbury. Friday March 4, 2022. Credit: Alamy

READ: I saw Roberto Carlos play Sunday league… and it was gloriously sh*t

Steven Gerrard

Chelsea were keen on Gerrard for much of the 2004-05 season, to the point that the England midfielder went as far as handing in a transfer request in an effort to force through a move shortly after Liverpool’s Champions League victory.

Jose Mourinho was a known admirer of the midfielder, but the impasse between Liverpool and their player would eventually come to an end when he decided to stay and sign a new deal, remaining at Anfield for a further decade.

With a move for Gerrard off the table, Mourinho had to look elsewhere, and that meant a £24million move for Lyon’s Michael Essien. That one seemed to turn out okay in the end.

Liverpool's Steven Gerrard and Chelsea's Frank Lampard Credit: Alamy
Liverpool's Steven Gerrard and Chelsea's Frank Lampard Credit: Alamy

READ: Seven star names who didn’t get their big move away: Gerrard, Rooney…

Edin Dzeko

When Chelsea signed Emerson in January 2018, he wasn’t the only Roma player the club wanted to bring in.

Dzeko was unable to agree personal terms, however, and we can certainly take at least one positive from the breakdown of the deal – had it gone through, we’d have missed out on the Bosnian’s starring role in Roma’s sensational comeback against Barcelona in the Champions League quarter-finals.

Chelsea ended up turning to Olivier Giroud, who scored 40 goals for the club and left with Champions League, Europa League and FA Cup winners’ medals. Not too shabby.

Andrea Pirlo

The 2009-10 season – when the Blues won the Premier League and FA Cup Double – could have been even more successful if all of the club’s transfer targets had arrived.

Carlo Ancelotti wanted to bring Andrea Pirlo over from Italy, and – as Pirlo would later recall – it could well have happened if AC Milan hadn’t already lost Kaka that summer.

Chelsea only signed one central midfielder that summer, Nemanja Matic joining from Kosice for his first Chelsea stint, and John Obi Mikel was the closest the club had to someone in the Pirlo role that year.

Franck Ribery

Another nearly-man from the 2009-10 season, Ribery was linked with a big-money move to Carlo Ancelotti’s side, and Uli Hoeness claimed a bid of €65million plus Jose Bosingwa was turned down.

Ribery may have found himself wondering what might have been. Bayern endured a difficult start to the season under Louis van Gaal (they were down in seventh in October) and he missed most of the first half of the season through injury.

However, his return coincided with a title charge and a run to the 2010 Champions League final.

The Frenchman would eventually end up playing under Ancelotti, but it would need the Italian to come to him in the form of a year and a bit in Bavaria.

Chelsea, meanwhile, had to make do with Yuri Zhirkov. Still, with Ribery on their books, perhaps there would have been no room for Eden Hazard three years later. 


In the summer of 2007, after the humiliation of needing to give Manchester United’s fringe players a guard of honour at Stamford Bridge, Roman Abramovich was intent on reclaiming the title.

One of his main targets was Ronaldinho, with the Brazilian’s previous performances against Chelsea clearly living long in the memory. But Barcelona were not in a selling mood.

The Blues brought in Florent Malouda that summer but decided to dip back into the transfer market in January to secure Nicolas Anelka for £15million from Bolton.

Ultimately, despite going unbeaten from December 23 until the end of the season, they didn’t have enough to deny United back-to-back titles.

Ronaldinho might not have made the difference, though, as injuries limited him to just 26 games in all competitions that season.

David Silva

When Chelsea looked to launch their title defence in 2010, their squad arguably didn’t need a great deal of strengthening. One man who would have certainly improved them, though, was Silva, then still at Valencia.

“There is no doubt in my mind that Chelsea would be a great club to play for – and a club where I could fulfil my ambition of league titles and the European Cup,” the Spaniard was quoted as saying at the time.

But he would ultimately choose Manchester City as his Premier League destination – a move which he’s probably pretty happy to have made.

The Blues instead signed a different creative midfielder with plenty of flair and quick feet, but it’s fair to say Yossi Benayoun didn’t quite have the same impact.


The Athletic’s transfer specialist David Ornstein revealed that back in 2018, Chelsea had a chance to sign Alisson, who had established himself as Brazil’s No.1 and was coming off the back of an exceptional season with Roma.

However, they “hesitated” in the hope Thibaut Courtois would stay, but he still ended up at Real Madrid, and by that point Liverpool had moved ahead of them in the race to sign Alisson with a world-record fee for a goalkeeper.

Chelsea beat it just a few days later when they signed Kepa Arrizabalaga, highly rated at Athletic Bilbao at the time.

Kepa has struggled – to the extent that Chelsea replaced him with Edouard Mendy – while Alisson has put himself in the conversation for best in the world for his hand in Liverpool’s Champions League win and Premier League title.

Still, Kepa has ended up rocking up at the Bernabeu on a season-long loan after Courtois’ serious injury. Funny old world, isn’t it?

READ MORE: Dirty Secrets: I’m not a Chelsea fan, but I’ve always quite liked them

TRY A QUIZ: Can you name Mourinho’s 35 most-used players throughout his career?

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