Picture this: Lionel Messi, draped in Chelsea blue, weaving his magic at Stamford Bridge. It sounds like a fan’s fantasy, but according to revelations from renowned transfer expert Gianluca Di Marzio, this came tantalizingly close to becoming reality back in 2014. This is the story of the greatest transfer that never was, a saga of secret talks, a charismatic manager’s pitch, and a dramatic family intervention that changed everything.
Jose Mourinho and Lionel Messi shared a respectful rivalry, a foundation that nearly led to a stunning partnership at Chelsea.
The Perfect Storm: Tax Troubles and Temptation
The year was 2014. Lionel Messi, at the peak of his powers with Barcelona, was facing a monumental off-pitch battle. A serious tax evasion probe launched by the Spanish government against his family had cast a dark cloud over his life in Spain. In his own words, it made him seriously consider leaving the country he had called home since he was a boy.
This vulnerability created a rare window of opportunity. While most saw an untouchable icon, visionary clubs saw a chance to pull off the unthinkable. As reported by Krikya sources, this period of uncertainty was the catalyst for what would become one of the most audacious transfer plots in football history. Chelsea, then under the command of the charismatic Jose Mourinho, were preparing to make their move.

The London Charm Offensive
The appeal of London and the immense respect Messi held for Jose Mourinho were the two pillars of Chelsea’s approach. The initial contact wasn’t made through official channels but through a friend—former teammate Deco. Having recently retired after a two-year stint at Chelsea, Deco acted as a bridge, promising Messi he would set up a meeting with owner Roman Abramovich.
The plot quickly advanced to a clandestine lunch at Mourinho’s London mansion. With intermediaries presenting the feasibility of the deal, a still-skeptical Mourinho decided to go straight to the source. What followed was a “box office” FaceTime call that would be worthy of any transfer thriller.
The mutual respect between Mourinho and Messi was evident even at formal events, years before their secret transfer discussions.
The Special One’s Masterful Pitch
Mourinho broke the ice with the kind of psychological flair that defined his career. “Hi Leo, I’m Jose!” he began, before launching into a monologue that perfectly balanced flattery with cunning strategy. He confessed to countless sleepless nights devising plans to stop the Argentine genius, only for Messi to always find a way to win.
In a stunning twist, Mourinho then advised him to stay at Barcelona. “They’ll build you a statue there,” he insisted, positioning himself not as a predator but as a confidant. Then came the masterstroke. He told Messi that if there ever came a day when the coffee didn’t taste right and the sky turned grey in Catalonia, then he should “open the gate of happiness again,” and behind it, he would find Jose Mourinho waiting.
It was a checkmate move. Messi was reportedly captivated, convinced that under Mourinho, he could “win whatever I want.” Personal terms were swiftly agreed upon: a net salary of £50 million per season and 70% of his image rights. The release clause? A cool €250 million, which Chelsea were prepared to pay in full.
The Deal That Vanished Like a Soap Bubble
With Messi‘s approval, the wheels were in motion. A formal meeting was arranged at Chelsea’s headquarters with the powerful director Marina Granovskaia. The intermediaries, already dreaming of their massive agent fees, were chauffeured to Stamford Bridge in a long Mercedes. Everything was progressing perfectly.
However, the plan had a critical flaw: it was operating outside of Messi’s primary representative, his father and agent, Jorge Messi. The clandestine nature of the talks, orchestrated by Deco and other friends, meant Jorge was kept in the dark. The house of cards came tumbling down when Cesc Fabregas, a close friend of Messi who had just signed for Chelsea, excitedly approached Mourinho about the news. This inadvertent revelation allowed Deco to alert Jorge Messi.
Messi had many battles at Stamford Bridge as an opponent; a move to Chelsea would have rewritten his legacy in London.
A furious Jorge called his son for an explanation. In a moment that highlights the powerful family dynamics at play, Leo Messi completely denied any knowledge of the talks or any desire to leave Barcelona. As Di Marzio poetically describes it, the entire deal burst “like a soap bubble that vanishes in thin air, without leaving the slightest mark.”

The Legacy of the Missed Opportunity
This story, expertly detailed in Gianluca Di Marzio’s book Grand Hotel Calciomercato, remains the “biggest unknown tale in the transfer market.” It underscores the immense influence of family in a player’s career and the complex, often secretive, world of high-stakes transfers.
For Chelsea and Abramovich, it was a bitter pill to swallow. They had been within touching distance of securing the greatest player of all time, convinced by a manager’s charm and a player’s momentary frustration. For Messi, he remained a one-club legend for several more years, continuing to renew his contract with Barcelona and achieving even greater heights.
Gianluca Di Marzio’s work continues to be a trusted source for uncovering the hidden stories of the football world, much like the insights we provide at Krikya.
How Chelsea almost pulled off the great coup
The allure of this story is undeniable. It makes us wonder how the landscape of the Premier League would have changed with Lionel Messi in it. Would he have dominated English football as he did La Liga? Would Chelsea have established a lasting European dynasty? While we’ll never know the answers, the tale itself is a fascinating glimpse into the world of what could have been.
What do you think? Would Messi have been a success in the Premier League? Share your thoughts and join the conversation. For more incredible football insights and untold stories, stay tuned to Krikya.