‘I Started Crying!’ – Rafael Leao Reveals How Dream Benfica Career Fell Apart as Club Left Him ‘Waiting for a Van’ Before He Quit for Fierce Rivals Sporting

Rafael Leao’s Failed Move to Benfica and Early Heartbreak

Football careers often hinge on the smallest of details. A single decision, a broken promise, or even the absence of a van can shape the destiny of a future superstar. For Rafael Leao, now dazzling Serie A crowds in AC Milan colours, the story of his youth could not better illustrate this.

Leao has revealed that his childhood dream of playing for Benfica, the club both he and his father adored, crumbled before it even began. Despite signing with the Lisbon giants’ academy, the young winger never actually trained a single day with the Eagles. Why? Because the club failed to provide the transport they had promised—a van meant to collect him from school and take him to training sessions.

Instead, the teenager was left standing outside, waiting day after day. The van never came. After a week of disappointment, Leao broke down in tears, his dream in tatters. Soon after, he would swap allegiances to Benfica’s fiercest rivals, Sporting CP, where his professional journey truly began.

Leao Recalls the Benfica Story: “I Started Crying”

Speaking on the SayLessGlobal Podcast, Leao revisited those painful early days with a mixture of humour and regret.

“Benfica wanted me to sign. My dad said yes; he’s a Benfica fan too. I signed for Benfica, but since my dad didn’t have a car at the time, I couldn’t get to training,” he recalled. “Benfica said, ‘Don’t worry, sign the contract and we’ll have a van to take your son from school to training.’

“I waited for the van. The van never arrived. The second and third days were the same. A week went by and I started crying. I didn’t even get to do a training session. That’s when we decided to sign for Sporting.”

For a boy whose entire childhood dream revolved around wearing Benfica red, the emotional impact was devastating. Yet, in football, as in life, closed doors often lead to new opportunities.

From Benfica’s Rejection to Sporting’s Embrace

Sporting welcomed Leao, offering him the environment and structure that Benfica failed to provide. He would spend seven years in Sporting’s academy, climbing through the ranks and honing the raw speed and skill that would eventually make him one of Europe’s most feared wingers.

His big break came in February 2018, when then-coach Jorge Jesus handed him his senior debut. Just weeks later, Leao made history by scoring against Porto, becoming the youngest Sporting player ever to find the net in that fiercely contested fixture.

That goal wasn’t just a milestone for Sporting; it was also poetic justice for a boy who had once cried waiting for Benfica’s van. In the most heated rivalry in Portuguese football, Leao had chosen the green half of Lisbon, and he delivered.

Violent Attack Ends Sporting Chapter

AC Milan v SSC Bari – Coppa Italia

But Sporting wasn’t to be Leao’s forever home. Later in 2018, the winger’s time with the club came to an abrupt end when a violent mob of fans stormed the club’s training ground, attacking players and staff.

In the aftermath, Leao terminated his contract, citing unsafe working conditions. For many young players, such turmoil might have derailed a promising career. For Leao, it was another turning point. He would soon head abroad to pursue his professional ambitions.

Rui Costa’s Apology Years Later

Time, however, heals wounds—and in football, apologies sometimes arrive decades late. Leao revealed that Rui Costa, now Benfica’s president, recently met his father and addressed the mishap.

“A few months ago, my father met with Rui Costa, and they started laughing,” Leao explained. “He said, ‘I apologise for what happened to your son, for not having come to pick him up.’”

The apology was lighthearted, but for Leao, it was confirmation of how close his path had been to wearing Benfica red. Instead, fate sent him down another road—one that would take him to France, Italy, and global stardom.

The Leap Abroad: AC Milan and Redemption

In 2019, Leao made a career-defining move to AC Milan. His early days at San Siro weren’t easy. With just six goals in his first season, many critics questioned whether the Portuguese youngster could live up to his billing.

But Leao persevered. The breakthrough came during the 2021-22 season, when he helped fire Milan to their first Scudetto in over a decade. With 11 goals and 10 assists, he not only became a fan favourite but also earned the Serie A MVP award. His fearless dribbling, devastating pace, and eye for goal made him a nightmare for defenders and a joy for neutrals.

Transfer Rumours and Loyalty to Milan

Success inevitably brought transfer speculation. In the summer of 2025, Leao was linked with European heavyweights Bayern Munich and Barcelona. Yet, rather than chase a move, the 26-year-old committed his future to Milan.

Coach Massimiliano Allegri was quick to praise his decision, hailing Leao as “the centrepiece of this project.” For Milan, keeping him was as good as signing a world-class player. For Leao, it meant loyalty to the club that had made him a champion.

Recovering from Injury and Future Goals

Udinese Calcio v AC Milan – Serie A

Currently sidelined with an injury, Leao’s focus is on returning to full fitness. Milan need his brilliance as they chase their 20th Scudetto title, a milestone that would further cement the club’s historic legacy.

Beyond domestic glory, Leao has ambitions to shine on the international stage. With the 2026 World Cup on the horizon, he wants to be at his peak for Portugal, ready to add another chapter to his story.

From Tears to Triumph: The Leao Journey

Leao’s tale is more than just another football anecdote. It’s a reminder that careers are shaped not just by goals and trophies but by human moments—by broken promises, tears of frustration, and unexpected turns.

The boy who cried waiting for Benfica’s van could have been lost to football’s cruel unpredictability. Instead, he became one of Europe’s brightest stars, embraced by Sporting, matured in France with Lille, and crowned in Italy with Milan.

Conclusion: A Van That Changed Everything

In the end, Rafael Leao’s career is a story of resilience. Benfica’s broken promise sent him across Lisbon to Sporting, where he launched his career. A violent attack ended that chapter, but opened the door to international stardom. At Milan, he has blossomed into a superstar, adored by fans and respected across Europe.

When he looks back, the memory of waiting outside for a van that never came may still sting. But without that van, there might never have been the Sporting goal against Porto, the Scudetto at Milan, or the dazzling runs that light up San Siro.

As Leao himself might say: sometimes disappointment is just destiny in disguise.