Top 15 Biggest ‘What If’ Careers in Football – Ranked

June 27, 2025 Oliver Obel

In football, talent alone doesn’t guarantee success. While many stars go on to fulfil their potential, others are held back by injury, poor choices, or external circumstances. These 15 players, despite immense promise and global fame, left fans wondering what might have been.

15. Antonio Cassano

Cassano was a generational talent, blessed with vision, creativity, and confidence. However, poor discipline, clashes with coaches, and off-field distractions plagued his career. He could’ve been a legend — if only he had stayed focused.

14. Alexandre Pato

Pato had Europe at his feet after exploding at AC Milan. Sadly, muscular injuries and misjudged career moves — including a switch to China — cut short his prime years. His career remains a case of enormous potential gone unrealised.

13. Jack Wilshere

Wilshere had everything to become England’s midfield engine — technique, fearlessness, and vision. But relentless injuries stalled his development year after year. He retired at 30, leaving behind only glimpses of what could’ve been.

12. Andy Carroll

Carroll’s raw physicality and aerial dominance made him a fearsome forward. A record-breaking transfer to Liverpool signaled big things, but injuries and inconsistency limited his impact. He never lived up to his early hype.

11. Dele Alli

Dele was once England’s golden boy, dominating midfield with flair and goals. He peaked young, but lost momentum due to off-field issues and apparent burnout. Now, his fall from grace feels like one of football's most dramatic.

10. Abou Diaby

Diaby had all the tools: power, finesse, and tactical intelligence. But a brutal tackle early in his Arsenal career sparked a nightmare of recurring injuries. He played just a handful of games each season thereafter, always fighting to stay fit.

9. Philippe Coutinho

Once the centerpiece of Liverpool’s attack, Coutinho earned a blockbuster move to Barcelona. Instead of flourishing, he became one of football’s most expensive transfer flops. Injuries and tactical misfits turned a star into a forgotten name.

8. Gareth Bale

Bale won it all at Real Madrid, delivering iconic Champions League moments. Yet injuries and waning club commitment — often overshadowed by his love for golf — left the feeling that he could have dominated even more consistently. His flashes of brilliance weren't enough.

7. Samuel Umtiti

Umtiti looked like France’s next great defender after his performances at the 2018 World Cup. But playing through injury for club and country took a heavy toll, leading to years of decline. His career trajectory changed drastically almost overnight.

6. Eden Hazard

Hazard lit up the Premier League with dazzling runs and big-game heroics for Chelsea. His move to Real Madrid should’ve been the final step to superstardom, but injuries and fitness problems derailed everything. He retired with more regrets than trophies in Spain.

5. Mesut Özil

Özil’s passing vision was pure artistry — at his best, he created chances nobody else could see. But as his career progressed, inconsistency, tactical issues, and early retirement from international football overshadowed his brilliance. He left behind a divided legacy.

4. Kaka

Kaka was the last player to break the Messi-Ronaldo duopoly, winning the Ballon d’Or in 2007. His move to Real Madrid was meant to elevate him further, but injuries drained him of the explosiveness that once made him unstoppable. His peak was glorious, but too short.

3. Marco Reus

Loved for his loyalty and elegance, Marco Reus had the skills to be a Ballon d’Or contender. Unfortunately, his career has been marred by constant injuries, especially ahead of major tournaments. We’ll never know how high he could’ve soared fully fit.

2. Ronaldo Nazário

Few players have ever been as explosive or complete as Ronaldo Nazário. Despite winning two Ballon d’Ors and a World Cup, devastating knee injuries robbed him of his physical prime. He was incredible — but he could’ve been the undisputed greatest ever.

1. Ronaldinho

Ronaldinho was football’s ultimate entertainer — a player who redefined joy on the pitch. At his peak, he was untouchable, winning the Ballon d'Or and leading Barcelona to greatness. But his lack of discipline and fading motivation saw his decline come far too soon.