Leandro Damião was once one of the most persistent names in Tottenham Hotspur’s transfer gossip.

For several years, the Brazilian striker seemed to be permanently hovering around the edges of Spurs’ plans.

Yet he never made it to north London — and his career ultimately took a very different path.

In 2011, Internacional said they had rejected a Spurs bid for the then 21-year-old, while reports put the proposed fee at around €12 million. Sky Sports reported at the time that Internacional had turned down the opening offer.

Damião was already a Brazil international and had developed a reputation as one of South America’s most exciting strikers.

The links only intensified after he impressed at the 2012 Olympics, where he finished as the tournament’s top scorer.

André Villas-Boas then publicly confirmed Tottenham’s interest, describing Damião as a player the club followed and one who fitted their profile. The Guardian reported on Villas-Boas’ comments, with Spurs continuing to monitor the striker.

By January 2013, Tottenham were still trying. The Guardian reported that Spurs had made a late offer of around £13 million, but Internacional’s valuation was far higher. Villas-Boas subsequently said the pursuit was effectively over.

And that was that. Tottenham moved on, while Damião’s career gradually lost the momentum that had once made him such a coveted prospect.

He stayed in Brazil with Internacional before moving to Santos, then had spells with Cruzeiro, Flamengo and Coritiba.

A move to Europe eventually came in 2016, but his brief spell at Real Betis produced just three appearances and no goals. He later found a more settled period in Japan with Kawasaki Frontale before returning to Brazil.

The contrast is striking. Damião was once being discussed as a potential Premier League star and a long-term Tottenham striker, but injuries and inconsistency meant he never quite reached the level many expected.

At 37, Damião is now playing amateur football in Brazil, having recently joined Parque Brasília in Campinas.

It is a remarkable final chapter for a player whose name was once almost synonymous with Tottenham transfer speculation.

Perhaps Spurs were right to keep trying — or perhaps they simply got lucky that the deal never happened. Either way, Leandro Damião remains one of the great ‘what if?’ stories of Tottenham’s transfer history.