While the prospect of Josh Windass joining Brazilian side Santos may sound like the byproduct of a hallucinating AI, it almost happened in the January transfer window.
The 31-year-old attacking midfielder is currently a part of Sheffield Wednesday’s push to make the Championship play-offs and began 2025 in style, scoring from inside his own half against Derby County last month, one of ten goals he has netted for the Owls this term.
The son of Hull City legend Dean, Windass signed up at Hillsborough in 2020, the latest stop in a career which began with Harrogate Railway and has taken in stints with Accrington Stanley, Rangers and Wigan Athletic, but for a while last month, it looked like he may be heading to one of South America’s most iconic sides.
Josh Windass discusses his potential Santos move
The link came about due to Santos now being managed by Pedro Caixinha, Windass’ former Rangers boss, with the pair working together between March 2017 and October 2017.
Caixinha took charge of Pele’s former side in December 2024, inheriting a side that had just been promoted from Brazil’s Serie B and the former Gers chief was looking to add more attacking talent to his team.
Alas, Caixinha and Santos did not secure a deal for Windass, as the club moved to re-sign their former star Neymar, who was available again after Al-Hilal terminated the 32-year-old’s contract by mutual consent following an injury-hit spell in the Saudi Pro League.
Neymar began his career with Santos, turning out 225 times for the team and scoring 136 goals, becoming on of world football’s hottest young properties and earning a big-money move to Barcelona, where he would win two La Liga titles and a Champions League.
Windass has now had his say on how the move went down, admitting that the whole episode caught him off guard.
“I’ve seen all the stories, I’m not sure he [Neymar] was a back-up [for me], but I’ll keep running with it,” Windass told GiveMeSport.
“Being English, it’s quite unexpected when teams like that get involved. But obviously knowing the coach who’s managed me before, he contacted my agent at the beginning of the window and asked if there was any way a deal could be done.
“Obviously nothing materialised, but I’m happy where I am, so I’m not too disappointed, but it is what it is and it’s always nice to have interest from big clubs like that.”
In FourFourTwo’s opinion, it would have been great to see how Windass, who is valued at €400,000 by Transfermarkt, would have got on in the Brazilian top flight, but with Sheffield Wednesday enjoying a strong season and sitting just two points off the Championship play-offs, it’s easy to understand why he would choose to stay in Yorkshire.
