In the last summer mercato, AC Milan club management tried many times to find solutions to offload Spanish winger Samu Castillejo after a disappointing spell with the team. he is no longer the starter as Alexis Saelemaekers now occupies that flank and rotates with Alessandro Florenzi when needed.
The Spanish winger is no longer needed by Stefano Pioli who does not include him in his plans. According to what is reported by Calciomercatoweb.it, Castillejo's return to La Liga is a possibility. But now, there is a chance for him to join the English Premier League.
The source reports that Castillejo could actually join Tottenham Hotspur as part of an exchange deal that sees Milan send the Spaniard and receive in return young talented midfielder, who is not finding any space with the London-based club, Harry winks.

Caughtoffside.com report that Harry winks is set to leave Tottenham in January's transfer market.
AC Milan, therefore, could consider this opportunity. They would offload a surplus player in Castillejo and sign instead a talented midfielder in a convenient move, given that Franck Kessié's situation is unclear. Calciomercatoweb.it conclude by pointing out that Castillejo-Winks is an idea which would satisfy both clubs. However, an amount of of 4 to 5 million euros will need to be paid to Tottenham as part of the deal.