The 31-year-old Brazilian will end his seven-year stay at Stamford Bridge when his contract expires this summer.
Arsenal and Liverpool have been linked with Willian but according to Keys he is poised to reunite with Jose Mourinho.
Speaking on the Keys & Gray show, the football host seemed more than confident of his claim:
“He’s (Willian) another one that has already spoken to Jose Mourinho, he’s on his way to Tottenham,” Keys insisted.
Tottenham are expected to have a reduced budget this summer due to the impact of the Coronavirus, and Willian would be a shrewd freebie.
Willian and Mourinho worked together at Chelsea with the Brazilian known to be a favourite of Jose.
In a recent interview, Willian said: “Nothing arrived from Mourinho but we do have a good relationship. He’s a big friend of mine.
“We speak to each other sometimes but when it comes to that (transfers) he respects me a lot.”
Willian and his family are settled in London, raising the chances of a Spurs move despite their rivalry with Chelsea.
“I like London and my family likes it too, but that’s a question I don’t know how to answer,” he said when quizzed on his future.
“I don’t know which club I’m going to or if I’m staying here at Chelsea. Or if I’m leaving to another London club. Or if I’m leaving England, that’s something I don’t know.”
Spurs almost signed Willian in 2013 before Chelsea hijacked the deal, landing the Brazil international from Shakhtar Donetsk in a £30m deal.
The investment has proven to be a good one for the Blues, with Willian helping the Club win two Premier League titles and the Europa League.