Jose Mourinho worked with Willian at Chelsea during his second spell at the club and has reportedly identified him as a target.
According to the Daily Star, Mourinho was also keen to sign the Brazilian during his final year at Manchester United.
However, the Portuguese manager's sacking ended any pursuit of the player from Man United's end.
Mourinho's plan involved selling Anthony Martial, which apparently didn't sit well with club vice-chairman Ed Woodward.
But Mourinho may get another bite at the apple now that he's in charge of Tottenham Hotspur.
The same report states that Spurs could be set to take advantage of Willian's contract situation at Chelsea.
The 32-year-old has less than six months left on his current deal which means he is free to negotiate with potential suitors.
It was rumoured that Barcelona were keen to take Willian in the summer, having retained their interest from two years ago when they lodged a £50m bid.
Although, Barcelona's desire to sign a long-term replacement for Luis Suarez, 33, is due to take priority instead.
That, in turn, clears the way for Mourinho to make a move for his former player Willian - who is a fan of his old boss.
"People ask me about the best coaches I have had. For sure, Mourinho is one of them," he said.
"We had a special relationship. He demanded a lot, so there were some conflicts, but that’s normal.
"He would challenge me and call out my mistakes, but if I had played well he would also say something like, ‘today you killed it'"
Willian nearly joined Spurs before Chelsea famously gazumped their London rivals in the eleventh hour.
The event has a significant place in Chelsea fans' hearts, who even made a song about the transfer victory.
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