Tottenham were beaten by Chelsea on Saturday and Jose Mourinho might choose to add a Blues player to his ranks in the summer.
The current Spurs boss signed Willian for £30 million back in 2013 and he has since made 325 appearances for the Blues.
It is thought that the 31-year-old is keen to sign a new three-year contract but Chelsea only want to give him two.
As a result, the winger could leave on a free during the summer and that could be music to the ears of Mourinho.
It is thought that Willian is still in regular contact with Mourinho too and he would surely relish the chance to link up with his former boss at Tottenham.
He told the Daily Star: “People ask me about the best coaches I have had. For sure, Mourinho is one of them.
“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 have played well he would also say something like, ‘today you killed it’.
“Even after he left Chelsea he spoke well of me. We are still friends. Sometimes we exchange messages.”
Tottenham have found themselves in the midst of an injury crisis this season. Both Harry Kane and Son Heung-min have suffered serious problems, leaving Mourinho without a recognised centre forward.
Although Willian isn’t a striker, he would ensure more competition for places in the final third and Mourinho will want to avoid such a mess next season.
Ultimately failing to land a talisman during the January window could scupper Spurs’ plans of Champions League football next season.
Willian can play on either flank or as a No.10 and his Premier League experience would make him a quality signing on a free.
The £120,000-a-week speedster has scored five goals and registered five assists under Frank Lampard this season; although a large percentage of his game time as come off the bench.
The Tottenham board may cut Mourinho some slack this season if they fail to reach the Champions League.
Mauricio Pochettino oversaw something of a hangover from last year’s final and Spurs were some way off the pace when Mourinho arrived.
Next season will be on the Portuguese boss, however, and he must ensure that if he misses out this time around, he finishes in the top four next season.
Players like Willian will help him achieve that. It would appear that the Brazilian is keen to work with him again and Tottenham could secure a shrewd piece of business if they can get a deal over the line.