Having signed Jorginho in the summer, as well as hiring Maurizio Sarri as boss, the Blues are prepared to try their luck for a third time.
According to Calciomercato, the West Londoners are in talks with the Serie A side as they look to lure the Albanian international to the Premier League.
They claim that Chelsea have opened negotiations with Napoli due to their fear that they could be slapped with a two-year transfer ban.
Hysaj, 24, boasts a £44.5million release clause, but Chelsea are confident they can nab him cheaper as they would send him back on loan for the rest of the campaign.
The Italian outlet also reports that Napoli and the Blues made a "gentlemen's agreement" to stop Sarri from signing any more of his players following the transfer of Jorginho.
But with a potential transfer embargo on the horizon, Chelsea are continuing to press ahead with the move.
It is understood that Hysaj – tied down at Stadio San Paulo until 2021 – would be willing to be reunited with Sarri having spent three years under him.
The ex-Empoli has featured in over 150 games since joining Napoli in 2015, and has appeared in 16 matches in all competitions this season.
Should he make the move to join Chelsea, he will likely replace Davide Zappacosta, who could depart the club in the summer.
Manchester United and Liverpool were both believed to be in the hunt to sign Hysaj last campaign.
While the player's agent dropped a major hint of his future in November where he stated a move away from Napoli could be imminent.
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