This transfer window was always going to be about patience as most teams had to wait for other deals to happen or to sell some players to raise funds to allow them to spend in the market.
AC Milan did make an early move to sign Olivier Giroud from Chelsea, but it looks like their long-term pursuit of Tiemoue Bakayoko is still ongoing:
AC Milan are also closing on Alessandro Florenzi deal with AS Roma – final details to complete the agreement for the new right back. ?? #ACMilan
— Fabrizio Romano (@FabrizioRomano) August 17, 2021
At this stage, the most logical thing for Chelsea would be to sell him on a permanent basis. He’s been out on loan several times so it’s clear that he’s not going to impress to the point that they’ll give him another chance, while his market value is unlikely to change much so another loan spell doesn’t really put him in the shop window either.
One of his many loans was with AC Milan so both parties know each other well, but it’s not clear if Chelsea could offload him permanently or if it would be some kind of loan deal with an obligation or an option built in.
Chelsea still have a need to sign another centre back and Bakayoko could raise a reasonable fee in the market, so they’ll be hoping an agreement