Petr Cech is thought to be considering his position after Chelsea's reshuffle of the board after excelling through his working relationship with Roman Abramovich.
The legendary former Chelsea goalkeeper hasn't made a decision yet on whether to continue or leave and it will hinge on further talks with Todd Boehly, who has placed himself in a prominent role after the takeover.
Boehly has become both the chairman and interim sporting director after working day-to-day in those roles since taking over the club at the beginning of June.
Who decides on Chelsea's transfers after the board reshuffle?
Boehly is now in charge having been pivotal in the decision to loan Romelu Lukaku to Inter for a cut-price, a decision which was supported by manager Thomas Tuchel.
The £100 million ($136m) club-record signing from last summer was let go for just an £6m ($8m) loan fee with a further £2m ($2.5m) available in performance-related add-ons.
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During the process, Boehly conducted meetings with Inter and has been approving deals across the men's, women's and academy teams.
He has been working on relationships with Tuchel, academy director Neil Bath and women's manager Emma Hayes.
Former transfer boss Marina Granovskaia has continued in an advisory role, offering her contacts to Boehly as the club aims to successfully navigate the transfer window.
After that, they will appoint a new sporting director, which will leave Cech needing to define his role in the future.
He currently operates as a technical and performance advisor and has been central to a host of signings since his appointment.
The issues have arisen because Chelsea opted for an unusual structure under the former owner that saw Granovskaia signing off transfers without a sporting director, taking advice from Cech and the scouts directly.
She acted on behalf of the former owner Abramovich, but that atypical football structure will now be completely scrapped after the transfer window is complete.
What will Chelsea do in the transfer window?
The clearing of Lukaku from the striker position allows the Blues to sign an attacker and Manchester City's Raheem Sterling is among a host of targets for the role.
There are further defensive targets in Lens's Jonathan Clauss, RB Leipzig's Josko Gvardiol, and PSG's Presnel Kimpembe, among others.
They have been in active negotiations with U.S. men's national team goalkeeper Gabriel Slonina, who is expected to be loaned back to the Chicago Fire until the end of the MLS season in the winter.
Chelsea are ambitious for this transfer window but the takeover has left the club needing to rebuild to replace Antonio Rudiger and Andreas Christensen, who left for Real Madrid and Barcelona respectively.
Furthermore, they are behind other big clubs on negotiations due to the sanctions placed on them under Abramovich.