Given the relentless spending of Todd Boehly and Clearlake Capital since their arrival in May 2022, the Blues recently faced a battle to comply with the Premier League's Profit and Sustainability regulations.
With the issue having gone quiet in recent months, Chelsea were seemingly successful in achieving that goal, despite continuing to spend freely in the market.
Somewhere in the region of £177m is said to have been raised through player sales, some of the players in question commanding more lucrative contracts than others.
However, it was the departure of Conor Gallagher that divided opinion, the academy graduate having starred under previous head coach Mauricio Pochettino at a time when he was also made club captain.
Although Gallagher had less than a year on his contract before leaving for Atletico Madrid, many have questioned the logic of selling a much-loved player who was committed to the club.
"There are misconceptions"
Head coach Enzo Maresca allegedly did not view Gallagher as a suitable fit for his style of play, the 24-year-old subsequently being removed from the senior group once it became apparent that his future was away from Stamford Bridge.
There are now fears among the fanbase that players possessing the same background could follow, like with Mason Mount in the year that preceded Gallagher's exit.
Nevertheless, speaking in an exclusive interview with The Telegraph, Winstanley has insisted that there is not a blanket approach to homegrown talent, revealing that offers were rejected for other such talent.
He said: "We had a significant offer for one of our academy products this summer that we absolutely chose not to take. There's a lot of misconception out there.
"We've had two debuts this year. There's three or four more players in behind who we think we can push through this year as well that we're keen to do. The manager's on board with that, he's aware of the players coming through. We give them opportunities when we can to make sure they've got that pathway.
"It's not just about PSR, it's contractual statuses, it's circumstances. The two players you referenced, there were contractual problems that we walked into. It's really important for us to bring through players."
Who are Chelsea's future?
In terms of academy graduates who can now be regarded as senior players, Reece James and Levi Colwill are the solitary such names.
That said, defender Josh Acheampong and winger Tyrique George have been identified as two prospects who could have a long-term future at the West Londoners.
Midfielder Kiano Dyer, who is just 17 years of age, was also recently selected on the substitutes' bench for the Conference League game with Gent.