Thomas Tuchel and Todd Boehly are currently struggling with an issue that has caused problems for previous Blues managers, and the situation is finally set to hit crunch time.
With 10 first team players out of contract next summer, all of them available to speak to other clubs from January, the Blues could be about to make a loss if none of the players renew or extent before then.
The group has been purchased by five separate managers and most of them no longer have a future at the club, with half of them having not played a significant role in any of the club's success over the past decade.
READ MORE: Thomas Tuchel must overcome 7-year Chelsea pre-season issue if Blues are to remain in contention
It is a staunch reminder for Boehly that the squad he inherited still represents the structural issues that he wishes to overhaul during his time at the club. It is not something that he can just ignore though. He may not have spent any of the money to bring those players in, a collection that spans from Cesar Azpilicueta's successful £7m bargain in 2012 to the long-term loanees Kennedy and Matt Miazga, they are currently Boehly's and Tuchel's problem.
Chelsea's historic inability to move on from underperforming players and even more so their reluctance to let them go for cheaper than they were bought for, has meant a stockpile that crowds out Tuchel's current squad. It has had a knock-on effect for his pre-season preparations and could cause significant damage to Chelsea's start to the season if it isn't dealt with quickly.
There is an option for several players to stay on, Thiago Silva will likely be afforded the option to trigger a second one-year extension if he wishes, at least one of Jorginho or N'Golo Kante may well be offered a new short-term contract of their own and Marcus Bettinelli likewise may remain at the club.
The issue is that for Ross Barkley, Kennedy and Michy Batshuayi, there is no quick fix. Clubs are not generally interested in taking on players that have struggled for form over a long period of time and are on large wages, especially not when they could be signed for free or on a cut-price deal in six months time.
This leaves Tuchel with three players that are unlikely to feature much, if at all, in his plans next year, and if anything it clogs up his squad and reduces the chance of looking at and giving younger players an option. Unlike Tottenham and Antonio Conte, Tuchel took the strange decision to allow these players another chance on the tour of America, while Spurs left their fringe players behind.
The additional issue is how to get rid of players on longer-term contracts with even larger wages and much bigger prices. In this bracket is Kepa Arrizabalaga, Timo Werner, Hakim Ziyech and Christian Pulisic. They cost Chelsea a combined figure of around £35m a year in wages alone, let alone the damage it causes Tuchel on the pitch to have unhappy players.
Ziyech, Werner and Kepa are all contracted until 2025, Pulisic until 2024, but realistically they would all like a way out now. With nobody likely to match their individual wage packets or offer enough money to satisfy even Boehly, who has no direct ties to their initial value, Chelsea can't afford to have them kept on their books year after year. It doesn't make sense in a business perspective or playing one either.
The American owner might have the answer, at least a temporary one, as Chelsea are prepared to start using the loan market for their senior players, reports The Athletic. This comes alongside the news that Chelsea are reportedly in talks to allow Kepa to join Napoli on loan next season, whilst Ziyech has already held initial talks with AC Milan that involves a loan element to a deal to take him away from London permanently.
Werner has also been offered around in a similar capacity. Juventus are said to be still interested in his signing despite a swap deal for Matthijs De Ligt not progressing, and former club RB Leipzig could also be a possible destination for him. The trick will be for Chelsea to work on offloading some of the wages involved in these deals, possibly splitting the payments between the clubs, or even attempting to persuade the players to lower their demands.
Without the loan market, which still doesn't provide a long-term solution, the Blues will be in a tough position to bring in the extra four players that Tuchel is after.
READ NEXT:
Three winners and four losers from Chelsea pre-season tour amid Thomas Tuchel frustration
Chelsea news and transfers LIVE: All the latest updates and rumours from Stamford Bridge
The £180m attacking problem that Todd Boehly must solve this summer at Chelsea
Chelsea's own Kylian Mbappe transfer plan as Blues target Newcastle ace with £50m value
