Chelsea have had the unique privilege of seeing many of their modern greats bow out at the right moment.
Gianfranco Zola left just before Roman Abramovich's injection of wealth in 2003 but his final match concluded in a defining win over Liverpool to claim a vital Champions League spot. His legacy is intact as one of the most beloved talents to ever grace the turf of Stamford Bridge.
John Terry probably got the sweetest of all send-offs by lifting one more Premier League title and getting to say his grand farewell to an emotional Stamford Bridge crowd.
Although both Frank Lampard and Ashley Cole didn't quite get the same send-offs in 2014 to their playing careers, it felt like the right moment to start a new chapter even if it came with a bittersweet feeling.
Didier Drogba probably has the rare accolade of coming back after his fairytale ending in 2012 to lift another Premier League title under Jose Mourinho and be carried off the pitch by his teammates on the final day of the 2014/15 season.
Eden Hazard's injury issues post his Chelsea career have probably signified why his 2019 departure after one last night of genius in Baku proved the suitable full stop in west London.
Most recently Willian and Pedro's parallel exits at the end of the 2019/20 campaign felt like the right point for two stalwarts of the first-team squad to move on.
These are all examples to Marina Granovskaia as to why "losing" a contract negotiation is not the end of the world, in fact for the natural health of a squad it is essential.
Era's by their very definition have a beginning and end. The problem comes when assessing when is the right moment to roll the credits.
We have a few examples of players staying maybe too long. Branislav Ivanovic, once a talismanic presence in Chelsea's defence losing speed and was exposed regularly at the start of the torrid 2015/16 season.
To a much lesser extent the feeling that Marcos Alonso, a trailblazing presence in Antonio Conte's title-winning charge, now looks like a player behind the pace of Tuchel's vision. A representation of what needs to change rather than being a youthful presence to enact it himself.
This all comes back to the dilemma over Cesar Azpilicueta's future at Stamford Bridge.
The club captain completed the grand slam of silverware in Abu Dhabi last weekend with the FIFA Club World Cup and could add even more glamour onto a ridiculously trophy-laden CV in his almost 10-year stint with Chelsea.
As was proven in the Club World Cup and his charging presence against Plymouth, Azpilicueta still feels he has much left to give even if he's competing for minutes against younger legs like Trevoh Chalobah.
It is why Barcelona are seriously interested in signing him this summer and why there probably is an internal fear that losing such a respected figure woven into the foundations of Chelsea could be an error.
But there have already been signs the Spaniard is on a downwards curve. His tireless running at wingback cannot provide the speed necessary for Tuchel's system and the interest in Sevilla's versatile defender Jules Kounde indicates a succession plan.
The last thing a highly respected legend like Azpilicueta needs is to be seen as someone out of place. A reality Ashley Cole once faced up to when a younger Azpilicueta took his spot in Mourinho's team eight years ago.
A similar dilemma is also presented with both N'Golo Kante and Jorginho, two players out of contract in 2023 in an area that is on the brink of a revamp.
Even if Azpilicueta will not be technically sold given his contract expires this summer, his departure would be a signal that an era has ended and a new one can begin, probably at the right moment.
Make sure you have subscribed to CareFreeChelsea on YouTube! The Fan Brands team along with plenty of your football.london favourites will be producing daily Chelsea content for you to enjoy including match reactions, podcasts, football fun and interviews. You can follow Daniel Childs from the CareFreeChelsea team to keep up to date with his work. If you enjoyed reading this then give my other articles a read below.