First, Didier Drogba; then Ashley Cole and Frank Lampard; then Drogba again; then Petr Cech; and now, finally, John Terry - who will arguably be the biggest loss of them all when he eventually leaves Chelsea, whether it's this summer or not.
The Chelsea legend was at the centre of things in the 1-1 draw with Manchester United on Sunday thus proving his worth to the club once again. In the only four seasons where Terry has played in 95 percent or more of Chelsea's league games, The Blues won the title - in 2004-05, 2005-06, 2009-10 and 2014-15. To think that the club have not done so when he has features in less than that percentage of matches is pretty remarkable.
They managed to be champions last year without the services of Cole and Lampard - and Cech to a certain extent considering that he hardly featured - but without these club legends and Didier Drogba around the place to influence matters on and off the pitch, could this season's demise be a sign of things to come?
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Sunday's opponents won the title at a canter in Sir Alex Ferguson's last campaign of 2012-13, but it was a side whose spine was ageing and declining rapidly. Nemanja Vidic, Rio Ferdinand, Patrice Evra and Ryan Giggs all left and/or retired the year after Ferguson quit. It showed testament to the Scotsman's genius that he won the league so convincingly with a group of players who were past their best.
Another year would have surely been at least one too much for that group of players - whether it was with Ferguson or not - as it proved under David Moyes. However, it wasn't only their on-the-pitch skills that were missed, but their personalities and experience off it as well. They helped guide and integrate youngsters and new signings alike through the drills and attitudes of what it means to play for, and what it is that makes Manchester United the club they are and what they represent.
As we know, the Red Devils have been nowhere near the heights they reached under Ferguson in the three seasons since his departure. The manager himself was obviously a massive part of that, but the loss of stalwarts such as Vidic, Ferdinand, Evra and Giggs (although the Welshman is still at the club as Louis van Gaal's assistant) has contributed to the club's downfall.
The biggest void left at Man United was arguably that of their boss, which in Chelsea's case, doesn't seem to affect them in the trophy stakes even if they have 'only' won the league four times in 12 seasons. They coped for one campaign without Cole, Lampard and, to an extent, Cech, although the latter was still at the training ground, in the corridors influencing things. But however good Terry still is, he is not enough alone to pull players up from their stupor.
As he said himself: "I can tell people that they are great and it is really important I have got their backing because we have had so many managers over the last few years and it was important that myself and Didier and Lamps kept everyone together and said listen, as long as we keep doing our job, we are going to have the fans there supporting us.
"That is what matters, Chelsea Football Club, not the manager, not the players because one day we won't be here and it is important we keep the players going and keep the belief in our club to go on and win trophies."
Despite Chelsea's decent form since Jose Mourinho was sacked, which sees them sixth in the form guide (taking in the last six games), all dynasties like United, Liverpool and many before them are based on togetherness, spirit and being handy on the ball, but they all come to an end eventually.
When Terry leaves, Chelsea's fans will be hoping they won't be making a habit of being the sixth best side in the country - a position that Manchester United and Liverpool are becoming quite familiar with currently.