Jamie Redknapp says that Andre Villas-Boas did not know when to pick his fights and ultimately lost the war.
Chelsea sacked Villas-Boas on Sunday a day after a 1-0 defeat at West Brom which was the final straw after a dismal run of results that have put their Champions League qualifications in doubt.
And while Redknapp believes Chelsea cannot continue go through managers like they do, he says that Villas-Boas did not help himself.
"I think the Napoli game was the tipping point for him," said Redknapp on Sky Sports News HD.
"On the night he left out Ashley Cole and Frank Lampard and I think people forget that he also fell out with (Nicolas) Anelka and during the season (Didier) Drogba has been dropped as well.
"I just think that as a manager you have to show experience in terms of waiting for the right time to take on the senior players. I think at times he was picking fights that he did not need to.
"He had experienced players who could still offer him a lot and by not playing them and not using them I just felt that he made so many problems by not doing that. I think he misjudged it badly.
"I'm afraid the way Chelsea keep on sacking managers just isn't going to work. Look at Manchester United, Arsenal - they have continuity."
Redknapp's fellow Sky Sports pundit Alan Smith says that Chelsea took a chance with Villas Boas and that just did not pay off.
"It was a huge gamble to employ a 33-year-old with so little top-flight experience at a place like Chelsea," said Smith. "You have got to be a strong manager, so at the end of it I am not particularly surprised."
Smith also agreed that it was about time a Chelsea manager had the authority and the backing of the owner.
"There has to come a time when the manager is the top man at that football club and that has not existed for a while now," added Smith.
"The manager has to call the shots and if the senior players are not happy then the owner has to back his manager.
"I think at times AVB cut of his nose to spite his face in terms of dropping people when it was not the best decision for the team in my opinion.
"But you have got to give your manager authority, that is the only way it will work."