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Former Chelsea scout and managerial prodigy Andre-Villas Boas was famous for inventing new words, trying to play a high-line, saying PROJECT a lot, and being a pretty spectacular failure in the SW6. He remains the only full-time Chelsea manager to have won fewer than half of his matches (19 from 40).
What began as a tenure awash with great hope and new ideas ended in dressing room strife, a crisis of confidence, maybe some carbonite, and some truly palpable discord on and off the pitch. Villas-Boas went from young stud manager to an object of ridicule rather quickly, though he did inspire at least one of us to budding greatness.
In fairness to AVB, he picked up the pieces quickly and effectively since then. He managed to make Spurs mildly successful for a bit (better record still than Pochettino) and then went to Russia for a couple years, where he won the league with Zenit St. Petersburg before resigning this summer to spent time with family in Portugal. And while before he'd also spent some time complaining about the way he was treated in England, he's recently revised that view to perhaps a more realistic one.
"The Chelsea experience was too much too soon. I wasn't flexible as a manager at that time. I was communicative, but I wasn't flexible in my approach. At Tottenham I learnt to be different."
"In professional football you have to live the day-to-day. The objective is the group performance, but every single individual requires a different response from a manager. You can't be the same person to each player. At Chelsea the group was more important, I stuck to my methods too much."
-Andre Villas-Boas; source: Express
AVB's failure at Chelsea is still being felt to this day, as the Blues try once again to somehow transition the team out of the Old Guard era, and created sustained excellence with the next generation. Mourinho's title-winning season has proven to be a one-hit wonder, a short-term success story of a team built to win now rather than built to be strong for years to come. The need for transition at Chelsea was already evident when Villas-Boas took over; here we are now five years later, still trying to solve many of the same problems.
Obviously, it hasn't been all bad. AVB's sacking led to the most magical two and a half months with Di Matteo in charge, the arrival of the likes of Eden Hazard and Oscar and the unsustainable fun of the MaZaCar ... followed by dark Interim days. The second Mourinho era then ended just as the first, so here we are trying to build it up again, with Conte in charge.
Conte, just as AVB did, has a few radical ideas that could lead to a solid future. Crucially, he seems to be more flexible in terms of looking for solutions and seems to have a much better handle on the man-management side of things (managing up, down, and across the organization) so hopefully he can weather the stormy waters much better than his then younger, brasher, boy-scoutier Portuguese counterpart.