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When was Albus Dumbledore appointed as Headmaster? (this timeline is the result of discussion on the Loose Canon group)
'Only the Transfiguration teacher, Dumbledore, seemed to think Hagrid was innocent.' [CoS ch. #17; p. 230]
'How long have you been teaching at Hogwarts?' Professor Umbridge asked. 'Thirty-nine years this December,' said Professor McGonagall brusquely [OotP ch. #15; p. 287]
The one difference between the present-day office and this one was that it was snowing in the past; bluish flecks were drifting past the window in the dark and building up on the outside ledge. The younger Dumbledore seemed to be waiting for something, and sure enough, moments after their arrival, there was a knock on the door and he said, 'Enter.' Harry let out a hastily stifled gasp. Voldemort had entered the room. [HBP ch. #20; p. 412/413]
We know that Albus Dumbledore was the Transfiguration master at Hogwarts in 1943 (in Tom Riddle's fifth year), that Minerva McGonagall was Transfiguration mistress in the 1990s and that she started working at Hogwarts in December 1956 (because in September 1995 she tells Umbridge she's been there thirty-nine years come December). It is usually assumed, therefore, both that McGonagall took over the Transfiguration post from Dumbledore in 1956 and that that was the point at which he became Headmaster. This is reinforced by the fact that Minerva says she was appointed in winter, and Tom Riddle comes to see Albus soon after he became Headmaster and it is snowing.
However, we know that Remus Lupin was born in 1960, and that he was infected with lycanthropy as a small child. He speaks of Hogwarts policy regarding the admission of werewolves as if Dumbledore definitely became Headmaster after he was infected: and long enough after he was infected that his parents had had time to find out what the policy of the previous Headmaster was, and to be worrying about his future academic career. That would mean that Dumbledore became Headmaster some time in the 1960s.
[cut] 'Voldemort first approached Professor Dippet and asked whether he could remain at Hogwarts as a teacher.' [HBP ch. #20; p. 403]
Professor Dippet told him that he was too young at eighteen, but invited him to reapply in a few years, if he still wished to teach.' [cut] 'Which job did he want, sir? What subject did he want to teach?' [cut] 'Defence Against the Dark Arts. It was being taught at the time by an old Professor by the name of Galatea Merrythought, who had been at Hogwarts for nearly fifty years.' [HBP ch. #20; p. 404/405]
The house-elf returned within minutes, followed by a tall young man Harry had no difficulty whatsoever in recognising as Voldemort. [HBP ch. #20; p. 406]
'Help yourself, Tom,' said Hepzibah, 'I know how you love my cakes. Now, how are you? You look pale. They overwork you at that shop,' [cut] 'Mr Burke would like me to make an improved offer for the goblin-made armour,' said Voldemort. [HBP ch. #20; p. 407]
'Ten years separate Hokey's memory and this one, ten years during which we can only guess at what Lord Voldemort was doing ...' [cut] And Harry dived after Dumbledore through the shifting silver mass, landing in the very office he had just left. [cut] The one difference between the present-day office and this one was that it was snowing in the past; bluish flecks were drifting past the window in the dark and building up on the outside ledge. The younger Dumbledore seemed to be waiting for something, and sure enough, moments after their arrival, there was a knock on the door and he said, 'Enter.' Harry let out a hastily stifled gasp. Voldemort had entered the room. [HBP ch. #20; p. 412/413]
'I have returned,' he said, after a little while, 'later, perhaps, than Professor Dippet expected ... but I have returned, nevertheless, to request again what he once told me I was too young to have. I have come to you to ask that you permit me to return to this castle, to teach.' [HBP ch. #20; p. 414/415]
'Oh, he definitely wanted the Defence Against the Dark Arts job,' said Dumbledore. [HBP ch. #20; p. 418]
If we uncouple Minerva's arrival from Albus's appointment as Headmaster, what other clues do we have as to when he was appointed? We know that Tom Riddle came to see him soon after he was made Headmaster, and that this was ten years after Tom murdered Hepzibah Smith. We know that Tom joined Borgin and Burkes soon after he left school, which would have been in 1945 (we know it was 1945 because during the academic year 1992/93 we are told that the Chamber of Secrets was last opened fifty years beforehand, i.e. in academic year 1942/43, and that was Tom's fifth year). We know Tom was still working for Borgin and Burkes when he murdered Hepzibah.
What we do not know is how long Tom had been working for Borgin and Burkes before he murdered Hepzibah. But we do know that when Harry, who is himself sixteen at that point, sees a Pensieved memory of Tom talking to Hepzibah he looks to Harry like a young man. So we can assume that Tom is no older than thirty at the outside, and this is no later than 1957 (Tom turned thirty-one in 1957 - but not until the very last day of the year).
That means Dumbledore was appointed Headmaster no later than 1967 - probably some years less, but not earlier than 1963, to allow time for Remus to have been infected and his parents to have looked into his future educational prospects as a were. Circa 1963 or 1964 seems most likely, allowing time for Remus to have been infected and his future discussed, whilst having Tom only twenty-six or twenty-seven when Harry saw him and thought of him as a young man.
So what happened about the Transfiguration post, if Minerva started working at Hogwarts in 1956 but Albus didn't become Headmaster until 1964? The fact that Tom Riddle turns up at Hogwarts soon after Albus's promotion, applying for the Defence Against the Dark Arts post, suggests that he knew the DADA post to be vacant - which in turn suggests that Albus had been teaching DADA before that point.
The discussion group on Loose Canon came up with two alternative scenarios.
One: The DADA post became vacant in 1945 when Galatea Merrythought retired. Tom Riddle applied for the job but was turned down by Headmaster Dippet because he was too young. In order to keep Tom from applying again Albus Dumbledore took the DADA job himself, playing on his credentials as the recent vanquisher of Grindelwald. An unnamed person took over as Transfiguration teacher and remained until 1956, when they left for reasons which are not specified, and Minerva McGonagall then took the Transfiguration post.
Two: The DADA post was supposed to became vacant in 1945 when Galatea Merrythought retired. Tom Riddle applied for the job but was turned down by Headmaster Dippet because he was too young. Either Professor Merrythought changed her[?] mind and stayed on (after all we know there were rumours of Merrythought retiring while Tom was in his mid teens, and yet she was still there when Tom finished school at eighteen), or an unknown person took over the DADA job. In 1956, either the unknown person or Professor Merrythought left. That left the DADA post vacant. Albus Dumbledore was concerned that if Tom Riddle were to apply for the DADA post now he would be given it, since he was now almost thirty, so instead he stepped in and took the DADA job himself, playing the "vanquisher of Grindelwald" card. That left the Transfiguration post vacant so Minerva McGonagall was hired.
In both cases, Albus's promotion to Headmaster in circa 1964 left the DADA post vacant, and Tom then applied for it (and cursed it, when he was unsuccessful).