Some of this will be highly speculative, but I will try to justify speculation with canon as much as possible. There will also be plenty of open questions. The goal is to fill in the missing years, between the moment Albus parted ways with Gellert in the summer of 1899 and the moment we see him going to meet Tom Riddle at the orphanage in 1938.
The biggest question I have is about the influence Albus Dumbledore had on headmaster Armando Dippet. We see that in the 1940s Albus had significant influence on the headmaster - he convinced him to remove certain Dark Årts books from the library and to not hire recent alumnus Tom Riddle when veteran DADA prof Merrythought retired. What I find curious in the situation is that Armando listened to Albus' views regarding Dark Arts when Albus was the Transfiguration teacher, while the school had a professor who was a specialist in DADA - above mentioned Galatea Merrythought - who was senior enough to have taught Albus himself back in the day. It would be as if Albus as headmaster preferred the opinions of Severus on the Charms curriculum over those of Filius. How did that come to be?
We don't know what Albus did after his sister's death in August 1899, nor do we know when he started teaching, except it was well before 1938. I'm guessing Albus' time as alchemist under Nikolas Flamel's mentorship took place in the early part of those years. I doubt he had time to do alchemy seriously while teaching a required subject! We don't know anything about Potterverse alchemy except for the fact that Flamel created a working Philosophers' Stone, but if there too alchemy requires a high level of purity from the practitioner then perhaps Albus' reputation as alchemist contributed to him being perceived as an authority in opposing Dark magic? (I wonder if Albus ever confessed - knowingly or unknowingly, willingly or due to some influence - his planned adventures with Gellert to his mentor. Perhaps that was the reason he was called to solve the Dark Lord problem in Europe - because Flamel knew about their shared past and expected some emotional reaction from Gellert.)
But then, if his reputation was in alchemy - and Potions (uses of dragon blood?) - why was he hired as Transfiguration prof? Note that Molly says in HBP that Albus and Horace started teaching at the same time. This sounds like both the Transfiguration and the Potions posts were available. Why not hire the brilliant new teacher for the job that most suited his recent experience? As far as one can tell from canon Albus doesn't claim any public achievements in Transfiguration since those prizes he earned at school. Does this mean that whoever hired him (whether Phineas Nigellus Black or Armando Dippet) had known him in his student days?
So when were Albus and Horace hired? And by whom? Does Molly know of the beginnings of their respective careers because she heard from Muriel, who attended Hogwarts from 1902 to 1909? Or perhaps from her grandparents, who may have attended in the second decade of the 20th century? In that case they were hired by Headmaster Black and started teaching as Armando Dippet's peers. Alternatively they may have been originally hired by Dippet. And depending on what Dippet himself taught, maybe they were hired in 1925 when Dippet became headmaster, with one of them taking Armando's former job. Any indications as to what he might have taught?
But maybe this is the wrong question to ask. If Albus was working with Nikolas, why did he switch to teaching? I seriously doubt canon!Albus would prefer teaching to research, unless something came up that made the research situation unpleasant. Like a reminder that he really shouldn't be involved with this kind of thing that may lead to immortality (of sorts). In the form of news of Gellert's rise in Europe.
So this is my proposed scenario: September 1899, after Aberforth went to Hogwarts for his 5th year, Albus became an apprentice with Nikolas Flamel. They worked on assorted projects. Then news started coming from Europe about what Gellert was up to. At some point, whether because Flamel started hinting that Albus might be able to do something about Gellert or because Albus was becoming uncomfortable with the news and what it implied about his own past, he went to interview for the next teaching job that opened. We don't know when this was because it isn't clear how long it took from the moment Gellert stole the Elder Wand from Gregorovitch until his exploits became newsworthy. Though canon suggests enough time went by for Gellert's appearance to have changed beyond recognition as neither Gregorovitch nor Tom make the connection (is this a theme with Dark Lords?). But this could still have happened while Phineas Nigellus Black was headmaster (say in the early 1920s; 1923 if we want any kind of equivalence with Hitler's timeline). Albus arrived at the school with a reputation as an alchemist. This got him the admiration and following of some teachers, in particular those who were personally or politically uncomfortable with the Dark Arts. While Phineas was still headmaster there was little Albus could do besides networking (besides, he was the new guy around), but once Armando took Phineas' place (presumably in 1925) the time was ripe for Albus to collect the rewards in the form of influencing the new headmaster's policies. And perhaps it was a gradual process, because Merrythought stayed around for 20 more years, so I don't think she wasn't feeling abruptly sidelined.
Somewhere during these years Albus was offered the Ministry - twice, as Tom remembers. I'm guessing the third time was during Tom's absence, which is why he wasn't aware of it when he met Albus again. The Albus of King's Cross exaggerates this number - I think he was trying to impress Harry with how much he believed himself undeserving of power (protesting too much). Of course in the long term he had more influence putting down the Dark Arts at school than by running the Ministry for a decade or so. I tend to think the offer of the
political position came from those who ended up being Dumbledore's supporters in the Wizengamot for decades to come, people like Griselda Marchbanks and Tiberius Ogden. Their support must have been based on his various magical achievements, maybe also the recommendations of Albus' various correspondents. The fact that he had worked with Flamel must have been significant regardless of whether the latter was directly involved. And starting from 1940 these people also called him to take on Gellert. Of course, the two may have been connected - maybe the line was 'if you take care of the European Dark Lord we'll make you Minister'. Or perhaps 'look how we trust you - we want you as Minister! Just go and finish of Grindelwald (before he starts causing trouble here too)'.
Of course in 1945 Albus became the hero of the day and got his own chocolate frog card. From then on for 50 years he got everything he wanted, including controlling any powerful position he could use long term and the upbringing of 2-3 generations of British wizards.
Who else taught at Hogwarts during those years:
Phineas Nigellus Black: Born 1847. Died 1925. I'm guessing he was headmaster until his death. We don't know when he started teaching (but we do know he taught at some point, and loathed interacting with students), nor do we know what he taught nor when he was promoted to headship. Slytherin. We do not know if he was Head of House at some point either. He probably was headmaster when Albus was a student, or at least in Albus' later years as a student.
Galatea Merrythought: Taught DADA from 1895 to 1945. Which means she taught Albus from 4th year on. (Following Terri's proposal that in the past Hogwarts actually taught Dark Arts the transition, if there was one, happened during her tenure. Certainly Horace asks Tom if his interest in Horcruxes was for a project in Defense Against the Dark Arts.) If Phineas taught (DA)DA then maybe she was hired to replace him when he became headmaster.
Armando Dippet - Hogwarts headmaster, probably from 1925 until his death - either in December 1956 or a winter a few years later. It isn't clear what he did before that. Was he a teacher? For how long? What did he teach?
Herbert Beery - taught Herbology when Albus was a young(ish) teacher. Aspiring thespian.
Kettleburn - Care of Magical Creatures. Ended up retiring in 1993. Lost several limbs over his career. The description in 'Tales of Beedle the Bard' makes him appear to have no more common sense than Hagrid wrt the various creatures, but at least he took the risks himself.
Horace Slughorn - taught Potions. Started around the same time Albus did, but was younger (by how much?). Retired in 1981. At some point (before 1940s) became Head of Slytherin. Also founded The Slug Club - an in-House cross-generational networking system.
Someone I believe did not yet teach in those days is Binns. At least not in his ghost form. We know Harry studied from Bathilda Bagshot's textbook, which was published din 1947. This means that as late as 1947 there was a history teacher at Hogwarts who was aware enough of his surroundings to know a new book was published which would suit the curriculum better. Of course this implies that Tom Riddle had a live history teacher who was more involved in teaching than what we see in Harry's days. And puts most of the responsibility for ruining the teaching of history on Albus as headmaster.
The biggest question I have is about the influence Albus Dumbledore had on headmaster Armando Dippet. We see that in the 1940s Albus had significant influence on the headmaster - he convinced him to remove certain Dark Årts books from the library and to not hire recent alumnus Tom Riddle when veteran DADA prof Merrythought retired. What I find curious in the situation is that Armando listened to Albus' views regarding Dark Arts when Albus was the Transfiguration teacher, while the school had a professor who was a specialist in DADA - above mentioned Galatea Merrythought - who was senior enough to have taught Albus himself back in the day. It would be as if Albus as headmaster preferred the opinions of Severus on the Charms curriculum over those of Filius. How did that come to be?
We don't know what Albus did after his sister's death in August 1899, nor do we know when he started teaching, except it was well before 1938. I'm guessing Albus' time as alchemist under Nikolas Flamel's mentorship took place in the early part of those years. I doubt he had time to do alchemy seriously while teaching a required subject! We don't know anything about Potterverse alchemy except for the fact that Flamel created a working Philosophers' Stone, but if there too alchemy requires a high level of purity from the practitioner then perhaps Albus' reputation as alchemist contributed to him being perceived as an authority in opposing Dark magic? (I wonder if Albus ever confessed - knowingly or unknowingly, willingly or due to some influence - his planned adventures with Gellert to his mentor. Perhaps that was the reason he was called to solve the Dark Lord problem in Europe - because Flamel knew about their shared past and expected some emotional reaction from Gellert.)
But then, if his reputation was in alchemy - and Potions (uses of dragon blood?) - why was he hired as Transfiguration prof? Note that Molly says in HBP that Albus and Horace started teaching at the same time. This sounds like both the Transfiguration and the Potions posts were available. Why not hire the brilliant new teacher for the job that most suited his recent experience? As far as one can tell from canon Albus doesn't claim any public achievements in Transfiguration since those prizes he earned at school. Does this mean that whoever hired him (whether Phineas Nigellus Black or Armando Dippet) had known him in his student days?
So when were Albus and Horace hired? And by whom? Does Molly know of the beginnings of their respective careers because she heard from Muriel, who attended Hogwarts from 1902 to 1909? Or perhaps from her grandparents, who may have attended in the second decade of the 20th century? In that case they were hired by Headmaster Black and started teaching as Armando Dippet's peers. Alternatively they may have been originally hired by Dippet. And depending on what Dippet himself taught, maybe they were hired in 1925 when Dippet became headmaster, with one of them taking Armando's former job. Any indications as to what he might have taught?
But maybe this is the wrong question to ask. If Albus was working with Nikolas, why did he switch to teaching? I seriously doubt canon!Albus would prefer teaching to research, unless something came up that made the research situation unpleasant. Like a reminder that he really shouldn't be involved with this kind of thing that may lead to immortality (of sorts). In the form of news of Gellert's rise in Europe.
So this is my proposed scenario: September 1899, after Aberforth went to Hogwarts for his 5th year, Albus became an apprentice with Nikolas Flamel. They worked on assorted projects. Then news started coming from Europe about what Gellert was up to. At some point, whether because Flamel started hinting that Albus might be able to do something about Gellert or because Albus was becoming uncomfortable with the news and what it implied about his own past, he went to interview for the next teaching job that opened. We don't know when this was because it isn't clear how long it took from the moment Gellert stole the Elder Wand from Gregorovitch until his exploits became newsworthy. Though canon suggests enough time went by for Gellert's appearance to have changed beyond recognition as neither Gregorovitch nor Tom make the connection (is this a theme with Dark Lords?). But this could still have happened while Phineas Nigellus Black was headmaster (say in the early 1920s; 1923 if we want any kind of equivalence with Hitler's timeline). Albus arrived at the school with a reputation as an alchemist. This got him the admiration and following of some teachers, in particular those who were personally or politically uncomfortable with the Dark Arts. While Phineas was still headmaster there was little Albus could do besides networking (besides, he was the new guy around), but once Armando took Phineas' place (presumably in 1925) the time was ripe for Albus to collect the rewards in the form of influencing the new headmaster's policies. And perhaps it was a gradual process, because Merrythought stayed around for 20 more years, so I don't think she wasn't feeling abruptly sidelined.
Somewhere during these years Albus was offered the Ministry - twice, as Tom remembers. I'm guessing the third time was during Tom's absence, which is why he wasn't aware of it when he met Albus again. The Albus of King's Cross exaggerates this number - I think he was trying to impress Harry with how much he believed himself undeserving of power (protesting too much). Of course in the long term he had more influence putting down the Dark Arts at school than by running the Ministry for a decade or so. I tend to think the offer of the
political position came from those who ended up being Dumbledore's supporters in the Wizengamot for decades to come, people like Griselda Marchbanks and Tiberius Ogden. Their support must have been based on his various magical achievements, maybe also the recommendations of Albus' various correspondents. The fact that he had worked with Flamel must have been significant regardless of whether the latter was directly involved. And starting from 1940 these people also called him to take on Gellert. Of course, the two may have been connected - maybe the line was 'if you take care of the European Dark Lord we'll make you Minister'. Or perhaps 'look how we trust you - we want you as Minister! Just go and finish of Grindelwald (before he starts causing trouble here too)'.
Of course in 1945 Albus became the hero of the day and got his own chocolate frog card. From then on for 50 years he got everything he wanted, including controlling any powerful position he could use long term and the upbringing of 2-3 generations of British wizards.
Who else taught at Hogwarts during those years:
Phineas Nigellus Black: Born 1847. Died 1925. I'm guessing he was headmaster until his death. We don't know when he started teaching (but we do know he taught at some point, and loathed interacting with students), nor do we know what he taught nor when he was promoted to headship. Slytherin. We do not know if he was Head of House at some point either. He probably was headmaster when Albus was a student, or at least in Albus' later years as a student.
Galatea Merrythought: Taught DADA from 1895 to 1945. Which means she taught Albus from 4th year on. (Following Terri's proposal that in the past Hogwarts actually taught Dark Arts the transition, if there was one, happened during her tenure. Certainly Horace asks Tom if his interest in Horcruxes was for a project in Defense Against the Dark Arts.) If Phineas taught (DA)DA then maybe she was hired to replace him when he became headmaster.
Armando Dippet - Hogwarts headmaster, probably from 1925 until his death - either in December 1956 or a winter a few years later. It isn't clear what he did before that. Was he a teacher? For how long? What did he teach?
Herbert Beery - taught Herbology when Albus was a young(ish) teacher. Aspiring thespian.
Kettleburn - Care of Magical Creatures. Ended up retiring in 1993. Lost several limbs over his career. The description in 'Tales of Beedle the Bard' makes him appear to have no more common sense than Hagrid wrt the various creatures, but at least he took the risks himself.
Horace Slughorn - taught Potions. Started around the same time Albus did, but was younger (by how much?). Retired in 1981. At some point (before 1940s) became Head of Slytherin. Also founded The Slug Club - an in-House cross-generational networking system.
Someone I believe did not yet teach in those days is Binns. At least not in his ghost form. We know Harry studied from Bathilda Bagshot's textbook, which was published din 1947. This means that as late as 1947 there was a history teacher at Hogwarts who was aware enough of his surroundings to know a new book was published which would suit the curriculum better. Of course this implies that Tom Riddle had a live history teacher who was more involved in teaching than what we see in Harry's days. And puts most of the responsibility for ruining the teaching of history on Albus as headmaster.
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