I've just seen an advert for the Harry Potter boxset, and one of the soundbites that stood out to me was when olivander first sees Harry and gives him his wand.
I've been expecting you Harry.
Considering the connection between the two wands (Harry's and Voldemort's), how much of the saga could Olivander have anticipated?
I'm working from when Olivander made the wand, or at least sold it to Riddle, in either the book or film.
I'm not sure if you're asking whether he anticipated when Harry picked the wand, or when he was making the wand?
The answer is "None in great detail", and "None whatsoever", respectively. Let's explore:
Did Olivander plan for Harry to end up with the wand with the twin core? Absolutely not.
First off Olivander tried out several other wands for Harry before giving him the Riddle-paired one. He did not intend to have the Voldemort's wand's twin core wand to be made "specially for Harry", well in advance.
"That will do," he said, and the tape measure crumpled into a heap on the floor. "Right then, Mr. Potter. Try this one. Beechwood and dragon heartstring. Nine inches. Nice and flexible. just take it and give it a wave."
Harry took the wand and (feeling foolish) waved it around a bit, but Mr. Ollivander snatched it out of his hand almost at once.
"Maple and phoenix feather. Seven inches. Quite whippy. Try --"
Harry tried -- but he had hardly raised the wand when it, too, was snatched back by Mr. Ollivander.
"No, no -here, ebony and unicorn hair, eight and a half inches, springy. Go on, go on, try it out."
Harry tried. And tried. He had no idea what Mr. Ollivander was waiting for. The pile of tried wands was mounting higher and higher on the spindly chair, but the more wands Mr. Ollivander pulled from the shelves, the happier he seemed to become.
"Tricky customer, eh? Not to worry, we'll find the perfect match here somewhere -- I wonder, now - - yes, why not -- unusual combination -- holly and phoenix feather, eleven inches, nice and supple."
Notice how he tried different wands, some with phoenix feathers from - presumably - other phoenixes, before getting Harry the paired one.
He was also very surprised when Harry ended up with the wand he did:
Mr. Ollivander cried, "Oh, bravo! Yes, indeed, oh, very good. Well, well, well... how curious... how very curious... "
Now, he DID anticipate seeing Harry, but only because he knew what age The Boy Who Lived was:
"Ah yes," said the man. "Yes, yes. I thought I'd be seeing you soon. Harry Potter." It wasn't a question. "You have your mother's eyes. It seems only yesterday she was in here herself, buying her first wand. Ten and a quarter inches long, swishy, made of willow. Nice wand for charm work."
Did Olivander anticipate details of the subsequent saga when Harry was chosen by the twin core wand?
Not in great detail, but he obviously had anticipation that something will happen
He was clearly interested in Harry, Voldemort and the whole story:
"I'm sorry to say I sold the wand that did it," he said softly. "Thirteen-and-a-half inches. Yew. Powerful wand, very powerful, and in the wrong hands... well, if I'd known what that wand was going out into the world to do...."
Again, see that he didn't anticipate anything special when he paired Tom Riddle with his wand either, beforehand.
BUT, he did know there was some special magic at work due to the paired cores, and was clearly anticipating for something to happen out of the ordinary (just not the specifics):
Mr. Ollivander cried, "Oh, bravo! Yes, indeed, oh, very good. Well, well, well... how curious... how very curious... "
He put Harry's wand back into its box and wrapped it in brown paper, still muttering, "Curious... curious..
"Sorry," said Harry, "but what's curious?"
Mr. Ollivander fixed Harry with his pale stare.
"I remember every wand I've ever sold, Mr. Potter. Every single wand. It so happens that the phoenix whose tail feather is in your wand, gave another feather -- just one other. It is very curious indeed that you should be destined for this wand when its brother why, its brother gave you that scar."
Harry swallowed.
"Yes, thirteen-and-a-half inches. Yew. Curious indeed how these things happen. The wand chooses the wizard, remember.... I think we must expect great things from you, Mr. Potter.... After all, He-Who-Must-Not-Be-Named did great things -- terrible, yes, but great."
Yes, Olivander anticipated great things. But he clearly didn't anticipate anything specific aside from the fact that it would be great.
I think mostly not, for two main reasons.
First, Ollivander implies if he had known what Voldemort's yew wand was going to do (i.e. murders, dark magic, create The Boy Who Lived) he might have done something differently (he doesn't specify what).
Mr Ollivander touched the lightning scar on Harry’s forehead with a long, white finger.
‘I’m sorry to say I sold the wand that did it,’ he said softly. ‘Thirteen and a half inches. Yew. Powerful wand, very powerful, and in the wrong hands ... Well, if I’d known what that wand was going out into the world to do ...’
Philosopher's Stone - page 64 - Bloomsbury - chapter 5, Diagon Alley
Dumbledore himself admits when he first met Voldemort he did not suspect that eleven-year-old Tom Riddle would go on to become the most dangerous dark wizard in history, although he found Tom Riddle odd and entitled, and enough of a gut feeling to keep a close eye on Tom while he was a student at Hogwarts. If Dumbledore couldn't put his finger on exactly what would happen between Tom Riddle/Voldemort and Harry Potter at the time(s) that the twin core wands were created (which canon doesn't address), I don't expect Ollivander would have been able to.
The second and more important reason, I think, is that there was absolutely no connection between Harry and Voldemort until Voldemort took stock in Sybill Trelawney's prophecy and marked Harry as his equal. The prophecy is only authoritative because Voldemort chooses to make it so. He continues to do so throughout the series because he doesn't know the whole prophecy, as Snape, while spying on Dumbledore and Trewlawney as a Death Eater, only overheard part of it and misreported the prophecy's predictions to Voldemort.
If I recall correctly, the only individuals who knew what the full prophecy said by the time we get to Half-Blood Prince are Dumbledore and Harry. Later, Harry tells Ron and Hermione about the prophecy, at Dumbledore's prompting (Half-Blood Prince - chapter 4 - Horace Slughorn) .
This happened after at least one of the Phoenix feather wands had been made -- Voldemort's yew wand. Tom Riddle was a first year at Hogwarts around 1936-1937. Harry wasn't born until 1980. And we have no idea when Harry's wand was actually made. So, I err on the side of Ollivander not knowing exactly what might happen between Voldemort's and Harry's wands.
That said, undoubtedly Ollivander, arguably the most skilled and intuitive wandmaker in the Wizarding world, would know that wands with twin cores are capable of Priori Incantatem. So, Ollivander remembering every wand he's ever sold, might have been able to know at the moment both wands were made and in existence, that if they met in a duel, Priori Incantatem would be possible. Ollivander knew that Voldemort had the yew wand and that Harry had the holly wand, and he knew about the twin cores, so it's clear he would have been able to know about the possibility (however remote) of Priori Incantatem, which did indeed occur between Harry and Voldemort in Goblet of Fire.
