In 289 AC, after Balon's Rebellion was smashed. There was a great tourney thrown at Lannisport. At this tourney, Leyton Hightower made a questionable decision to give his daughter's hand to Ser Jorah Mormont and then disappeared to the clouds (The Hightower), where he has been ever since. In this post I am going to argue that Leyton and/or his daughter Malora (the Mad Maid) made a similar decision to a young girl 13 years before who wanted to see the future...

A Visit to the Maegi's Tent: Leyton Hightower & the Tourney at Lannisport

Background

Even though Jorah proved himself full of valor on Pyke (second behind fearless Thoros and his flaming sword, over the wall) and in the lists at the Tourney at Lannisport (289) where he won and name Lynesse Hightower the Queen of Love and Beauty, there should have been no way that Leyton should have agreed to the match.

Leyton Hightower is Lord of Oldtown, aka the Old Man of Oldtown, aka the Beacon of the South, aka the Defender of Oldtown, aka the Defender of the Citadel, aka the Lord of the Hightower, aka the Lord of the port and aka the Voice Oldtown.. a man with that many titles isn't marrying his daughter to some northern lord (different religions, etc.) on a much lower social scale than him.

Unless...

Something happened that made him do it, something that also has him atop the Hightower for over a decade:

And beyond, where the Honeywine widened into Whispering Sound, rose the Hightower, its beacon fires bright against the dawn. From where it stood atop the bluffs of Battle Island, its shadow cut the city like a sword. Those born and raised in Oldtown could tell the time of day by where that shadow fell. Some claimed a man could see all the way to the Wall from the top. Perhaps that was why Lord Leyton had not made the descent in more than a decade, preferring to rule his city from the clouds. -AFFC, Prologue

and:

Lord Leyton's locked atop his tower with the Mad Maid, consulting books of spells. Might be he'll raise an army from the deeps.

So if you're still following me, Leyton has a)made a very questionable marriage decision and b)disappeared

13 Years Earlier on those same tourney grounds...

When Cersei and friends visit Maggy the Frog at the Tourney for Viserys' birth (276)

The crone's tent was dark, with a tall peaked roof. She did not want to go in, no more than she had wanted to at ten, but the other girls were watching her, so she could not turn away. They were three in the dream, as they had been in life. Fat Jeyne Farman hung back as she always did. It was a wonder she had come this far. Melara Hetherspoon was bolder, older, and prettier, in a freckly sort of way. Wrapped in roughspun cloaks with their hoods pulled up, the three of them had stolen from their beds and crossed the tourney grounds to seek the sorceress. Melara had heard the serving girls whispering how she could curse a man or make him fall in love, summon demons and foretell the future. -AFFC, Cersei VII

So in order for this theory to be true we would need:

• Maggy to still be alive 13 years later (she seems super old in 276, but hey she's "magical")
• Leyton/Malora to have a reason to go to Maggy/believe Maggy

For the sake of this theory Let's assume that hey this old woman is magical so she survived:

The old woman's eyes were yellow, and crusted all about with something vile. In Lannisport it was said that she had been young and beautiful when her husband had brought her back from the east with a load of spices, but age and evil had left their marks on her. She was short, squat, and warty, with pebbly greenish jowls. Her teeth were gone and her dugs hung down to her knees. You could smell sickness on her if you stood too close, and when she spoke her breath was strange and strong and foul

But I readily admit she could have died (or not):

A frightening old crone, supposed to be a priestess. Maegi, they called her. ... He shrugged. "She's long dead, to be sure. And Jeyne seemed a sweet child, I'll grant you, though I only saw her once. But with such doubtful blood . . ." -ASOS, Tyrion III

Leyton/Malora's interest

It should be noted that Maggy was well known in the area.

A frightening old crone, supposed to be a priestess. Maegi, they called her. No one could pronounce her real name. Half of Lannisport used to go to her for cures and love potions and the like.". . ." -ASOS, Tyrion III

and the Hightowers are known to "dabble in the higher mysteries"

The Hightowers were instrumental in the founding of the Citadel and continue to protect it to this day. Subtle and sophisticated, they have always been great patrons of learning and the Faith, and it is said that certain of them have also dabbled in alchemy, necromancy, and other sorcerous arts. -AFFC, Appendix

I am also assuming you also don't get the moniker, "The Mad Maid" for your piety.

So there is no real evidence for this outside of the fact that it would have been in the exact location, the characters had an interest in the arcane and Leyton's "questionable actions" afterwards.

But let's say the maegi saw their futures as well and gave them prophecies? For instance:

she could curse a man or make him fall in love, summon demons and foretell the future. -AFFC, Cersei VII

and:

In a fit of madness, I begged her favor to wear in the tourney, never dreaming she would grant my request, yet she did."

"I fight as well as any man, Khaleesi, but I have never been a tourney knight. Yet with Lynesse's favor knotted round my arm, I was a different man. I won joust after joust. Lord Jason Mallister fell before me, and Bronze Yohn Royce. Ser Ryman Frey, his brother Ser Hosteen, Lord Whent, Strongboar, even Ser Boros Blount of the Kingsguard, I unhorsed them all. In the last match, I broke nine lances against Jaime Lannister to no result, and King Robert gave me the champion's laurel. I crowned Lynesse queen of love and beauty, and that very night went to her father and asked for her hand. I was drunk, as much on glory as on wine. By rights I should have gotten a contemptuous refusal, but Lord Leyton accepted my offer. -ACOK, Daenerys I

or

Lord Leyton's locked atop his tower with the Mad Maid, consulting books of spells. Might be he'll raise an army from the deeps.

Maybe it was just Malora who went and saw the maegi (in a similar situation to what Cersei did earlier, but Malora is likely older) and just went and saw a Woods Witches of Ice and Fire.

But I think its quite likely that Leyton has a glass candle currently and that Maggy's prophecy/vision wa something that a)caused him to marry his daughter to Jorah and b)head to the top of the hightower to consult spells use a glass candle with Malora

If interested: The Man in the High Castle

There is no real evidence for this. Everything is circumstantial. But it does fit as long as the maegi didn't die before 289.

Fun fact: I originally tried typing this up in a replica version where Malora, Lynesse Hightower went to Maggy's tent just like Cersei and friends, with each attendee getting something from that above quote "Lynesse = love, Malora = summon, etc.) but it got too fantastical and didn't really work, so I just decided to lay a base theory (since there really isn't much evidence to begin with).

Fun fact II: Using her siblings ages as frames of reference (and her placement in the order of the AFFC, Appendix), its likely that Malora is the same age as Cersei/Melara.

TLDR: Leyton Hightower and/or Malora the Mad Maid went to Maggy the Frog during the Tourney at Lannisport and learned something that led to the Jorah/Lynesse match and Leyton's stay atop the Hightower for the last decade.