Illyrio’s Plan

(Top image: Illyrio Mopatis, by Jake Murray @Fantasy Flight Publishing)

“Which plan?” said Tristan Rivers. “The fat man’s plan? The one that changes every time the moon turns?” (aDwD, The Lost Lord)

From the moment that Illyrio appeared discussing war strategies beneath the red keep in aGoT, many have attempted to pinpoint what Varys and Illyrio are hoping to get out of all of their plans, what the motivations of both Varys and Illyrio are. Are they Targaryen loyalists? Or Blackfyres? Is Young Griff just Illyrio’s Valyrian looking son? Did he truly mourn over Viserys’ death? Or did he use reverse psychology on Viserys to get him to join with the Dothraki, knowing it would get him killed? And some suggest that Illyrio just wants to destroy the Iron Bank of Braavos so that Illyrio can become the planet’s moneylender. Are Varys and Illyrio one mind and unit, who have the same exact motivation? Or do they have differring interests?

While not all has been revealed yet, I think the chapter in which Jon Connington introduces Aegon to the Golden Company reveals certain aspects of the plan for us to at least reconstruct the plan as far as Aegon, Viserys and Daenerys goes from the start of the aSoIaF series. Meanwhile the history of Pentos sheds a light on how Illyrio must go about it.

And this essay comes with the warning that I treat the little information we do have on Illyrio’s and Varys’s past at face value. This was an exercise to make sense of Illyrio’s past before aGoT and the series’ timeline into a coherent storyline, character motivation and plan if I assumed that neither Varys or Illyrio are Blackfyre or Targaryen descendants, and that Aegon is indeed Aegon Targaryen. While I do have to fill in some gaps for uncomfirmed necessary data, I find it is possible for Illyrio’s motivation and plan to be consistent within those restrictions. And if the plot (past and present) remains consistent and can hold up without Illyrio being a Blackfyre or Targaryen, without being Aegon’s true father, then it becomes a valid alternative to those secret identity theories.

Aegon and the Golden Company

Tristan Rivers reveals Illyrio’s military plan at the start of the series and how it changed over time, because of circumstances.

“First Viserys Targaryen was to join us with fifty thousand Dothraki screamers at his back. Then the Beggar King was dead, and it was to be the sister, a pliable young child queen who was on her way to Pentos with three new-hatched dragons. Instead the girl turns up on Slaver’s Bay and leaves a string of burning cities in her wake, and the fat man decides we should meet her by Volantis. Now that plan is in ruins as well.” (aDwD, The Lost Lord)

Tristan Rivers confirms that Illyrio did want Viserys to acquire an army of Dothraki, and Viserys was to join the Golden Company with them. Now, I know that the sceptics of the veracity of this rely on several arguments against this. Have some patience though, as I will tackle the “issues”.

And one of the ways I will do this is by stressing Tristan’s wording –  Viserys and the Dothraki were to join the Golden Company, not the other way around. It is a seeming subtle difference, but very important.

The reveal of Jon Connington’s survival to raise Aegon and the blood contract between the Golden Company seems the first huge counter argument against Illyrio desiring Viserys’ survival of his travels with the Dothraki.

“The Golden Company marches toward Volantis as we speak, there to await the coming of our queen out of the east.”
Beneath the gold, the bitter steel. “I had heard the Golden Company was under contract with one of the Free Cities.”
“Myr.” Illyrio smirked. “Contracts can be broken.”
“There is more coin in cheese than I knew,” said Tyrion. “How did you accomplish that?”
The magister waggled his fat fingers. “Some contracts are writ in ink, and some in blood. I say no more.” (aDwD, Tyrion II)

When Tyrion and Illyrio travel through the hinterland of Pentos, the heartland of what once was Andalos, Illyrio reveals that the Golden Company is journeying to Volantis. aFfC already confirmed via Cersei’s chapters that the Golden Company had broken their contract with Myr, which was unheard of (see also Aurane, the Lord of Waters, Part 1 – The Set Up). They never broke a contract in history before (see also House Blackfyre). Illyrio also confirms the news that the Golden Company is marching for Volantis as Qyburn learns and tells at Cersei’s small council.

What we and nobody else knew yet in aFfC was that the Golden Company was moving because of an older contract, not one that was bought and paid for, but bound by blood. While Illyrio makes it appear as if this is purely for Daenerys Targaryen, later on Tyrion uncovers the true intended benefactor: the supposed son of Rhaegar Targaryen, Aegon VI Targaryen, introduced and disguised as Young Griff.

Aegon VI Targaryen, by dani2003kato

“Why,” said Tyrion, “if the stone men had taken Yandry or Griff or our lovely Lemore, we would have grieved for them and gone on. Lose you, and this whole enterprise is undone, and all those years of feverish plotting by the cheesemonger and the eunuch will have been for naught … isn’t that so?” […] “The blue hair makes your eyes seem blue, that’s good. And the tale of how you color it in honor of your dead Tyroshi mother was so touching it almost made me cry. Still, a curious man might wonder why some sellsword’s whelp would need a soiled septa to instruct him in the Faith, or a chainless maester to tutor him in history and tongues. And a clever man might question why your father would engage a hedge knight to train you in arms instead of simply sending you off to apprentice with one of the free companies. It is almost as if someone wanted to keep you hidden whilst still preparing you for … what? Now, there’s a puzzlement, but I’m sure that in time it will come to me. I must admit, you have noble features for a dead boy.” […] “Men will tell you that I am a kingslayer, a kinslayer, and a liar, and all of that is true … but then, we are a company of liars, are we not? Take your feigned father. Griff, is it?” The dwarf sniggered. “You should thank the gods that Varys the Spider is a part of this plot of yours. Griff would not have fooled the cockless wonder for an instant, no more than it did me. No lord, my lordship says, no knight. And I’m no dwarf. Just saying a thing does not make it true. Who better to raise Prince Rhaegar’s infant son than Prince Rhaegar’s dear friend Jon Connington, once Lord of Griffin’s Roost and Hand of the King?” (aDwD, Tyrion V)

After Jon’s failure to capture and kill Robert Baratheon at Stoney Sept during Robert’s Rebellion, the Mad King stripped him from his position as Hand, stripped him of his lands and exiled him. In Essos, JonCon joined the Golden Company under the command of Myles Toyne (283 AC) and rose to high ranks in the next five years. Then in 288 AC, the war chest of the Golden Company was stolen and Jon Connington took the blame for it and pretended to have died drinking himself to death in Lys.

Jon Connington might have been one of those successors [of Aegor Rivers] if his exile had gone otherwise. He had spent five years with the company, rising from the ranks to a place of honor at Toyne’s right hand. Had he stayed, it might well have been him the men turned to after Myles died, instead of Harry Strickland. But Griff did not regret the path he’d chosen. (aDwD, The Lost Lord)

Griff wondered how many of them knew who he was. Few enough. Twelve years is a long time. […] So far as most of them were concerned, Connington had drunk himself to death in Lys after being driven from the company in disgrace for stealing from the war chest. The shame of the lie still stuck in his craw, but Varys had insisted it was necessary. “We want no songs about the gallant exile,” the eunuch had tittered, in that mincing voice of his. “Those who die heroic deaths are long remembered, thieves and drunks and cravens soon forgotten.” […] Griff had gone along with the Spider’s scheme for the boy’s sake, but that did not mean he liked it any better. (aDwD, The Lost Lord)

This was Varys’s planned cover story concocted together with Ser Myles Toyne to have Jon Connington raise, tutor and train Aegon in deep secret.

Does [Harry Strickland] know? Griff wondered. How much did Myles tell him? Varys had been adamant about the need for secrecy. The plans that he and Illyrio had made with Blackheart had been known to them alone. The rest of the company had been left ignorant. What they did not know they could not let slip. (aDwD, The Lost Lord)

Varys and Illyrio knew they could trust Jon Connington, because the man not only had been Rhaegar’s best friend. He had been in love with Rhaegar and felt guilty over the crown prince’s demise. And Jon Connington did this for twelve years, before he returned with Aegon to the Golden Company, now led by Harry Strickland in 300 AC.

“Beneath the Gold the Bitter Steel”, by Urukki Saki, depicting the Golden Company and its current prominent members

Anyhow, we can conclude that in 288 AC, Varys recruited Jon Connington to supervise the young prince and made a contract writ in blood with Myles Toyne, the commander of the Golden Company. From the start, the Company was intended to be Aegon’s army, not Viserys’s. Dany remembers that Viserys once attempted to recruit the Golden Company.

Her brother Viserys had once feasted the captains of the Golden Company, in hopes they might take up his cause. They ate his food and heard his pleas and laughed at him. Dany had only been a little girl, but she remembered. (aDwD, Daenerys III)

In 297 AC, Dany is thirteen and had her moon cycles in order for her to be wed to Khal Drogo. By then she has lived almost half a year at Illyrio’s mansion, who took her and Viserys in. For her to be a little girl when Viserys feasted the Golden Company to take up Viserys III Targaryen’s cause, this must have occurred before Myles Toyne’s death in 296 AC. Meanwhile, this must have happened after they were driven out of Braavos. Willem Darry fell ill, when Dany was five, and slowly wasted away. Since, Dany was born in 284 AC, Viserys and her left Braavos after 289 AC. So, the contract with the Golden Company between Varys, Illyrio and Myles Toynce was already agreed to.

It would have been unlikely that Viserys would have even managed to get an audience with the Golden Company, before he reached adulthood (sixteen). Viserys was born 276 AC, so this feasting of the captains of the Golden Company would have happened between 292 AC and (early) 296 AC, or when Dany was between 8 to 11 years old.

So, when Jon Connington refers to the Golden Company as Aegon’s army, then this very much was the case.

Griff would be glad to go back to his own true colors too, though his once red hair had gone to grey. He clapped the lad on the shoulder. “Shall we go? Your army awaits your coming.”
“I like the sound of that. My army.” A smile flashed across his face, then vanished. “Are they, though? They’re sellswords. Yollo warned me to trust no one.”
“There is wisdom in that,” Griff admitted. It might have been different if Blackheart still commanded, but Myles Toyne was four years dead, and Homeless Harry Strickland was a different sort of man. (aDwD, The Lost Lord)

Aegon would have been between 10 or 14 at the time of Viserys’ meeting with Myles Toyne. On top of that Robert’s alliance with the Vale, Westerlands and the North was still too strong. Westeros was united behind Robert I Baratheon after the Greyjoy’s Rebellion of 289 AC, and his queen Cersei had given him three children. If the Golden Company’s contract was tied to Aegon Targaryen, and not the Targaryens as a whole, then Illyrio and Varys would have wanted to wait for the Golden Company to go public at least until Aegon would be considered an adult in the eyes of Westeros. So, not before 298 AC. That timing fits perfectly with Illyrio having arranged for Dany to be wed to Viserys, and set their war plans in motion for Viserys to acquire an army of Dothraki screamers.

Viserys III or Daenerys Targaryen

So, why am I certain that Illyrio wanted Viserys to join Aegon’s Company? Harry Strickland spells it out, when Franklyn Flowers expresses eagerness to agree to Aegon’s plan to sail for Westeros without Dany.

The captain-general looked as if someone had slapped his face. “Has the sun curdled your brains, Flowers? We need the girl. We need the marriage. If Daenerys accepts our princeling and takes him for her consort, the Seven Kingdoms will do the same. Without her, the lords will only mock his claim and brand him a fraud and a pretender. (aDwD, The Lost Lord)

Real or fake, Aegon Targaryen’s “death” was so legendary and well known, that anyone involved in the plot anticipated that lords would rather believe him to be a pretender, over being a true Targaryen. The plotters believed they required at least one undeniable Targaryen to join Aegon’s company to give him the perception of legitimacy. In 300 AC, Illyrio, Jon Connington and Harry Strickland believe Dany to serve that purpose. But by then the plans had altered, because of Viserys’s death. Illyrio’s first plan in 298 AC was for Viserys to extend the Targaryen legitimacy to Aegon. If the exiled king Viserys III Targaryen accepted Young Griff as his surviving nephew and heir, then so would the Seven Kingdoms.

For this legitimacy via Viserys III, Illyrio and Varys needed Viserys and Dany to wander every Free City in Essos for so many years. The Targaryen siblings’ identity and whereabouts needed to be well established and known, so that nobody would ever doubt Viserys’s acceptance of Aegon.

Drogo’s burial, by Magali Villeneuve

That Illyrio intended for Aegon to join the Targaryen claim along with Viserys is further symbolized by the three dragon eggs that Illyrio gifted Dany. In olden days, when dragons still lived, Targaryens were gifted a dragon egg at birth. Illyrio acquired three of such eggs, not one, not two, but three, because he wanted people to believe that there were three Targaryens when they learned of the tale of Dany’s wedding.

Magister Illyrio murmured a command, and four burly slaves hurried forward, bearing between them a great cedar chest bound in bronze. When she opened it, she found piles of the finest velvets and damasks the Free Cities could produce … and resting on top, nestled in the soft cloth, three huge eggs. Dany gasped. They were the most beautiful things she had ever seen, each different than the others, patterned in such rich colors that at first she thought they were crusted with jewels, and so large it took both of her hands to hold one. She lifted it delicately, expecting that it would be made of some fine porcelain or delicate enamel, or even blown glass, but it was much heavier than that, as if it were all of solid stone. The surface of the shell was covered with tiny scales, and as she turned the egg between her fingers, they shimmered like polished metal in the light of the setting sun. One egg was a deep green, with burnished bronze flecks that came and went depending on how Dany turned it. Another was pale cream streaked with gold. The last was black, as black as a midnight sea, yet alive with scarlet ripples and swirls. “What are they?” she asked, her voice hushed and full of wonder.
“Dragon’s eggs, from the Shadow Lands beyond Asshai,” said Magister Illyrio. “The eons have turned them to stone, yet still they burn bright with beauty.” (aGoT, Daenerys II)

A Bride for Dothraki Screamers

Now let us check this with the conversation between Viserys and Illyrio about when he could expect Khal Drogo to gift him an army of Dothraki in return for gifting Dany as bride.

“Best we get Princess Daenerys wedded quickly before they hand half the wealth of Pentos away to sellswords and bravos,” Ser Jorah Mormont jested.
[…]
Magister Illyrio laughed lightly through his forked beard, but Viserys did not so much as smile. “He can have her tomorrow, if he likes,” her brother said. He glanced over at Dany, and she lowered her eyes. “So long as he pays the price.”
Illyrio waved a languid hand in the air, rings glittering on his fat fingers. “I have told you, all is settled. Trust me. The khal has promised you a crown, and you shall have it.”
“Yes, but when?”
“When the khal chooses,” Illyrio said. “He will have the girl first, and after they are wed he must make his procession across the plains and present her to the dosh khaleen at Vaes Dothrak. After that, perhaps. If the omens favor war.”
Viserys seethed with impatience. “I piss on Dothraki omens. The Usurper sits on my father’s throne. How long must I wait?”
Illyrio gave a massive shrug. “You have waited most of your life, great king. What is another few months, another few years?” (aGoT, Daenerys II)

Dany’s wedding has been timelined by fans to have occurred either late 297 AC or early 298 AC, and it took the Dothraki half a year at least to travel to Vaes Dothrak. In other words, Illyrio did not expect or plan for Khal Drogo to return and gift Viserys an army before early 299 AC.

Looking like a princess, “Daenerys Targaryen” by /u/arenzio

To Illyrio, Viserys expresses doubts on whether a man like Drogo would want a “woman” that young. Dany is but thirteen years old when she meets and weds Khal Drogo.

“She is a vision, Your Grace, a vision,” he told her brother. “Drogo will be enraptured.”
“She’s too skinny,” Viserys said. […] He rested his hand on the hilt of the sword that Illyrio had lent him, and said, “Are you sure that Khal Drogo likes his women this young?”
“She has had her blood. She is old enough for the khal,” Illyrio told him, not for the first time. (aGoT, Daenerys I)

Illyrio uses the fact that Dany had started to bleed as reason to arrange the wedding, in the same way that Tywin does later on with Sansa when he weds Sansa to Tyrion. Later on, Illyrio reveals to Tyrion how Viserys intended to steal into Dany’s bedroom the night before her wedding to at least claim her maidenhead, if he could not have her as his sister-wife.

“Dothraki neither buy nor sell. Say rather that her brother Viserys gave her to Drogo to win the khal’s friendship. A vain young man, and greedy. Viserys lusted for his father’s throne, but he lusted for Daenerys too, and was loath to give her up. The night before the princess wed he tried to steal into her bed, insisting that if he could not have her hand, he would claim her maidenhead. Had I not taken the precaution of posting guards upon her door, Viserys might have undone years of planning.” (aDwD, Tyrion II)

If Illyrio planned years ahead, then the above implies, he invited Viserys and Dany to live under his roof from the time Illyrio expected her to bleed for the first time. This gave Illyrio the ability to prevent Viserys or others from wedding or bedding her, and ruin the wedding pact with a man of Illyrio’s choosing. Dany turned thirteen in 297 AC.

This is awfully young and dangerously so, not just in our society, but on Planetos as well. While the bodies of girls this young can show signs of fertility, their bodies are mostly still too undeveloped to either survive child birth or for their body not to suffer permanent damage. That is why when nobles wed a girl as young as Dany, the men are often advized to wait with the consummation of it. The main purpose of similar marriage deals in Westeros is to secure the alliance while preserving the girl’s maidenhead.

Illyrio though never urges Khal Drogo to delay the consummation, not through years of engagement or warning Drogo about the likelihood of Dany dying in child birth. The marriage deal between Viserys and Khal Drogo that Illyrio helped set up proves Illyrio had no concern for Dany’s physical well being, survival, or for her to remain fertile. Illyrio admits to this too.

The fat man grew pensive. “Daenerys was half a child when she came to me, yet fairer even than my second wife, so lovely I was tempted to claim her for myself. Such a fearful, furtive thing, however, I knew I should get no joy from coupling with her. Instead I summoned a bedwarmer and fucked her vigorously until the madness passed. If truth be told, I did not think Daenerys would survive for long amongst the horselords.” (aDwD, Tyrion II)

As soon as Dany was wedded and bedded by the Khal, Illyrio expected Drogo to be bound to keep his promise to gift Viserys his army at some point. That Illyrio saw Dany as no other purpose than to be of use as an expendable bride to form a military alliance is later proven when both Illyrio and Varys risk Dany’s life by setting up an assassination attempt. While they did give Jorah a head’s up over it, he saved Dany only in the nick of time. Now, I do not mean to go as far as to say that Illyrio desired her death throughout aGoT, just that her survival was not crucial for Illyrio’s first plan, as much as her maidenhead was to secure a military alliance with the Dothraki, or a threat to her life was to trigger Khal Drogo into wanting to invade Westeros.

Omens of War

It should also be noted that while Illyrio hosted Viserys and Dany in his home, at the other side of the narrow sea, Jon Arryn had begun to study the breeding of hounds and eventually involved Stannis in visiting Robert’s bastards. Varys was certainly aware that the alliance between Robert Baratheon, Jon Arryn and the Lannisters would crack. If the potboy can gossip about it, then Varys knew it too.

The potboy, now cordwainer, had never exchanged so much as a word with Lord Jon, but he was full of oddments of kitchen gossip: the lord had been quarreling with the king, the lord only picked at his food, the lord was sending his boy to be fostered on Dragonstone, the lord had taken a great interest in the breeding of hunting hounds, the lord had visited a master armorer to commission a new suit of plate, wrought all in pale silver with a blue jasper falcon and a mother-of-pearl moon on the breast. The king’s own brother had gone with him to help choose the design, the potboy said. No, not Lord Renly, the other one, Lord Stannis. (aGoT, Eddard VI)

Varys later confirms to Tyrion that Littlefinger pointed the way to discover the truth about Cersei’s children through Robert’s bastard with Jon Arryn and Stannis, aside from Ned Stark. It was after all Jon Arryn who had raised Littlefinger to the position he was in.

“[Stannis] accuses my brother and sister of incest. I wonder how he came by that suspicion.”
“Perhaps he read a book and looked at the color of a bastard’s hair, as Ned Stark did, and Jon Arryn before him. Or perhaps someone whispered it in his ear.” The eunuch’s laugh was not his usual giggle, but deeper and more throaty.
“Someone like you, perchance?”
“Am I suspected? It was not me.”
“If it had been, would you admit it?”
“No. But why should I betray a secret I have kept so long? It is one thing to deceive a king, and quite another to hide from the cricket in the rushes and the little bird in the chimney. Besides, the bastards were there for all to see.”
[…]
“If you were not this whisperer, who was?”
“Some traitor, doubtless.” Varys tightened the cinch.
“Littlefinger?”
“I named no name.” (aCoK, Tyrion IV)

By Varys-speak that is confirmation that besides Ned Stark, Littlefinger who informed Ned Stark. Furthermore, Stannis regards Varys as the cause of the rot of the Mad King’s reign.

“[…] I mean to scour that court clean. As Robert should have done, after the Trident. Ser Barristan once told me that the rot in King Aerys’s reign began with Varys. The eunuch should never have been pardoned. No more than the Kingslayer.” (aSoS, Davos IV)

This all gives us a better understanding of the conversation between Illyrio and Varys that Arya overhears in the tunnels beneath the red keep.

“The fools tried to kill his son, and what’s worse, they made a mummer’s farce of it. He’s not a man to put that aside. I warn you, the wolf and lion will soon be at each other’s throats, whether we will it or no.”
“Too soon, too soon,” the voice with the accent complained. “What good is war now? We are not ready. Delay.” (aGoT, Arya III)

Illyrio wants Varys to delay the civil war that Varys fears is coming soon.

“What would you have me do?” asked the torchbearer, a stout man in a leather half cape. […]
“If one Hand can die, why not a second?” replied the man with the accent and the forked yellow beard. “You have danced the dance before, my friend.”
[…]
“Before is not now, and this Hand is not the other,” the scarred man said as they stepped out into the hall. (aGoT, Arya III)

Since aDwD, we know that Illyrio was talking of Jon Connington, not Jon Arryn. Neither Varys and Illyrio had anything to do with the death of Jon Arryn. It was Lysa Arryn who poisoned her husband through Littlefinger’s manipulations.

“Perhaps so,” the forked beard replied, pausing to catch his breath after the long climb. “Nonetheless, we must have time. The princess is with child. The khal will not bestir himself until his son is born. You know how they are, these savages.” (aGoT, Arya III)

At the time of this meeting between Illyrio and Varys, Illyrio does not expect Khal Drogo and Viserys to return to Pentos before mid 299 AC. Obviously, in the minds of Varys and Illyrio, if Dany were to die or miscarry before the end of the third trimester, then Drogo could be triggered into acting sooner on behalf of Viserys. So, instead of keeping Dany’s pregnancy a secret, Varys informs Robert and the small council, and he supports a public assassination order that Illyrio would ensure would reach Vaes Dothrak, regardless of Robert’s wishes.

“If he does not bestir himself soon, it may be too late,” the stout man in the steel cap said. “This is no longer a game for two players, if ever it was. […] Delay, you say. Make haste, I reply. Even the finest of jugglers cannot keep a hundred balls in the air forever.” (aGoT, Arya III)

The former potboy mentions a fight between Jon Arryn and Robert Baratheon. It was likely Varys’s news that Illyrio had taken in Viserys and Dany. And Varys would have informed Robert of this at a moment of his own convenience, as we witness when he sent a rider to inform Robert of Dany’s marriage to Khal Drogo.

“Well, I did not bring you out here to talk of graves or bicker about your bastard. There was a rider in the night, from Lord Varys in King’s Landing. Here.” The king pulled a paper from his belt and handed it to Ned. (aGoT, Eddard II)

Here we see the nature of Varys’s game with Robert and the Hand. Since the Spider conspired with Illyrio, he knew very well when Dany would wed Khal Drogo. More, the timeline indicators imply that Dany’s wedding took place well before Robert even left for Winterfell. Varys sat on that info as Robert and the whole royal cart train made its way north, including a stay at House Darry (still secret Targaryen royalists). He sat on it during Robert’s extended stay at Winterfell. He sent a speed courier on horse, when Varys was certain Robert would be on the road south with Ned Stark. He could have sent a raven at any given time, much sooner. Instead, he waited until Robert was like to consult with his new Hand, Ned Stark, without any other voice of the Small Council to influence either two. The rider was a mummer’s farce.

It accomplished several things:

  • Varys appeared to be giving urgent spy information as soon as possible, while he actually delayed to get the news to Robert.
  • He bought time for Dany and the Dothraki to be well out of reach of potential assassins. Around the time that Robert got the news of Dany’s wedding, Dany would have been traversing through the Hills of Norvos or staring at the silver lemures in the forests of Qohor, if she was not already near the edges of the Dothraki Sea.
  • He tested how much Ned Stark was able and still willing to resist Robert’s will to assassinate both Viserys, Dany (and potentially Aegon in the future).

“Ser Jorah is now in Pentos, anxious to earn a royal pardon that would allow him to return from exile,” Robert explained. “Lord Varys makes good use of him.” […] “Varys tells me that spies are more useful than corpses,” Robert said. “Jorah aside, what do you make of his report?”
“Daenerys Targaryen has wed some Dothraki horselord. What of it? Shall we send her a wedding gift?” (aGoT, Eddard II)

The claim that Ser Jorah Mormont is “now” in Pentos is a falsehood: the khalasar broke camp the morning after her wedding and started the long trek to Vaes Dothrak. And as “urgent” Varys made this news appear, it does not appear that Stannis packing up and leaving for Dragonstone altogether was newsworthy. Eddard only discovers this when he arrives in King’s Landing. Lysa Arryn fleeing for the Eyrie is more newsworthy and cause of speculation than the king’s own brother decamping to Dragonstone is.

We witness Robert’s irrational anger over Rhaegar during Ned’s exchange with Robert over this tricky wedding news.

“Nonetheless,” Ned said, “the murder of children … it would be vile … unspeakable …”
“Unspeakable?” the king roared. “What Aerys did to your brother Brandon was unspeakable. The way your lord father died, that was unspeakable. And Rhaegar … how many times do you think he raped your sister? How many hundreds of times?” His voice had grown so loud that his horse whinnied nervously beneath him. The king jerked the reins hard, quieting the animal, and pointed an angry finger at Ned. “I will kill every Targaryen I can get my hands on, until they are as dead as their dragons, and then I will piss on their graves.”
Ned knew better than to defy him when the wrath was on him. (aGoT, Eddard II)

Nothing could rile up Robert as much as the news of either Viserys or Dany. And similar new must have been what caused Robert to roar at Jon Arryn in the weeks or months leading up to Jon Arryn’s death.

“You can’t get your hands on this one, can you?” [Ned] said quietly.
The king’s mouth twisted in a bitter grimace. “No, gods be cursed. Some pox-ridden Pentoshi cheesemonger had her brother and her walled up on his estate with pointy-hatted eunuchs all around them, and now he’s handed them over to the Dothraki. I should have had them both killed years ago, when it was easy to get at them, but Jon was as bad as you. More fool I, I listened to him.” (aGoT, Eddard II)

Most likely, Varys delayed giving the info of Illyrio hosting Viserys and Dany the same way he did with Dany’s wedding, and he would have cited the same source for it – Ser Jorah Mormont. The “spy” does not join Viserys and Dany until they meet with Khal Drogo and the marriage pact is agreed to, nigh half a year since Illyrio took them in. This would have been either late 297 AC or early 298 AC just a few weeks before Jon Arryn’s death.

We can conclude that before Illyrio urges Varys beneath the red keep to delay the foreseeable civil war, Varys had been doing this as much as he could for over a year.

Viserys’s intended survival
Viserys, by Renzo Gonzalez

So, if Dany was expendable, then Viserys was not. I already mentioned that Illyrio and the Golden Company expected Viserys to join Aegon’s Company in order to convince the Lords of Westeros that Aegon’s claim of identity was real. Tristan Rivers’ words  about the fat man’s first plan attest to the intended survival of Viserys. But so does the letter that Illyrio writes that warns Jorah just in the nick of time to save Dany from an assassination.

While most readers remember that Ser Jorah read the letter, most misremember it as being addressed to Jorah Mormont. It was in fact addressed to Viserys.

Under the hollow hummock of earth that was her home in Vaes Dothrak, Dany ordered them to leave her—all but Ser Jorah. “Tell me,” she commanded as she lowered herself onto her cushions. “Was it the Usurper?”
“Yes.” The knight drew out a folded parchment. “A letter to Viserys, from Magister Illyrio. Robert Baratheon offers lands and lordships for your death, or your brother’s.”
“My brother?” Her sob was half a laugh. “He does not know yet, does he? The Usurper owes Drogo a lordship.” This time her laugh was half a sob. She hugged herself protectively. “And me, you said. Only me?”
“You and the child,” Ser Jorah said, grim. (aGoT, Daenerys VI)

Both Robert Baratheon and Illyrio were unaware that Viserys had been crowned and killed by Drogo with molten gold. Jorah read the letter, because Viserys was not alive anymore to pick up the letter or read it himself. That Jorah ended up reading it, does not annull the fact that Illyrio attempted to warn Viserys himself of the risk of assassination. Therefore, Illyrio hoped to prevent at least Viserys from getting killed.

So, when Illyrio argued with Viserys to remain in Pentos and not journey with the khalasar to Vaes Dothrak himself, he was not using reverse psychology. Instead, he did indeed intend to keep Viserys safe in Pentos.

Her brother was miserable out here. He ought never have come. Magister Illyrio had urged him to wait in Pentos, had offered him the hospitality of his manse, but Viserys would have none of it. He would stay with Drogo until the debt had been paid, until he had the crown he had been promised. “And if he tries to cheat me, he will learn to his sorrow what it means to wake the dragon,” Viserys had vowed, laying a hand on his borrowed sword. Illyrio had blinked at that and wished him good fortune. (aGoT, Daenerys III)

Even Ser Jorah attests to this.

The knight looked after Viserys doubtfully. “Your brother should have bided his time in Pentos. There is no place for him in a khalasar. Illyrio tried to warn him.”
“He will go as soon as he has his ten thousand. My lord husband promised a golden crown.”
Ser Jorah grunted. “Yes, Khaleesi, but … the Dothraki look on these things differently than we do in the west. I have told him as much, as Illyrio told him, but your brother does not listen.” (aGoT, Daenerys IV)

So, yes, Illyrio wept tears when he learned of Viserys’s death.

“Magister Illyrio has protected me in the past. Strong Belwas says that he wept when he heard my brother was dead.”
“Yes,” said Mormont, “but did he weep for Viserys, or for the plans he had made with him?” (aSoS, Daenerys I)

And Ser Jorah is correct too that Illyrio wept for how he saw the plan he had been years in the making come to ruins, rather than grieving the death of Viserys as a person or even potential Targaryen king. To Tyrion, Illyrio also admits that he considered Viserys a vain and greedy fool, and very much the Mad King’s son.

“He sounds an utter fool.”
“Viserys was Mad Aerys’s son, just so. Daenerys … Daenerys is quite different.” (aDwD, Tyrion II)

So, why would Illyrio want the legally named heir Viserys III to serve as the badge of credibility for Aegon? Viserys would never have stepped aside for his alleged younger nephew to claim the throne. Why risk it?

Well, based on Illyrio’s flattery, generosity and acknowledging Viserys’s claim to the throne, it is quite clear that Illyrio wanted to reduce any of Viserys’s suspicion towards Aegon being a rival to him, before the two were to meet. And indeed, Viserys never suspected Illyrio of any plotting against his claim.

“Illyrio is no fool,” Viserys said. He was a gaunt young man with nervous hands and a feverish look in his pale lilac eyes. “The magister knows that I will not forget my friends when I come into my throne.” (aGoT, Daenerys I)

At every opportunity, Illyrio addresses Viserys as king.

“Look at her. That silver-gold hair, those purple eyes … she is the blood of old Valyria, no doubt, no doubt … and highborn, daughter of the old king, sister to the new, she cannot fail to entrance our Drogo.” (aGoT, Daenerys I)

When Viserys is ired, Illyrio is quick to bow subserviently.

Anger flashed in her brother’s lilac eyes. “Do you take me for a fool?”
The magister bowed slightly. “I take you for a king. Kings lack the caution of common men. My apologies if I have given offense.” He turned away and clapped his hands for his bearers. (aGoT, Daenerys I)

He reassures Viserys’s anxiety over the claim that many houses and smallfolk would want Viserys over Robert.

“We won’t need [Drogo’s] whole khalasar,” Viserys said. His fingers toyed with the hilt of his borrowed blade, though Dany knew he had never used a sword in earnest. “Ten thousand, that would be enough, I could sweep the Seven Kingdoms with ten thousand Dothraki screamers. The realm will rise for its rightful king. Tyrell, Redwyne, Darry, Greyjoy, they have no more love for the Usurper than I do. The Dornishmen burn to avenge Elia and her children. And the smallfolk will be with us. They cry out for their king.” He looked at Illyrio anxiously. “They do, don’t they?”
“They are your people, and they love you well,” Magister Illyrio said amiably. “In holdfasts all across the realm, men lift secret toasts to your health while women sew dragon banners and hide them against the day of your return from across the water.” He gave a massive shrug. “Or so my agents tell me.” (aGoT, Daenerys I)

Like Dany, the reader (and Ned Stark) doubts this initially. From the start of Robert’s ascension to the Iron Throne though, both Jon Arryn and Robert fear that certain Lords would support Viserys III Targaryen.

“[…] I had no wish to marry after Lyanna was taken from me, but Jon [Arryn] said the realm needed an heir. Cersei Lannister would be a good match, he told me, she would bind Lord Tywin to me should Viserys Targaryen ever try to win back his father’s throne,” (aGoT, Eddard VII)

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