Why couldn't Doran send Quentyn with a bigger entourage?

[Angel Eyes]

So I'm reading a wordpress on the Politics of Ice and Fire concerning Doran's movements and wondering 'Why couldn't Doran send a bigger, better entourage to wow Daenerys'?

When Doran sent Quentyn to Meereen to woo Daenerys, he only sent Gerris Drinkwater, Archibald Yronwood, Cletus Yronwood, and a maester, the latter two are already dead by the time we meet Quentyn in ADWD. All of which are close friends of Quentyn, but given that all of them were only connected to House Yronwood, hardly the cream of the crop of Dorne. Contrast with Oberyn's entourage when he ventured to King's Landing in ASOS, which Tyrion feels intimidated by:

Quote

“Permit me to acquaint you with them, my lord of Lannister. Ser Deziel Dalt, of Lemonwood. Lord Tremond Gargalen. Lord Harmen Uller and his brother Ser Ulwyck. Ser Ryon Allyrion and his natural son Ser Daemon Sand, the Bastard of Godsgrace. Lord Dagos Manwoody, his brother Ser Myles, his sons Mors and Dickon. Ser Arron Qorgyle. And never let it be thought that I would neglect the ladies. Myria Jordayne, heir to the Tor. Lady Larra Blackmont, her daughter Jynessa, her son Perros.” (“Tyrion V”, A Storm of Swords)

Ultimately, Doran failed to wow Daenerys with what Dorne had to offer, Quentyn failed to woo Daenerys, and his chestnuts roasted on an open fire.

[Nathan Stark]

Well, because Doran never actually expected or intended Quenten to succeed. That's my guess.

[James West]

The voyage picked off the escort until they were down to Arch and Gerris.  Doran is too timid.  Too cautious.  Too many men would attract unwanted attention. 

[CamiloRP]

48 minutes ago, Nathan Stark said:

Well, because Doran never actually expected or intended Quenten to succeed. That's my guess.

A thousand times this. Why didn't Doran use his contacts in the free cities? The Sealord of Braavos, the Arcan of Tyrosh, Mellario of Norvos, or Oberyn's sellsword company? Or Sarella's mom's ship? Why didn't Quent have fine clothes to woo Dany? Why didn't he have dragon knowledge when Doran has a huge dragon book? 

[Nathan Stark]

6 minutes ago, CamiloRP said:

A thousand times this. Why didn't Doran use his contacts in the free cities? The Sealord of Braavos, the Arcan of Tyrosh, Mellario of Norvos, or Oberyn's sellsword company? Or Sarella's mom's ship? Why didn't Quent have fine clothes to woo Dany? Why didn't he have dragon knowledge when Doran has a huge dragon book? 

Yup. And I think the most important question is this; why did Doran make sure to send only Yronwoods with Quentyn, members of a house notable for its hostility towards and resentment of the Martells?

And also... Why doesn't Arianne have all these things? She's probably being set up to fail as well.

[CamiloRP]

21 minutes ago, Nathan Stark said:

Yup. And I think the most important question is this; why did Doran make sure to send only Yronwoods with Quentyn, members of a house notable for its hostility towards and resentment of the Martells?

And also... Why doesn't Arianne have all these things? She's probably being set up to fail as well.

yep, the only thing I know about Doran's plans is that they aren't what he claims

[Floki of the Ironborn]

3 minutes ago, CamiloRP said:

yep, the only thing I know about Doran's plans is that they aren't what he claims

If his plans are to kill off his two oldest kids, he's doing a good job of it. Maybe Trystane is just his favourite child?

[Alexis-something-Rose]

I don't think that Doran set up Quentyn to fail as much as he underestimated Dany. Quentyn still managed to make it to Meereen against all odds and if he had left the city after Dany fucked off on Drogon, then the odds were good that he would have managed to make it back to Dorne. 

I think Doran thought that Dany would jump at the chance to return to Westeros to take her vengeance on the Lannisters (and give him his vengeance). But she decided to stay and Meereen and rule. 

Dany is that piece on the board who refused to make the move Doran had planned for her. 

Then Quentyn decided he wanted to steal and dragon. I don't think Doran ever imagined that his son would do something as dumb as that.

[CamiloRP]

57 minutes ago, Floki of the Ironborn said:

If his plans are to kill off his two oldest kids, he's doing a good job of it. Maybe Trystane is just his favourite child?

I get you are joking, but Quentyn and Arianne weren't supposed to be in any real danger, yes, the Yronwoods want Quent to fail, but they want to marry Gwyeneth to him, so they will try to keep him safe, and they do actually. Arianne is surrounded by allies, allies who wouldn't want her to marry Aegon, but allies still.

[CamiloRP]

16 minutes ago, Alexis-something-Rose said:

I don't think that Doran set up Quentyn to fail as much as he underestimated Dany. Quentyn still managed to make it to Meereen against all odds and if he had left the city after Dany fucked off on Drogon, then the odds were good that he would have managed to make it back to Dorne. 

I think Doran thought that Dany would jump at the chance to return to Westeros to take her vengeance on the Lannisters (and give him his vengeance). But she decided to stay and Meereen and rule. 

Dany is that piece on the board who refused to make the move Doran had planned for her. 

Then Quentyn decided he wanted to steal and dragon. I don't think Doran ever imagined that his son would do something as dumb as that.

If he intended Quent to succeed he should've helped him more, he could've have him arrive earlier, and thus marry Dany, but he didn't help Quent at all, he was forced to slowly march to Mereen and he arrived late. He was also given no equipment to woo Dany.

[Arthur Peres]

Because Doran is a idiot.

Doran cautioness makes no sense at all.

He send his brother, a daring man, that already caused him trouble in the past for his out of control behaviour, obssessed with revenge, against Tywin, to meet Tywin in a city that Tywin's control... what could go wrong I wonder...

Doran saw Renly as too big a risk, against the Lannisters, but let's send Arianne to meet Young Griffin, that only has a mercenary company under him and no suport of any of the seven kingdoms... after all that went very well for the Blackfyres right?

Sending Quentyn the shy and bland boy, that never step a foot in Essos to conquest the hottest girl in the world, in a foreing land without any support, money, is just anothe average bad decision for him...

[Angel Eyes]

26 minutes ago, CamiloRP said:

If he intended Quent to succeed he should've helped him more, he could've have him arrive earlier, and thus marry Dany, but he didn't help Quent at all, he was forced to slowly march to Mereen and he arrived late. He was also given no equipment to woo Dany.

I didn’t know Quentyn was a eunuch.

[Alexis-something-Rose]

39 minutes ago, CamiloRP said:

If he intended Quent to succeed he should've helped him more, he could've have him arrive earlier, and thus marry Dany, but he didn't help Quent at all, he was forced to slowly march to Mereen and he arrived late. He was also given no equipment to woo Dany.

I'm not disagreeing with you. I just think what happened with Quentyn is part of the whole Doran is an overcautious man. He gave him gold, which Quentyn had to leave in Volantis. If anything, I think it's Oberyn who should have gone to Meereen, not Quentyn. 

I also think we're meant to contrast Quentyn, not particularly good looking, shabby and bringing the "gift" inside his boot vs the chest of court clothes and fineries for Young Griff and his companions and gifts for Dany that Illyrio sent with Haldon and Duck.

[Angel Eyes]

6 minutes ago, Alexis-something-Rose said:

I'm not disagreeing with you. I just think what happened with Quentyn is part of the whole Doran is an overcautious man. He gave him gold, which Quentyn had to leave in Volantis. If anything, I think it's Oberyn who should have gone to Meereen, not Quentyn. 

I also think we're meant to contrast Quentyn, not particularly good looking, shabby and bringing the "gift" inside his boot vs the chest of court clothes and fineries for Young Griff and his companions and gifts for Dany that Illyrio sent with Haldon and Duck.

Could Quentyn have handled the task Oberyn had in King’s Landing in ASOS?

[Nevets]

Maybe because his mission is a secret one?  No way does Doran want it known that his son is headed towards the last known location of Daenerys Targaryen - especially considering past associations and she's the Crown's enemy.  If discovered,  bad things could happen.  A large entourage would make them too visible.

He had five men with him, which should have been sufficient; they couldn't foresee a pirate attack killing three of them.  Even so, if his timing had been better, he might have succeeded. 

Oberyn is on an official state visit.  He needs to overawe the Lannisters.  Hence the large and high-ranking entourage.  Quentyn needs secrecy.  He is offering marriage, troops and political support on arrival in Westeros.  Secrecy is deemed more important than appearing impressive.

Quentyn's mission failed in large part because he was unlucky, not because it was sabotaged or because Doran was incompetent.

[Angel Eyes]

48 minutes ago, Arthur Peres said:

Because Doran is a idiot.

Doran cautioness makes no sense at all.

He send his brother, a daring man, that already caused him trouble in the past for his out of control behaviour, obssessed with revenge, against Tywin, to meet Tywin in a city that Tywin's control... what could go wrong I wonder...

Doran saw Renly as too big a risk, against the Lannisters, but let's send Arianne to meet Young Griffin, that only has a mercenary company under him and no suport of any of the seven kingdoms... after all that went very well for the Blackfyres right?

Sending Quentyn the shy and bland boy, that never step a foot in Essos to conquest the hottest girl in the world, in a foreing land without any support, money, is just anothe average bad decision for him...

Doran could have taken things a step further, started off at Norvos, disguising it as a trip for Quentyn visiting Mellario or the Free Cities in general; remember Tyrion wanting to take a tour of the Free Cities? 

[Angel Eyes]

4 minutes ago, Nevets said:

Maybe because his mission is a secret one?  No way does Doran want it known that his son is headed towards the last known location of Daenerys Targaryen - especially considering past associations and she's the Crown's enemy.  If discovered,  bad things could happen.  A large entourage would make them too visible.

He had five men with him, which should have been sufficient; they couldn't foresee a pirate attack killing three of them.  Even so, if his timing had been better, he might have succeeded. 

Oberyn is on an official state visit.  He needs to overawe the Lannisters.  Hence the large and high-ranking entourage.  Quentyn needs secrecy.  He is offering marriage, troops and political support on arrival in Westeros.  Secrecy is deemed more important than appearing impressive.

Quentyn's mission failed in large part because he was unlucky, not because it was sabotaged or because Doran was incompetent.

The secrecy in and of itself was a giveaway.

From “The Queenmaker”, AFFC:

Quote

Prince Doran was still pretending that her brother was with Lord Yronwood, but Garin’s mother had seen him at the Planky Town, posing as a merchant. One of his companions had a lazy eye, the same as Cletus Yronwood, Lord Anders’s randy son. A maester traveled with them too, a maester skilled in tongues. My brother is not as clever as he thinks. A clever man would have left from Oldtown, even if it meant a longer voyage. In Oldtown he might have gone unrecognized. Arianne had friends amongst the orphans of the Planky Town, and some had grown curious as to why a prince and a lord’s son might be traveling under false names and seeking passage across the narrow sea.

 

[Alexis-something-Rose]

27 minutes ago, Angel Eyes said:

Could Quentyn have handled the task Oberyn had in King’s Landing in ASOS?

Oberyn died in King's Landing. Oberyn's job according to Doran was to take the measure of Joffrey and his council, make note of their strengths and weaknesses, to find friends in KL, to learn what happened to Elia, and to not provoke Tywin.

Oberyn botched that because he was more invested with getting justice for Elia than anything else. I don't know how well Quentyn would have done, but I doubt he would have gotten himself killed.

Quentyn's mission to Meereen was a mess from the very start, when people recognized him and his companions at Planky Town, then went looking through his things to find a letter with his father's seal on it. 

I think the tasks that Doran gave Quentyn and Oberyn were too big for them. Oberyn was too emotionally invested and Quentyn is Quentyn, I guess.

[Angel Eyes]

33 minutes ago, Nevets said:

Maybe because his mission is a secret one?  No way does Doran want it known that his son is headed towards the last known location of Daenerys Targaryen - especially considering past associations and she's the Crown's enemy.  If discovered,  bad things could happen.  A large entourage would make them too visible.

He had five men with him, which should have been sufficient; they couldn't foresee a pirate attack killing three of them.  Even so, if his timing had been better, he might have succeeded. 

Oberyn is on an official state visit.  He needs to overawe the Lannisters.  Hence the large and high-ranking entourage.  Quentyn needs secrecy.  He is offering marriage, troops and political support on arrival in Westeros.  Secrecy is deemed more important than appearing impressive.

Quentyn's mission failed in large part because he was unlucky, not because it was sabotaged or because Doran was incompetent.

And Daenerys needed to be overawed to even consider an arrangement between herself and Quentyn.

[Nevets]

1 hour ago, Angel Eyes said:

The secrecy in and of itself was a giveaway.

From “The Queenmaker”, AFFC:

 

The secrecy wasn't the problem.  It was that they were too well known in Planky Town for secrecy to be completely maintained.  Arianne was right; they should have left from someplace bigger where they weren't known.  It is still safer than going openly, which a large entourage would necessitate.

44 minutes ago, Angel Eyes said:

And Daenerys needed to be overawed to even consider an arrangement between herself and Quentyn.

Hindsight is 20/20.  They had no reason to know that when they left.  They probably expected her to be relatively desperate.