The idea of sending a spy who is at huge risk of being turned is not a good one.

The right candidate needs to be capable of withstanding the Dark Side whilst brilliantly playing the role of Separatist convert.

They would also need some pretty high level torture Resistance if they got rumbled.

They'd probably need to be Republic zealot enough to be able to kill a few clones to get credibility.

Better if they were someone unknown to Dooku who could be embedded early and who could slowly infiltrate. Sending someone so well known means Dooku would be ultra suspicious until he could sense the Dark Side in Vos. In fact, sending a well known Jedi is really daft because alarm bells are ringing immediately. Oh yeah Quinlan, you want to be a seppy, right, we believe you.

The idea that Dooku would have fallen for the Jedi bluff of confirming Quinlan had betrayed the Republic didn't seem realistic. I wouldn't have trusted Quinlan until I could sense a full Dark side turn and watch him kill a Jedi. Otherwise he's under permanent suspicion and not to be trusted with classified info.

If you could find someone initially inconspicuous but extremely useful who probably isn't a full blown Jedi but is really good at blocking force attempts at mind reading/influence, you'd be on to a winner. Someone who could insinuate their way into Dooku's trust.

TLDR: No, Qunilan is too vulnerable to the Dark Side and too well known. It made a fun story in Legends and Canon but, if you want classified Intel, it's the wrong way to go about it.

^You make some valid points Ctmeh. It might’ve been better to choose/find someone more unknown to Dooku to lessen the chances of him discovering the true intentions of said candidate. However I do think that finding a suitable candidate who’s both capable of pulling off faking dark side seduction while avoiding actually falling to the dark side is very difficult. Luke, Quinlan, Ulic, and Cade are all characters who’ve tried faking it and in the process they either came close to actually falling or they actually fell. With the Clone Wars raging throughout the galaxy, the Jedi were very preoccupied with their new roles as generals so I also think that having the time to prep a suitable candidate for this role would’ve been taxing. 

There’s also the fact that Dooku is normally untrusting of newcomers. As we’ve seen in both continuities Dooku’s potential followers had to prove themselves to be legitimately susceptible to the dark side and both Dooku and Sora sensed that Quinlan. This is one of the main reasons Dooku orchestrated the attack on Kiffex. Once Dooku pushed Quinlan to use his psychometry abilities on Tinte…well yeah see below lol. 

Pulling one over on Dooku is something that only a select few have been able to accomplish (looking at you Palpy). To undertake a mission this dangerous, a seasoned warrior is much more suitable and Dooku, being a veteran himself, knew a great deal of the Jedi in the order. This would mean that they would probably have to train a brand new Jedi which would be a daunting task given the war at hand.

Yep you are right, of all of the Jedi, Vos is probably the most likely to play the part of a dark sider. But that is mainly because he is so susceptible to it.

Perhaps Jorus C'baoth might have been a decent choice because he's such a prick anyway you'd well believe he'd do the dirty on the Jedi. Obviously, being dead at that point kind of rules him out.

Like you say, if anyone could withstand the Dark Side, you'd go Luke but even he fell.

Which is why I wouldn't have sent a Jedi. Too risky. Probably better to use someone non-force sensitive but mentally very strong.

Or stick some kind of hack in a tactical droid like Kalani.

Vos, bless him, is a hot mess. In Canon he ends up having Ventress trying to save him from his own personal chaos. That says all you need to know about his stability.

Love this post by the way.

^Thanks Ctmeh 😊. This storyline has always greatly intrigued me and I love that the Jedi council regularly debated the ethics behind sending Quinlan into Dooku’s neck of the woods. You present some good alternatives here. Had Jorus C’Baoth lived a little longer, he could be a likely candidate for this mission. Dooku would probably like C’Baoth and he might’ve even been besties with his clone. He was ten times the prick that his original version ever was lol. I like your hacking a droid idea as well. I hadn’t considered that idea and it would be pretty effective since the separatists are known for their droid armies. Just have to be careful not to let a Jedi turn it into scrap metal. Like you and I have pointed out, Quinlan is very susceptible to the dark side and many others had to help him remember that giving into the dark side does more harm than good.

Given your alternatives and given the numerous other Jedi undercover opts we know about involving the dark side, I’m leaning towards being against this if I was a member of the council. I mean, thank god, Quinlan’s time in Dooku’s cult didn’t fully turn him in the end but it came very close to doing so on more than one occasion. You could possibly end up creating another Dark Jedi, potentially another Sith, by sending someone with his background into Dooku’s organization. That being said, Quinlan handled his dark side encounters better than a certain other Jedi in this era would’ve (cough* Anakin cough* 😏).

Oh my god yes, Dooku and Joruus would have been insufferable, sneering best buddies.

I know you have some reservations regarding Canon but have you read Dark Disciple? It is a good read. An interesting take on Vos and Ventress.

^Been a long time since I read that one but I didn’t care for Ventress falling in love with and dying for someone she didn’t really know. Felt a little too much like Khaleen’s story but not as well developed imo. It wasn’t bad but it wasn’t great for me either. It was nice to see Quinlan not be the hippie he was in his TCW appearance though. That was just…no lol.

I always saw it as Ventress being so mistreated that she really wanted her relationship with Vos to be important and meaningful. To give her life a sense of meaning after all the brutality and malice.

Yes, in TCW he seemed like he was only a small step away from sparking up a jazz cigarette and trying to find common ground with a B1.

^Fair point. Ventress was long overdue for some positivity in her life. Also yeah TCW Vos was really bought that life lol. Every time I see him, I’m like “Can somebody get him off the stuff?”.

'Like bruuu, battle droids and Jedi are like the same and different but that's okay dude. We should put down our weapons and pick up our hearts dude.'

I would be even more sympathetic to Ventress but there was the Clone impale/kiss business...

^Ahhh yes, death by kiss…Obi Wan stick with Satine because this one is more than you can handle.

I’m pretty sure Quinlan came back from making his death stick delivery when he met up with Obi Wan. Why the Jedi sanction such behavior, I’ll never know 🤔.