Jakarn is a womanizer, and with his smooth talking he has captured many hearts on the island. Among them are Irien, Nasmat, and Elethien. They all meet on the ship later and the three women want him to make up his mind or they'll throw him overboard.
Jakarn wound up with the other dissenting crew members with Captain Albert Marck and joined his crew in Wayrest. If the Vestige interacts with him, they will know what he has been doing since leaving Captain Kaleen's crew.
During the quest "Innocent Scoundrel," Jakarn can be interacted with after finding him in his cell. Afterwards the Vestige helps Jakarn to retrieve a stolen gem that he hid within a nearby goblin camp.
Now that the Vestige has recruited at least one of the people Kaleen wanted, we can pull off her heist whenever ready. The goal is to break into Headman Bhosek's palace and steal the shipping logs from his lockbox.
This quest is one of three quests within The Bloodthorn Plot quest line one must complete to proceed. Laganakh senses evil spreading on Betnikh and the need to know what's facing them before fighting, a use of a totem can bring up visions that might be of help.
Jakarn is one of Captain Kaleen's crewmembers who opposes the retrieval of the ancient necromantic weapon for use of the Daggerfall Covenant, claiming it to be too dangerous a weapon at the same time complaining how life would be without challenge with the weapon in their hands.
Jakarn can first be encountered imprisoned in the Grave.
"Hey, you're not a guard. Get me out of here. Please!"
- Did you steal from Headman Bhosek? "Is that really important right now? Bhosek stole it from someone else. Can't steal from a thief. If you get me out of this, I'll owe you big."
After releasing Jakarn from his cell and nearing the main exit of the Grave, he will wish to speak with the Vestige.
"We can't go that way."
Why not? "Irien's out there. Oh, and guards. I saw many, many guards. Look. Let's slip out a side exit. That way, we can both keep our heads."
After exiting the Grave through the side exit, another conversation will follow.
"Thanks for breaking me out back there. Listen, while you're in a heroic mood, want to help me get something I left with the Goblins?"
You gave something to the Goblins? "I figure, if you want something kept safe, give it to the Goblins. They'll watch it for free, they're too stupid to trade it, and they'll kill anyone who tries to take it."
- Won't they kill you if you try to take it? "Here's the thing. You went through a lot of trouble to free me, right? There's no way you'll let me get eaten by Goblins. So you, my good friend, will follow me to their mine. Yeah?"
After entering the Dogeater Goblin Camp, Jakarn can be found near the entrance of the mines.
"I unlocked the door. Now we can retrieve my gem. I'll see you inside."
What does the gem look like? "It's as pretty as a thing can be. And as big as my two fists."
Jakarn can be them found near the entrance of the main chamber.
"This is the part where I trust you."
What are you talking about? "I'll kill the Goblins in the scaffolding in the next room. You grab the gem. It's in a chest on the floor. There's a passage on the far side. Take that and meet me outside. If something goes wrong, regroup at the inn in town."
Once the stolen gem has been recovered, Moglurkgul can be found outside, looking for Jakarn. At this point the Vestige is able to choose whether to give the stolen gem back or keep it.
Jakarn can be later found in Screaming Mermaid, surrounded by a fresh pack of admirers.
If the Vestige had chosen to return the gem:
"Glad to see you made it out."
I met Moglurkgul outside the cave. She's got the gem now. "Well that's a shame. Still, getting Moglurkgul off my trail is a good trade. She's relentless. I'll be honest. I'm just a little hurt. But since you saved my life, we'll call it even."
- You owe me a favor. "Yes. Yes, I do. I know someone on the island who can make us both rich. If you're up for another job, I think it's time you met her."