Flynn Fairwind

Flynn Fairwind is a human from Kul Tiras. A former pirate captain, he now serves the interests of Kul Tiras as long as he gets paid. He is the captain of the Middenwake and the Bold Arva. Flynn styles himself as a charismatic and dashing rogue, with seedy contacts throughout Tiragarde Sound and a talent for improvising to turn a bad situation around. However, he has a habit of being captured or humiliated and needing to be bailed out by his friends, typically the adventurer or Taelia Fordragon. Still, Flynn remains a loyal and honest friend, as well as an asset to the Alliance.

Flynn serves as the Alliance manager for island expeditions, and a major character in the Tiragarde Sound storyline, where he helps the Alliance ambassador uncover the connection between House Ashvane and the recent pirate attacks in Kul Tiras. Flynn also personally aided Mathias Shaw during the events of Shadows Rising.

Though his mother always insisted that she was a barmaid, a young Flynn discovered that she was really a thief. He was initially angry and sad that she didn't trust him with the truth but came to the conclusion that any mother willing to risk life and liberty for her son must be full of love. However, his mother was eventually caught and Flynn made himself go and watch her execution by hanging. Sometime afterward, he was taken advantage of by the local gangs, who had him picking pockets and distracting guards for them.

Flynn eventually came to be the captain of his own pirate crew, with Harlan Sweete as his first mate. He witnessed Harlan commit acts that he didn't like, leading Flynn to consider him a maniac. The apparent last straw was when the two had a falling out after a messy job and this, plus his disgust over Harlan's behavior, caused Flynn to lose all taste for freebooting, so he just disappeared from Freehold one day. Venrik even came to believe that he had died. Meanwhile, Harlan took the nastiest of the crew and formed the Irontide Raiders.

Flynn met or came to know of Taelia Fordragon while he was still a pirate and developed a crush on her. Even though he would go on about her all the time, he appears to have not have mentioned her by name to his compatriots like Venrik, describing her as having "hair like raven's down."

Flynn was encountered by an Alliance adventurer as a prisoner in Tol Dagor, the island prison owned by House Ashvane. He had intentionally gotten arrested because Cyrus Crestfall hired him to break the adventurer out of Tol Dagor. Flynn staged a prison break and met with Taelia, who was waiting with an escape boat to take them back to Boralus.

Flynn later worked with Mathias Shaw to retrieve the Abyssal Scepter, a stolen tidesage artifact, from the Zandalari treasury. The serious spymaster didn't get along with Flynn at first, not appreciating his quips, but seemed to warm up to him by the end of the scenario. Once the real scepter was taken and swapped out with a fake one, they made an escape from Opulence.

He can also appear drunk in Boralus during the Faction Assaults.

After winning the Bold Arva in dice, Flynn and his assembled crew were tasked with aiding Mathias Shaw in his mission to further intelligence on the possibility that Banshee loyalists were within Zandalar. In light of the storm brewing, Flynn directed Shaw below deck, declaring that Shaw didn't have the sea legs for it and that he was too drunk. While below deck, Shaw received messages from Swailes from his agents Narsilla Keensight and Krazzet. When Flynn learned who the messages were from, he declared it very paranoid of Shaw. While acknowledging that they signed an armistice with the Horde, Shaw pointed out that it doesn't mean that they weren't watching them. He then stated his belief that only a fool mistakes peacetime for complacency.

Flynn then asked what was happening within the Horde, and Shaw revealed that an assassination attempt was made on Queen Talanji of the Zandalari Empire at a Horde Council meeting. While Shaw was pleased to have had eyes on the assassination, Flynn wondered if the storm around Zandalar was caused by Talanji as a way to keep the whole island on lockdown, with nobody going in or out until they found the assassins. Unbeknownst to them, the storm had been created by Apari, the leader of the Widow's Bite who was behind the assassination attempt on Talanji, as a means to isolate her.

As the mission progressed, Shaw found himself bonding with Flynn and greatly sympathized with the other man when he learned that Flynn witnessed his mother's death by hanging for thievery. After landing on Zandalar to avoid the storm, Flynn suggested making their way to Fort Victory. However, Shaw revealed that after the armistice with the Horde was signed, they ceded control of those encampments and that any sign of them on Zandalar shall be taken as an act of aggression. In light of this knowledge, Flynn's first order of business was to hide their ship. Though Shaw privately thought it was wiser to stay abroad the ship, he consented to the group going on land, understanding that morale was low and a brief stint on land always did a sailor good.

After disembarking the ship, Shaw spied a Widow's Bite camp and upon investigating it, he discovered evidence suggesting that the group was in working with the Banshee loyalists. He then ordered Flynn to get the ship ready to sail, while he gathered more evidence only to end up captured by the Zandalari. While a distressed Flynn and the crew made it with all haste to Kul Tiras in the hopes of getting rescue for Shaw, the spymaster was thrown into a cell within Dazar'alor.

After arriving at Boralus, Flynn subsequently barged into House Proudmoore's dining hall to reveal that the Zandalari had taken Shaw prisoner. While Turalyon and Alleria Windrunner sought to respond with war against the Zandalari, convinced that they were working with Sylvanas Windrunner, Jaina Proudmoore called upon them to not add fuel on an already kindly fire and risk the treaty. Jaina then stated she would use the treaty itself before turning to the blade.

Flynn was in Stormwind when Shaw was released from Horde custody and returned home. He was so overjoyed to see Shaw freed nearly shoved King Anduin Wrynn out of way to wrap him in a tight warm hug, that Mathias returned. Shaw then revealed that there was something that he wanted to talk about with Flynn and asked him to meet at the Gilded Rose that night, causing the other man to blush which said all that Shaw needed to know.

After they returned from Zandalar, Flynn and Mathias barely interacted with each other until one day when Flynn won a treasure map of Duskwood in a card game and convinced Shaw to come with him for an adventure and a bit of fun. Near the Tranquil Gardens Cemetery, the two came across the Night Watch commander Sarah Ladimore suffering from a mysterious rotting illness and brought her back to Darkshire, where she revealed that she had been attacked while investigating a report that the Torch of Holy Flame—an artifact used to keep the undead of Duskwood at bay—had gone missing from where it had been placed on Forlorn Rowe. During the conversation, more injured Night Watchers arrived and revealed that an army of undead was heading from Raven Hill to Darkshire.

Flynn and Mathias set out for Raven Hill on gryphonback. Along the way they passed over the Twilight Grove and agreed that they would head to a moonwell for their next, more peaceful adventure. Upon reaching Forlorn Rowe, the two rogues quickly discovered the culprit responsible for stealing the torch, a human necromancer, and (after Mathias offered some encouraging words to his companion) followed her down into the Dawning Wood Catacombs while avoiding detection by her undead minions. In the deepest level of the crypt, they found the necromancer attempting to corrupt the torch within a ritual circle. Mathias revealed himself and began talking with the necromancer to distract her while Flynn used rum from one of his bottles to wash away the bone powder making up the circle. While Mathias attacked the necromancer, Flynn grabbed the torch and realized that it could be cleansed of corruption in a moonwell. The necromancer managed to curse Mathias with the same rotting disease that had afflicted Ladimore, but the two rogues used their blades and the torch to fight their way out of the catacomb and used one of the Night Watch's left-behind gryphons to escape to the Twilight Grove. The necromancer pursued them on her winged undead horse and blasted them off their gryphon as it came down to land in the grove. Although his skin was now covered in sores, Mathias declared he'd keep the necromancer busy. As Shaw and his opponent fought, Flynn plunged the torch into the moonwell, reigniting it and allowing him to use it to set the necromancer aflame and kill her.

With the necromancer's death, the illness affecting Shaw and Ladimore vanished. The Torch of Holy Flame was returned to Forlorn Rowe, and Ladimore commended the two rogues for saving Duskwood. As they didn't get to complete their treasure hunt, Mathias gave Flynn's map to the Night Watch, and the watchers returned with the treasure as a gift to the rogues: a hand mirror. Afterward, Mathias told Flynn that there were many powerful artifacts like the torch scattered across the world and that King Anduin frequently sent him to check up on them. With Azeroth relatively quiet for the time being, it was time for Shaw to go on an inspection trip—and he wanted Flynn to come with him on the journey. When Flynn asked why, Mathias simply responded "Because I trust you". Flynn agreed, and the two kissed.

When Shaw was granted a temporary leave by King Anduin Wrynn to travel through the Eastern Kingdoms in order to write up reports on its people, on its places, to inventory some powerful artifacts and ensure that they are safe, but also to meet contacts of the Spymaster to collect as much information as possible on the situation of the continent, Flynn joined him, claiming to want to "prove my worth by assisting the Spymaster and his right Royal Majesty King Anduin."

For the sake of their mission and relations between the two factions, the duo obtained permission from the Horde Council, signed by Baine Bloodhoof, to pass through Horde territories without being attacked.

Following their mission, Shaw and Flynn managed to find the lost crown of the late King Terenas Menethil II, buried in a secret memorial behind the Stormwind lighthouse. The duo believes it was done by Lordaeron refugees who buried it there, so the survivors of Lordaeron would have a place to mourn their king, and that neither Arthas nor anyone can ever find the crown. After verifying and confirming the presence of the crown, they buried it once more and agreed to continue keeping the secret, without telling Anduin anything about it.

Flynn accompanied by Shaw was among those who attended the wedding of Lor'themar Theron and Thalyssra. During the reception, he spoke with Taelia, where he discovered that Jaina Proudmoore didn't attend the wedding due to the kingdom experiencing pirate troubles. He subsequently inquired as to their flags, in order to see if they were old mates of his and thus could provide aid in handling them.

Flynn bought a pet from Wilder Seabraid of T&W Trading Post as a surprise for Shaw. Later, he can be found at SI:7 headquarters.

• Zandalari Treasury
• Roll the Bones

• Azerite for the Alliance
• Freehold: A Pirate's End
• Island Expedition (Alliance)
• Island Expedition (2) (Alliance)
• Worldvein Rumors (Alliance)
• Sampling the Goods
• Stow and Go
• Under Their Noses
• Dress to Impress
• Freehold (quest)
• Lovesick and Lost
• Papers, Please
• Rodrigo's Roost
• The Big Job
• The Irontide Crew
• Lured and Allured
• A Local Guide
• An Explosive Entrance
• Sweete's Strongbox
• The Keys to Success in Freehold
• The Mysterious Island
• Tol Dagor: The Fourth Key
• Daughter of the Sea (quest)
• Message from the Management
• Out Like Flynn
• Small Haulers
• Suspicious Shipments
• The Smoking Gun

• Out Like Flynn
• Cultural Significance (Alliance)
• Not Too Sober Citizens Brigade
• Stow and Go
• Lured and Allured
• Lovesick and Lost
• Fairwind's "Friends"
• Tol Dagor: The Fourth Key

• Greetings
• Ahoy!
• I'm all ears.
• A job's a job mate!
• Blood or gold, everything has a cost.
• What's the word?
• Are you thirsty? I'm thirsty.
• What's your story?

• Farewell
• Watch your back out there.
• Keep your powder dry!
• Eyes on the horizon.
• Next rounds on me.
• See you around.
• Let's get paid!
• Don't look back.

Cagney fished this girl out of the water with his ferry - said she was trying to escape the foundry.

• At Eastpoint Station

Doesn't surprise me one bit that the Ashvane Company is putting kids to work. I was barely older than her when the gangs in Boralus had me picking pockets and distracting guards for them.

In this world, the weaker you are, the more people take advantage of you.

Fortunately the workers don't seem to mind us snooping around... just the company goons.

• At Ashvane Foundry

You get what we need?

Let's split up.

• Outside Freehold

You investigate the docks, I'll see about getting us into town.

Good news: I think they're gonna let us in.

• Near the entrance to Freehold

Bad news: We technically have to become pirates to get in.

What, were you worried? Haha!

• Vigil Hill

Ah... still a bit sore. But I'll be fine.

Besides, my job's done, mate.

You and Taelia go on back to Boralus and do the hero thing.

Oh, I don't know, maybe find me someone nice, settle down on a little farm somewhere...

What do you THINK I'm gonna do, mate?!

I'm gonna get my money from Cyrus, buy everyone a round at The Snug Harbor, and look for the next adventure.

Only way to live, my friend.

Yes? We've got our orders, the Azerite's waiting, just take a look at the table and you let me know when you're ready to ship out.

• In Boralus

I'm know, I'm hard not to look at, I get that a lot, but we've got to focus here.

Nice to see you ! Hope you are enjoying yourself in SI:7, I keep telling Mathias he needs to spruce the place up.

• At T&W Trading Post and SI : 7

• World quests
• Swab This! (Alliance)
• The Winged Typhoon
• Captain Wintersail (quest)
• Ghost of the Deep (quest)
• Watch Your Wallets
• Squirgle of the Depths (quest)
• Squacks (quest)
• Adhara White (quest)
• Carla Smirk (quest)
• Polly Want A Cracker? (Alliance)
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• Enemies arriving
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• Winning
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• Successful end
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• Flynn likes people who are kind to animals.
• Flynn has a history with Captain Keelson of The Maiden's Virtue, a smuggling ship. Whatever happened between them, he does not want to be seen by her.
• Flynn is bisexual. This is shown by him currently having a relationship with Mathias Shaw despite his previous crush on Taelia.
• His generic names are Tol Dagor Inmate (during Out Like Flynn), Boralus Privateer (during Dress to Impress), and Kul Tiran Sailor (during The Keys to Success in Freehold).
• His mounts are a horse and a parrot.
• Flynn is voiced by Henry Lloyd-Hughes.
• Flynn's name and general personality may be inspired by Flynn Rider from the 2010 Disney movie .
• In the short story Terror by Torchlight, Flynn repeatedly swears "By the Tides!" or "Tides!", much like most Kul Tirans do due to a belief in the Tidemother.

• Generic names