Theo Windingbrooke



Theo is a fairly tall halfling at 3’9". His unusual white hair gives the impression of a more advanced age, but in truth he’s just 36 years old. He comes off as a bit devil-may-care and is prone to projecting something of a superiority complex, ruining some of his good looks.


Born and raised in the Andeferan capital of Cydweli, Theo was always seen as a gifted child and was ushered into the world of academics and mages. Though he routinely shirked his apprenticeships and scholarly duties, he did indeed display aptitude in spell-craft and intellectual pursuits.

The problem was that he found it all terribly dull. Spells are great, esoteric knowledge is great, but as soon as he’s asked to chart a spell’s astral imprints, organize the library, restore degraded parchments of old royal lines, take stock of the alchemical supplies or just about anything else that lacked any kind of sex appeal… Well, he just couldn’t be fucked to do it. He’d run around town instead, rubbing elbows with other people who are supposed to be somewhere they’re not and delving into shenanigans.

Figuring he’d learned enough to make a go at the world, he looked to break free of his obligations in Cydweli. With letters of resignation tactically placed (as well as another that ends “Please understand Kadie, no sort of fault belongs to you, rather the fault is mine alone.”), he slipped out of town to make his mark upon the world, away from his smug and overbearing family, away from Headmaster Myldwin, and away from a string of mentors that never could make a proper apprentice out of him.

Theo’s Current Situation

He arrived in Oakengate and found himself hugely undervalued by the local populace. No matter, he could make his way. He picked up odd jobs, met some people he really didn’t like, stole some stuff from said people, met some new business contacts, found new sorts of odd jobs. Yes, Theo became a bit of a thief, but not a callous one. In order for him to try and swindle someone, he’ll have to believe that the target truly deserves it or that the holdings in question would hardly be missed at all. Furthermore, thieving is more of a supplementary activity done out of necessity. Certainly, when honest work is made available to him, he’ll always do that first… provided it’s not too dull… and so long as the boss is alright.

Among his contacts is one Bardo Banksi. When Theo needs to sell something that is simply too hot in Oakengate, it goes to Bardo who can sell at another port. When Bardo has product that was too hot elsewhere, Theo facilitates such sales in Oakengate.

A Mysterious Correspondence

Recently, Theo had received a letter from Caedda Aethelnod, the antiquities director at the Cydweli Institute of Mysteries (Theo always thought that name oversold what he saw as an oppressively boring place). The letter read as follows:

“In address to Sir Theo Windingbrooke,

I hope you’re in good spirits and enjoying the new life you’ve chosen for yourself in Oakengate.

I recall you spent some time with Professor Flerrehdy. I’m sorry to report his death, though I hope you take comfort in his passing peacefully in his home. Of course, Flerrehdy was a remarkable expert on Miki culture and history and spoke highly of your potential. My department has come into possession of a Miki inscription. We believe it comes from a prominent Miki druid named Eno Sakoya from the time of the rift’s rising. Its presentation, though it has suffered from time’s ravages, denotes it was of some importance. There are disagreements as to it’s potential meanings. Leddy believes it speaks to the unification of the Miki islands. Others of course look to writings from this time to find answers regarding the rift’s arrival. I’ve been asked to get your opinion on the inscription. It reads as follows: ’ [eroded] … (p)eople in this world, served poorly by kings wanting calm. In truth these events [eroded] … on the s(ur)face of a pool. Our sphere has bordered others, never quite [eroded] … or they [eroded] … stronger now, though there is violence in the joining. As for [eroded] … will find evidence [eroded]… a dragon, wings folded, looking north over the sea. Further inland there [eroded] … We’d be wise t- [eroded]’

We look forward to learning if your studies with Professor Flerrehdy provide you with any insights to this admittedly incomplete and cryptic text.

Best wishes!

-Caedda Aethelnod"

Theo had responded with puzzlement of his own. The only response he got back was news of Caedda’s unfortunate death, which occurred peacefully in her sleep.

Additional Information

Theo knows the following spells:

Mage Hand (cantrip)
Fire Bolt (cantrip)
Minor Illusion (cantrip)
Disguise Self
Silent Image

Due to his “Sage” background and high intelligence, Theo is a wellspring of knowledge on just about any lore subject, and when he doesn’t know a piece of scholarly information, he usually knows where or from whom such information can be learned.

Theo Windingbrooke

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