Sir Windward

If you've ever been to the Tri-City, you definitely have heard of the Windward Contract Agency, at least in passing. Some denounce them as heartless mercenaries, some respect them as independent contractors with many different options. But what they really do is often obscured or blamed on someone else.
Sir Windward is the Agency's leader, company man, head manager, whatever you might call him. He inherited it from his father, and made it a name not just in Adzameh¹, but in the entire Triad. The Agency's elite (and most expensive), the Committee, answer directly to him (and, in fact, they live with him in his flying tower-mansion. Murder roommates!).

As I say above, he's trans, but most don't know this. See, young Robbie here was his parents' only daughter, but he cared about their legacy, which opposite to most Athamian lineages had a man be the one to inherit the line. He pretended to be his own brother, which turned out to be strangely fitting, so he faked his own death and started presenting as a man full time.
Those who he doesn't trust sufficiently and learn of his transness, he usually blackmails, but not if they're clueless enough to not know the exact details - not because the society he lives in is transphobic, no! In fact, quite the opposite - transitioning is a deeply spiritual process for many who live in Athame (specifically, the native Wattite religion), involving various rites and sacraments depending on the nature of the transition ("to transform one's essence into a truer one is a great change which must be properly assisted, lest the darkness take you") - but among those rites, for trans men ("roots", as they grow from the sky into the earth), is fasting and purification.
Windward's quite the hedonist, and not very pious. So he decided to go hard in the other direction, and transition by transmuting his flesh into the same thing, just with different chromosomes and hormone production. Biotransmutation is a highly taboo topic, considered forbidden magic, so I often joke that his transition broke the Geneva Convention.

Fun facts:

• A bit of a casanova. Men and women want him, but he only really ever has short flings, a lot of which are for the purpose of gaining leverage. Get it, grandpa.
• Chopped off his right arm and replaced it with an expensive technomagical aug², which he primarily uses as a very powerful and efficient casting focus for his preferred lightning magic. Also, it looks cool.
• Chainsmoker (usually found with a cigar in his mouth). Thank the Sun for modern magic and science, else his lungs would be completely rotten 3 decades ago.
• Owns a heirloom blunderbuss and sabre, but usually only uses the former, and the latter is just for show.
  
• The transmutation changed his internals, but not the externals. Old man saggy titties
• The oldest OC of the TTP universe (about 4 years old now?). In fact, he was the first, and the universe kind of slowly grew around him.

₁Alternate spelling of Athame, more closer to how it is pronounced and written in native Athamian, rather than the softened spelling used in typical Triadic (which is equivalent to DND Common - it's a simplified constructed language used in city-borne interplanar communications, and for the sake of the translation convention, equivalent to English). The "h" is silent and only there to not make the word end in a vowel, which is problematic because of the way Athamian is written.

₂In-universe slang for advanced prosthetics, implants, etc. Short for augment.