The Gentleman has been purposefully vague with his history to The Mighty Nein, who only recently came under his employ. However, he got a bit braggadocious with Nott when she questioned why they should trust him, and gave away a little sliver of information: he’s been operating in Zadash for 15 years. That’s given him enough time to build a bar, a bar under that bar, and his underground smuggling operation under that, called the Underworks (rather appropriately named, all things considered). Prior to that, we can’t be entirely sure, other than piecing together bits and pieces.

When The Mighty Nein first entered his domain, The Gentleman questioned them on their belief in luck, and that he found it important that his investment is lucky. He then played the Gambit of Ord with Fjord as a show of confidence. In their last meeting, The Gentleman mentioned to Fjord that he has a main contact in Port Damali (“The Jewel of the Coast”) named Father Dwandath Pierce, who heads up the temple to Avandra, the Changebringer. While we don’t know if The Gentleman is a devout follower of the Changebringer, he certainly favors her divine leanings in his business.

Two other pieces of information can be gleaned from these encounters. First is that the Gambit of Ord is very specifically a game from Marquet, which is very far from Wildemount. Marquet is in the far southern reaches of the Ozmit Sea, the ocean separating the western side of Tal’Dorei from the eastern side of Issylra. The ocean separating the eastern side of Tal’Dorei from Wildemount is the Lucidian Ocean, which is notoriously treacherous to cross. The Gentleman being familiar with the Gambit of Ord is a clue that he’s met people from there, or has been taught by someone who had been to Marquet, or is even from somewhere closer to there. The Dwendalian Empire is notoriously insular, especially since it’s functionally landlocked, so it’s more likely that The Gentleman didn’t start his career in the Empire. Also, considering that he hasn’t been back to Port Damali in years—since he can’t leave his business unattended—he probably started elsewhere and then settled, rather than residing in Zadash, moving elsewhere, and then coming back.

Second, The Gentleman made sure to let Fjord know that most criminal business in Port Damali was not in his network. We know from Howaardt Darrington in Campaign 1 that “Wildemount is the Myriad in many ways.” The Myriad is a large criminal network throughout the continent, and we had initially thought that The Gentleman was a part of it, thanks to his “many gifts” line (in order to get into the Myriad bar, Vox Machina had to mention they wished to speak to The Many). However, given that the Myriad is so prevalent in that part of the continent, and The Gentleman said that his network is specifically not, we’re more inclined to think that he operates outside of their grasp.

Smuggling

The Gentleman describes his business as, “A company that specializes in the completion of the tasks and trading of things. Perhaps not the most legal. Things that are restricted by the Empire. That means our skills are best through speed, subterfuge, darkness.” The Dwendalian Empire, with its constant martial presence and strict religious restrictions, provided a fertile ground for smugglers to grow their businesses. The Mighty Nein witnessed several of examples of what The Gentleman deals in. The reason they knew about him at all is because Beau stole mail that was to go to the Baumbauchs because they weren’t nice to her in Trostenwald. One of those letters was to Demedan Baumbauch in regards to a shipment of bloodroot, a non-lethal poison, which is apparently illicit enough that he had to mix up the letters in bloodroot when he sent it.

When TM9 were brought to the Underworks for the first time, Caleb heard and glimpsed, through Frumpkin, a series of cages with creatures in them. Though they couldn’t ascertain the nature of these creatures, the sounds they were making as the underlings whipped them didn’t sound humanoid, so slave trafficking is likely not their business. It’s also telling that The Gentleman aligned himself with Ophelia Mardun and not the slave trafficker Jagentoths in Shadycreek Run. Kara told Beau, “Most of the folks that work for The Gentleman and that we work for are well-paying because they’re well-off. Some of them aren’t the most moral, either. We don’t do anything that hurts the folk that don’t deserve it. At least, as far as I know. We don’t kill, we don’t murder. We just move and sell and deal in various goods that aren’t perfectly legal.”