What We Know About: The Gentleman

Thanks to @souratgar for this art piece!

Since Beau committed mail fraud back in Trostenwald, The Gentleman has been an enigmatic figure in the lives of The Mighty Nein. In light of some discoveries in Nicodranas of just how far his history and reach stretch even beyond the Dwendalian Empire, we thought it necessary to highlight what we know about everyone’s favorite water genasi crime boss thus far. Updated to 2-33.


We haven’t seen many genasi in Exandria as of yet, but that’s to be expected. Genasi are the result of a few rare occurrences: being the offspring of a genie and a mortal, the offspring of two genasi, a mortal who has a genie somewhere in their lineage, or someone whose parents were exposed to a huge surge of elemental power. In D&D, there are four types of genies, each linked with an element: efreet (fire), marid (water), dao (earth), and djinn (air). Genasi don’t have to be from any particular area, though it would make sense that there would be more water genasi where there are potentially more marids, for example.

If you watched Campaign 1, you saw a number of efreet: Vox Machina fought one in Pyrah, and encountered many of them in the City of Brass in the Elemental Plane of Fire. VM also battled one marid when their ship was attacked on the way to Vesrah. In their travels, Vox Machina only encountered one genasi: Senokir, the fire genasi in the City of Brass. So far, The Mighty Nein have encountered two: Headmaster Oremid Hass, an earth genasi, and The Gentleman, a water genasi.

In D&D fifth edition, player character options for genasi are outlined in the Elemental Evil Companion. These individuals are somewhat otherworldly, though still humanoid (unlike their genie relatives, which are elementals). They age at about the same rate as humans, but live a bit longer. Their appearance is influenced by their particular elemental heritage, as are their associated abilities. The Gentleman, for example, has blue skin, and looks like he’s perspiring all time. The constant perspiration (and Nott’s derision thereof) is a small price to pay considering he’s able to consume acid and only take half damage. He can also breathe underwater, has a swim speed of 30, and can cast Shape Water (cantrip) and Create or Destroy Water (2nd, once per long rest).


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.


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.”

The Gentleman, as part of his original dealings with The Mighty Nein, agreed to smuggle Horris Thrym out of Zadash and up to Berleben while everything with the death of the High-Richter blew over. The Nein were incredibly dubious that Horris would make it there alive and well, but were delighted to discover that he was surviving well when they reached the city several weeks later.

The Mighty Nein got to see the nature of the goods The Gentleman and his crew smuggle when they freed his safe house in the Labenda Swamp from the merrow. In addition to a number of sets of silverware and weaponry, they uncovered a veritable pantheon of religious iconography for gods banned by the Empire. Some of those gods were good, some were neutral, and some were evil. It can be argued that on a certain level, The Gentleman was helping people survive in an empire that sees fit to stifle their religious beliefs because The People In Charge Say So (even if the primary reason is profit).

That all being said, The Gentleman has cultivated a reputation for being terrifying and willing to have people killed. Claudia Sheed, the owner of the Leaky Tap when The Mighty Nein arrived in Zadash, warned Beau and Jester, “I do not know him, but I know of him. That thing I said about trying not to get in trouble with the darker elements of the city that might be in over your head? That is very specifically one who wallows in that mire.” Similarly, when Beau and Nott got Thed, the Zadash sewer smuggler, to tell them how to get into the Evening Nip, he told them, “If I give you any more information and that gets around, I am deader than that spider would have left me.” Upon bringing Caduceus into the Evening Nip, The Gentleman cheerfully told them that the options were to take a vial of Caduceus’ blood, or kill him immediately.


From what Marion described to Jester, the man who is her absentee father had blue skin, sweated a lot, had a tuft of dark chest hair, wore a lot of rings, lived at sea, was charming and funny, and was named Babenon Dosal. From what Jester described, he had expressed a mutual interest in getting married to Marion, but said he had to go settle his affairs and his house, and then never returned.

When Jester sent messages to The Gentleman asking if that was his name, he didn’t respond. When she asked if he knew the Ruby, he said it was preposterous. It should be noted that he never mentioned that he’s been to Nicodranas, even when Fjord mentioned they were heading there.

As a reminder, we attempt not to speculate beyond the facts as we know them. We’ve put together two quote compendiums for you to dig through at your leisure: one for The Gentleman and one for Jester’s Father.