Dour Orlando

## Orlando

**Orlando**, better known around Port Nyanzaru as **Dour Orlando**, is a Amnian fence once affiliated with the Shadow Thieves of Amn as well as the proprietor of the *Gray Trader*, a general store used as a front for his criminal business. When Port Nyanzaru gained its independence from Amn in 1482 DR, Orlando became an unaffiliated criminal, working with the few thieves and criminals he believed he could trust in the former colony. In 1490 DR, he was coerced into working alongside the smugglers Florina DuRaal and Red-Eye after the Zhentarim Viper threatened the life of his daughter Sana. After the plot of the smuggler captains was stopped by an adventuring party, Orlando was pressed into service to the Merchant Prince Jobal rather than executed for his involvement in the plot that cost Jobal his life.

Orlando was an NPC in the completed adventure *All Eyes on Chult*.

## Description

Orlando is a bald human male with a salt-and-pepper goatee and a seemingly permanent frown on his face. His lighter skin tone and accent mark him as being from Amn, even if he dresses as and speaks the language of the native Chultans. He stands tall at 5 feet and 7 inches (1.7 meters) and weighs about 180 pounds (82 kilograms). Not wanting to stick out, Orlando is never really seen outside common and low class clothes.

## History

Orlando was born in Athkatla in 1443 DR to a festhall worker and an unknown father, leading him to a path of petty crime at a very young age. After a few years in poverty however, his life was turned upside down when he was given an opportunity to join the crew of an Amnian trading vessel at thirteen, becoming the captain's ward. For the following decade he learned what he could about stewardship and trade from the ship captain, saving his earnings for when he could attempt to become a legitimate merchant himself. During a long stay in Port Nyanzaru in 1467 DR, the ship captain who'd taken him in fell prey to the machinations of Port Nyanzaru's Zhentarim- leading Orlando to use his earnings to buy a simple shop in the Grand Souk marketplace to build his future.

Unfortunately for Orlando, over a decade of experience as a captain's ward and steward did not translate well to being a local merchant. When his shop, the *Gray Trader* began to fail, Orlando was approached by representatives of the Shadow Thieves, a criminal organization based in Athkatla. Through their patronage, Orlando was able to keep his business afloat, though at the cost of becoming the guild's local fence. Though he turned out to be pretty good at what the guild needed him to do, a return to crime after a decade of hoping to be a rich merchant in the prosperous Amnian colony caused his mood to sour for years to come.

In 1474 DR, his life took an unexpected turn when a short dalliance with a half-drow thief named Jythera resulted in the birth of his daughter Sana. Although Sana kept the strange pair together for a while, Jythera would go on to join an adventuring party intending explore ancient tombs further inland. Like most adventurers to attempt such an expedition, Jythera never returned. Orlando was left to raise his half-elf daughter alone in Port Nyanzaru, and although he did love her, his own strange childhood didn't translate very well to being a sole parent.

When Port Nyanzaru gained its independence from Amn in 1482 DR, Orlando broke his ties with the Shadow Thieves of Amn, becoming an independent fence working alongside a few trusted contacts he'd made during his stay in Chult. This changed in 1490 DR, when a rogue Zhentarim Viper named Florina DuRaal coerced him into working with her and her partner Red-Eye- threatening to harm his teenage daughter Sana if he didn't comply. This brief and stressful business relationship ended when a group of adventurers aligned with the Harpers were tasked with capturing DuRaal and Orlando so they could be questioned. While DuRaal was sent to the Harpers of Waterdeep for questioning and Red-Eye was slain during an attempt to replace the Merchant Prince Jobal with a intellect devourer, Orlando's punishment was being pressed into service of Prince Jobal and losing the *Gray Trader*.