Simon

Simon
Simon is an automated construct approximately 3 feet tall, wearing a jester outfit and holding a small pinstriped cane as a club. He does not speak, answering questions instead with gestures and nods. He is also capable of shooting darts.

In the Ravenloft module,[1] the duchess Lady Dilisnya commissioned the mad toymaker Frtiz von Weerg to build a clockwork copy of her jester, Pidlwick. Pidlwick entertained Sergei and Tatyana whenever she visited Ravenloft, and the toy (named Pidlwick II) was meant as a gift to them. However, Pidlwick II murdered his predecessor, and Strahd decided to keep the toy around out of amusement.

In DCA, the toy is recovered from the treasure wagon of evil Vistani, rolled up inside a unicorn run. Although he was meant as a reward to the Crew for rescuing Arabelle, it befriends the girl instead and goes with her to search for the missing hag pin that Arabelle fears will be used to murder her. In DCA, Simon has two types of darts--a sleep dart (orange stripes), and a poison dart (green stripes) that does 7d6 poison damage in addition to piercing damage--which it can shoot from its mouth. The construct does indeed kill a child in the Vistani camp when it and Arabelle are suddenly confronted. Although the Crew do not see this, the players afterwards refer to Simon as "murderbot".

Trivia (spoilers)

 * Simon initially has it out for Diath because he was the one to murder Arabelle. Likewise, Diath is the least friendly towards Simon, cheering when the initial incarnation was crushed by an earth elemental.
 * When Simon tracked the Crew down and confronted them outside Barovia, Paultin was able to charm it and command it to be friendly to the Crew. He and Evelyn proceeded to praise and coddle it, and later referred to it as their "son". Simon stayed friendly and followed the Crew's commands even after the spell wore off.
 * Nate gave Simon its name seemingly spontaneously in the middle of episode 36, and the name stuck.
 * Chris revealed that when Simon disobeyed Paultin's orders to flee and decided to help defend him from the yakfolk (shortly before he was crushed), he gained a soul.[2] The next version of Simon they recovered also developed a soul, as it appeared inside the Soulmonger after Strix accidentally charred him.
 * Evelyn brought Simon's parts to a dwarf smith and asked for him to be put back together. Instead, Master Flamebane built a life-sized model of Evelyn using those parts, which she was mysteriously resurrected into after she died the first time.
 * When the Crew traveled to the past, they found that Lady Dilisnya intended to use Pidlwick II to kill Tatyana to prevent her wedding to Sergei from taking place. Paultin and Evelyn instead instructed the construct to behave and carried it along with them, happy to have their son back.
 * Paultin has built a small portable keg for Simon to carry on his back, from which Paultin can sip wine through a straw.
 * When Paultin returned the hand and Chalice to the Raven Queen due to his his "fate" being "stolen", her consolation prize to him was to make Simon's mouth able to speak instead of shoot darts. Simon proceeded to tell jokes and called the Crew "Papa Paultin", "Mama Evelyn", "Auntie Strix" and "Uncle Diath". Unfortunately, one of Strix's fireballs bounced back onto the Crew and incinerated Simon. Evelyn saw Simon appear inside the Soul Monger, implying he had a soul. Omin was later able to cast 'raise dead' and bring Simon back to life, but with his mouth back to the way it originally was.
 * In an episode of Nate's other show, 'Dark and Dicey', Paultin made a guest appearance. When Anya asked if his son would like to join her cult, Paultin said that he thinks Simon is already starting one of his own, possibly referring the the friendly children he met at the Yawning Portal.[3] In episode 123, Simon was dragged away during the Crew's visit to the Cassalanter mansion and charmed into nearly joining an Asmodeus cult, until Paultin intervened.
 * After the Crew were given a mansion to stay in by Magnus Burnsides, Simon began living in the turret. He was noted to be bringing cookies and milk up there, and later it was revealed that he had lured a child into the turret and kept him trapped there. Simon had also drawn pictures of himself as a real boy. As the Crew worried about how to explain the kidnapping without getting Simon in trouble, Simon ran away and almost got himself killed, showing that his depression had grown severe. This was somewhat relieved when the street urchins came to stay at the Waffle House and kept him company, with Nat teaching him sign language.
 * Ulkoria Stonemarrow polymorphed Simon into a human child, still wearing his jester clothes. He no longer acted cute or told jokes, but rather spoke to the Crew on a first-name basis and seriously discussed with the other children the possibility of them leaving to start their own adventuring party. He admitted that he needed some help learning how to be a real boy, "a 90-something year old boy".[4] He showed some displeasure at the thought of eating nothing but pies at the Waffle House, and of eventually growing old and dying. Simon also expressed his frustration with the Crew for trying to hide each couple's feelings for one another. Chris elaborated, "Simon has been observing the #Wafflecrew for a while now. He has also picked up a few of [their] bad habits".[5]Although he told Paultin that he idolized him and wanted to become a bard to entertain people and take their minds off their wretched lives, Chris also described him as having a mischievous glint in his eye. He later begged Paultin to let him join the circus after he watched performers play with whips lit on fire, but as Simon was only allowed to clean the animal pens, he quit after a few days. On a trip to the beach, he built a sand castle in the shape of Ravenloft, and told Paultin he missed it and wondered when they'd go back. He also told his parents that he now wants to grow up to be a pirate.