He is amongst the most sinister Disney villains, part by his actions and his pleasure in torturing children for wealth. However, he could also be considered to be moralistic in his own dark and twisted way, as he teaches the boys a pricey lesson for prolonged misbehavior.
Like most Disney villains, the Coachman is sadistic, enjoying other people's pain and is also very cruel whipping his minions and also selling young boys that come to his island into slavery so that he can make money off of them. He enjoys their pain and justifies his action by claiming their slavery as payment for their ill behavior displayed on Pleasure Island. However, it can be assumed he does this for pleasure rather than to teach them a lesson.
The Coachman is first seen sitting at a table in the bar of The Red Lobster with Foulfellow and Gideon. He puffs quietly on his pipe, listening quietly and intently as Honest John proudly recalls selling Pinocchio to Stromboli. The fox then produces a small bag of gold coins - Stromboli's payment - as proof of his success and inquires about the Coachman's business. The Coachman gets the attention of the two when he places a huge bag of gold coins, promising them "some real money" if they help him. He tells the fox and cat that he is collecting "stupid little boys" to take to Pleasure Island. Foulfellow is frightened at the mention of Pleasure Island, and he and Gideon jump in terror when the Coachman gleefully laughs about his wicked business. He tells the two crooks to meet him with any "good prospects" they find at the crossroads of the village, where he will be waiting with his stagecoach, which is pulled by six donkeys; he promises to pay them well. Foulfellow and Gideon end up taking to the Coachman Pinocchio (who has just escaped Stromboli). Jiminy Cricket, fearing for Pinocchio's safety, stows away aboard the coach, unnoticed either by the Coachman or his passengers.
The Coachman takes the coachload of boys, including Pinocchio and Lampwick, to a ferry bound for Pleasure Island, a naughty boys' paradise, where the boys are free to run riot without fear of reprimand from adults or mature teenagers until they turn into donkeys for the Coachman to sell into slavery. The Coachman whips his minions, ordering them to shut the gates, trapping the boys on the island. Later that night, Jiminy Cricket finds the Coachman's minions loading crates of donkeys onto boats. The Coachman examines every donkey, first checking that it can no longer talk by asking its name, then, if the response is a bray, ripping off the creature's clothes if it has any on before his minions throw the animals into crates. One donkey, Alexander, can still talk, and cries to be allowed to go home. The Coachman throws Alexander into a pen of donkeys that likewise can still talk. These donkeys are presumably kept by the Coachman until they finally lose their voices.
At this point, Jiminy realizes the fate of Pleasure Island's visitors and rushes to warn Pinocchio. Though Lampwick is transformed into a donkey, Pinocchio, despite growing donkey ears and a tail, manages to escape the island with Jiminy's help. After that, the Coachman is not seen again.
The Coachman appears in this live action spin-off. In this iteration, however he is called The Ringleader and is much younger, agile and slightly less menacing, yet none the less dangerous, being portrayed by Usher. He and his henchmen charm and encourage the boys into acting like "Jackasses", using his songs and showmanship to mesmerize and coax them onto the rollercoaster, which is stated as the factor that turns boys into donkeys.
20 years ago, his days of turning boys into donkeys were over. He was imprisoned in the Isle of Lost, where he works as a taxi driver. His taxi is a chariot with regular donkeys. But before imprisonment, he spend a year as punishment trying to find all the children he turned into donkeys.
The Coachman did get his comeuppance in the SNES Pinocchio video game, where Pinocchio kicks him down a cliff.
In one crossover comic, Mickey Mouse was washed on the shores of Pleasure Island after a storm. The amusement park had fallen into disrepair, and Mickey noted that it seemed to have been abandoned for a long time. This might hint that the Coachman did, indeed, meet his demise at some point, which is further supported by his not appearing amongst the many Disney villains who meet up earlier in the story.
The Coachman might not be human. Some possible hints at this being the demonic face he makes when revealing his plan, his shadowy minions who may not be human either and the fact that he has four fingers on each hand while every other human character has five. The Coachman could very well be a demon in disguise or at least has access to magic since he is clearly responsible for the transformation of all the boys who went to Pleasure Island. In one concept art of him, he reveals his true face by removing a mask of a fake face. This "true face" of his strongly resembled Stromboli. Coincidentally, both antagonized Pinocchio shared the same voice actor and they lost Pinocchio.
In an annotated English edition of the original novel PINOCCHIO, the Coachman has been compared to Mephistopheles, the demon prince in the classic tale of Dr. Faustus. His boy victims, like Faustus, in effect sell their souls to the Coachman for a life of unlicensed pleasure and, like the devil, the Coachman is there at the end to foreclose the deal.
The Coachman may be the only English character on Pinocchio, speaking in a cockney accent.
The Coachman is the first British-sounding Disney villain.
In the original Italian story of Pinocchio by Carlo Collodi, the Coachman was usually referred to as "The Little Buttery Man" ("L'Omino del Burro"), and he actually drove a large wagon instead of a coach. He was also described as a fat little man who resembled a walking butterball (hence his name), with a small round face like an orange, a red cherry-like nose, and a mouth that was always smiling sweetly. He spoke in a soft, purring voice "like a cat trying to ingratiate itself into its' owner's good graces." He also was rather effeminate in manner, clucking like a mother hen and addressing his prospective young passengers as "my dears" and "my darlings". Yet for all that he was even more sadistic than his Disney counterpart, as displayed when he bites one of his boy-turned-donkeys' ears off while pretending to kiss him.
In the final movie, The Coachman never notices Pinocchio's escape, but in some adaptations and scrapped ideas he sends his minion to chase them. This idea was later used in the Pinocchio videogame.
Also there was a deleted scene where the Coachman hires Honest John and Gideon one last time to bring Pinocchio back to him so that "the law doesn't learn of their business".