|“||All aboard to the Hinterlands and some other less exciting places!||”|
— The Trolleyman
Not much is known about the Trolleyman other than the fact that he is kind and courteous to the Baudelaires and other passengers that use the trolley as a means of transportation.
In "The Bad Beginning: Part One," the Baudelaires ride the trolley to Briny Beach. The conductor asks if they would like to go to a more pleasant destination because of the clouds skies, but Violet politely insisted on getting dropped off there. He later takes her, her younger siblings, and Justice Strauss into town so that the latter can help the kids pick up ingredients to prepare dinner for Count Olaf.
In "The Ersatz Elevator: Part One," Olivia Caliban took the trolley to the city from Prufrock Preparatory School to visit Mulctuary Money Management. However, while Olivia tried to yell at the trolleyman to stop the vehicle so she could get back on, he ignored her and drove the trolley forward instead.
In "The Slippery Slope: Part Two," he was seen in a flashback driving Quigley Quagmire around locations where his siblings were reportedly held captive, including Prufrock Prep., 667 Dark Avenue , and the other dangerous places such as the Hinterlands.
In "The Penultimate Peril: Part One" he was seen again in a flashback, but this time, he was driving Justice Strauss around every location the Baudelaires had been to in an attempt to track them down, ranging from Lousy Lane to Mortmain Mountains.
In "The End," it was confirmed that the trolleyman survived the Hotel Denouement Fire since he was still operating the trolley at the time Beatrice Baudelaire II took the trolley to the Hotel Denouement. Given that the structure burned down years ago, he was surprised that she made that request. The little girl insisted on going there anyway to find her uncle so despite his reservations, the trolleyman ended up complying with her desire.