Boston has been working on the Toontown Mountain Railroad for as long as he could remember. Like his brother, Boston was in charge of the railroad. One day, Brandon and his friends were hired by him to help around the trainyard. However, Brandon was more interested in the supply of root beer Boston kept in the building behind him. As Brandon walked over to said supply, he said that the job would cost Boston $100. Boston protested that the cost was ridiculous. Brandon commented, "So is the job." After that, Boston granted Brandon permission to the root beer, to which Brandon gladly accepted. While Brandon looked out the window, a pair of eyes appeared right in front of him, startling him. Boston explained that it was just a helicopter named Humphrey. Boston had Humphrey on loan from Sodor along with six of the Skarloey Railway engines (Skarloey, Rheneas, Sir Handel, Peter Sam, Rusty the Diesel, and Duncan the Rock-N'-Roll Engine, although the aforementioned engines never actually appeared on-screen). Boston also said they work for peanuts. Later, after Brandon and his pals got their money, Boston offered them a full-time job on the railway, which they declined.Later in the Dave Felis vs. Sly Cooper Trilogy, Boston was discovered to have sold the railroad to a company called Mega Toon Industries. The heroes arrived at Boston's office to interrogate him. The heroes used a vat of dip to interrogate Boston into telling the truth. Boston revealed that he had a chance to sell the railroad, but Mega Toon wouldn't buy it unless Annie May sold them hers. "The stubborn witch wouldn't sell," Boston said. Boston also revealed that he made the heroes take pictures of Annie May to blackmail her and admitted it was a lousy thing to do. He also said that he had worked on the railroad his whole life and didn't want to see it destroyed. The heroes asked why and he said, "If I tell you, I'm as good as dipped!" Ryan threatened that Boston would be dipped if he didn't tell them. In Boston's final words, he said, "Unless Annie May's will shows up by midnight tonight, the railroad's gonna be land for a freew--" but an unseen assissin squirted Boston with dip before he could finish. The assassin nearly got the heroes as well, had they not dodged the squirt right away. As for Boston, he screamed in agony as he melted into a smear of paint in the puddle of dip he was squirted with. He kept melting until every last bit of him (literally, EVERY last bit of him) was nothing but a smear of paint, including the very base platform he stood on.
Boston is strict, arrogant, unreasonable, slightly greedy, nervous, sarcastic, and short-tempered. He cares very deeply about the railroad, for he did not wish to see it destroyed and was willing to go to great lengths to keep it intact. Like all toons, he fears the dip more than anything (besides Dragozaurs, for they creep him out for having been CGI-rendered.)