Miles Hollingsworth III is a sophomore (Grade 10) at Degrassi Community School. He's preternaturally good-looking and appears to be nothing more than a typical rich bad boy and considered to be "The Man", but looks can be deceiving. Miles is just a teenager looking for love and acceptance, especially from his father, Mr. Hollingsworth II, after being kicked out of boarding school. His father is a popular businessman running for mayor, but won't let his reckless son get in the way. He often verbally abuses Miles who, in turn, acts out in rebellious ways as a result.
He has been long time best friends with Winston Chu, whom he calls "Chewy", and good friends with Tristan Milligan, and Mike Dallas. He was also a good friend of Maya Matlin and developed a crush on her before starting a relationship with her. He has a younger sister and brother, a set of twins, named Frankie and Hunter. He is now on good terms with Zoe Rivas. He was rivals with Zig Novak and seemed to have a dislike towards Drew Torres, however, it appears they are now on good terms. He is labelled as "Billionaire Bad Boy."
He is portrayed by Eric Osborne.