Sydney to the Max Wiki

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Leonard "Leo" Lawrence Webb is a main character in the Disney Channel original series, Sydney to the Max. He is the best friend and later cousin-in-law of Max Reynolds from the '90s; they are still friends in the present-day. He is also the cousin of Max's late wife Alisha.

He is portrayed by Christian J. Simon as a boy, and Winston A. Marshall as an adult.


Leo is really dedicated to whatever he is doing and is an overall dedicated person. He gives everything his all. He likes to "play it safe" and constantly tried to keep Young Max from doing something that they could get in trouble for.


Leo has black hair and brown eyes. His hair poofs up a little bit at the top of his head.


  • He is Max's friend from the 1990s.
  • He always has Max's back.
  • In the '90s, his dad owned an arcade called Just Fun and Games. Both Leo and Max worked there. It is currently unknown if his dad still owns it now.
  • His present self made his debut in “As Bad As She Gets”.
  • His adult self has a son named Leo Jr., who is more commonly called LJ.
  • It is unknown if he is divorced or widowed.
  • Leo and Max kept in touch only occasionally after high school.
  • He sees Judy Reynolds as a second mom.
  • He sees the Dog Boys as the “Wolf Guys” since the name has more “pizzazz”.
  • He runs a tech company. It is implied that this is a gaming company. It is a dancing app.
  • As an adult, he thought about moving back to Portland and opening an office.
  • He once rented a houseboat.
  • His parents wanted him to attend a private school called Laramie Academy, which was a place for gifted and talented people. He never went as the place burned down during its winter break.
  • Leo is very successful and wealthy in his dancing app in San Francisco.
  • His dad makes an appearance in Slurping with the Enemy.
  • As revealed in "Thirteen Candles", his cousin Alisha is Max's late wife.
  • In Do the Write Thing it’s revealed Leo himself has faced discrimination because of the color of his skin.
  • Leo along with Olive are the only main characters to be absent in some episodes.


To view the Leo Webb gallery, click here.