Steve Caballero: A Skateboarding Pioneer and Inventor of Tricks That Propelled Skateboarding to New Heights

Steve Caballero invented the “caballerial” when he was 15 years old. The trick is done on the vertical and is a fakie 360 ollie. The trick, first landed in 1981 was, and still is, a difficult trick to perform. Here is a video of Caballero teaching the trick: The trick was important because it ushered in a new era of skateboarding that was more technical and athletic. Alan Gelfand invented the ollie in 1978 and it opened up new possibilities on all kinds of terrain. The “caballerial” took it to new levels and its inventor went on to a spectacular career, both as a competitor and vertical pioneer.

Steve Caballero was born in San Jose, Ca. in 1964 and began skateboarding in 1976. After placing 5th place in a contest, Stacey Peralta asked him to join Powell Peralta. He turned pro in 1980. He then began a prolific run in contests that included 31 first place finishes over a twenty year period.

Highlights of this period include inventing the frontside boardslide and setting a then record 44 step rail slide. Here is a clip: In 1987 Caballero soared 11 feet outside of a half pipe. That massive air was a record that stood for nearly a decade. Danny Way broke the record in 1997.

Videos also played a part in the Caballero story. He was a member of the Bones Brigade and appeared in many of their videos including the classic “The Search for Animal Chin.” Caballero was also featured as a character in five of the Tony Hawk Video games.

Caballero is no. 14 on TransWorld Skateboarding’s “Most Influential Skateboarders of All Time.” In 1999 he was named “Skateboarder of the Century” by Thrasher Magazine.

Caballero has been married twice and has three children. He lives in Carlsbad, Ca. and continues to skate. His sponsors include Powell Peralta, Bones Bearings, Independent Truck Co., Bones Wheels, Vans Skate Shoes, Skull Candy Headphones, Ohana Boardshop and Protec Helmets.