teve Caballero is one of the simplest, yet most complex humans on the planet. On the one hand, he’s quite possibly the nicest man you’ll ever meet. He wants to hear your story, wants to know about your life and what excites you, and he’s as enthusiastic and thankful for any opportunity to go on a ride or play with a bike as his fans are to get a picture with him. He carries himself with a meekness and an attitude of gratitude, which is maybe why he comes off as so unassuming. On three separate occasions during our weekend together, someone would approach us on behalf of someone else who’d recognized him but was too nervous to say hello and, each time, that person walked directly to me to ask for an autograph (because the tattooed dude with the white hair must be the pro skater), only to be shocked it was the little white-bearded guy next to me who they were really after.

Steve Caballero Indian
Cab explaining how much higher the bars on his bike feel compared to the stock onesZach Cohen

The thing is, that gentle kindness doesn't transfer into how Cab pursues his passions. No, the man Thrasher Magazine named "The Skater Of The Century" in 1999 may be quiet and kind, but the 52-year-old renaissance man is about as passionate and ruthlessly dedicated to succeeding as they get.

Cab started skating in 1976 at 12, started skating in competitions at 14, and turned pro by 15. He invented tricks like the full Cab (yes, named after him) and half Cab (which VANS named a shoe after) and is credited with inventing the frontside boardslide. He and Tony Hawk, three years his junior, are seen as the major pioneers of half-pipe skating (he'll tell you that Tony is the best ambassador for any sport ever and that he's thankful Tony is the one who got "famous"). He set the record for the highest air out of a half pipe in 1987 at 11 feet—a record that stood for a full decade—and he has the record for the longest boardslide on a 44-step handrail.

Steve Caballero Indian
Getting ready for Cab's maiden voyage on his custom Indian Scout BobberZach Cohen

He also loves music, and has played in a number of punk bands over the years including The Faction, Odd Man Out, Shovelhead, and Soda. He’s toured all over the world with his bands and played some pretty incredible shows with other amazing bands.

But if you really want to get Cab excited, all you have to do is bring up motorcycles. As a kid in the `70s, Cab was a huge fan of Evel Knievel. He bought his first bike at 15 after turning pro, a Honda MB5, before getting bit by the sportbike bug, buying a 1988 Kawasaki Ninja 250 and then a 1990 Honda CBR600RR.

Cab quickly realized sportbikes would kill him, and he got into vintage bikes and bobbers in the early `90s, buying a '63 BSA Lightning 650, a '73 Norton Commando 750 and '74 Commando 850, and a 1959 Ariel Square Four. He's added to the collection since then, including the 1944 Harley-Davidson Flathead Mel Stultz was using on the Wall of Death at the Born Free Motorcycle Show and a 1952 Pre-Unit Triumph he built with Bryan Thompson for Born Free 8.

Steve Caballero Indian
Looking for troubleZach Cohen

Most recently, Cab has been flat track racing. His first experience came at The Race Of Gentlemen, where he raced the 1944 Flathead after learning to ride it on a dirt track just two days before the race. Since then, he can often be found at Costa Mesa Speedway on Harley Night spinning laps, and Roland Sands has been pushing him into Hooligan racing.

Despite telling Rolling Stone Magazine that he was done building bikes at the beginning of this year, an opportunity came along with Indian Motorcycles to build a custom Indian Scout Bobber for the Brooklyn Invitational in New York. Cab, who's always had a soft spot for Indians (his Pre-Unit Triumph pulls style influences from the first Scout), was up to the task with help from Sands.

With only three weeks to get the bike in shape for the show, the build relies heavily on parts from Roland Sands Design. You could call it lazy (though not with such a short timeline), but I call it good for the consumer (because unlike the other builds, you can get basically the same setup). The trickiest parts will be the move to 19-inch wheels front and back, something I’m not sure I would recommend unless you planned on spending some time on the dirt track.

Steve Caballero Indian
Cab did a great job of keeping the bike's DNA while improving it across the boardZach Cohen

Custom Bits:

  • The gas tank was narrowed by six inches
  • RSD Track stainless steel 2-into-1 prototype exhaust
  • RSD hand fabricated number plates
  • Wheels: Indian-spoked hubs re-laced with Excel 19-inch wheels
  • Custom Ferrari-inspired paint by Specialized Coatings
  • Custom pinstriping by 12k Gold Leaf Work

Parts You Can Buy:

  • RSD Enzo solo seat
  • RSD steel esh radiator guard
  • RSD front belt guard
  • RSD pulley cover
  • RSD rear belt guard
  • RSD traction grips
  • RSD radial master cylinder
  • RSD radial cable clutch perch and lever
  • RSD mid controls
  • RSD pullback riser
  • RSD gauge relocator
  • RSD tracker fork brace
  • RSD vertical shock mount
  • Dunlop DT3 flat track race tire (130/80-19 front and 140/80-19 rear)
  • Barnett cables and clutches
  • Renthal Fatbar handlebar
  • 12.0-in Progressive Suspension 970 Series reservoir shocks
Steve Caballero Indian
Choose your flavorZach Cohen

We spent the better part of the afternoon after the show terrorizing Brooklyn, with Cab riding his custom Bobber and me on a stock Indian Scout Bobber. While the DNA of the original Bobber is very present in Cab’s build, the modifications he and Sands made make for big improvements.

The first thing you notice about the bike—at least when it's running—is the sound. That exhaust is LOUD, something Cab likes to remind you of every few seconds as opens up the motor or blips the throttle while slowing or waiting at a light.

Steve Caballero Indian
Like a kid with a freshly opened birthday presentZach Cohen

The increased ride height and upgraded shocks and exhaust (and new tune) are the biggest performance upgrades on the bike. The shocks do wonders for keeping the bike from bottoming out, something Cab found incredibly beneficial on the beat-up Brooklyn Streets, while the freer flowing exhaust and fuel map wake up the motor impressively.

Overall, I really dug most of the mods Cab and Sands did to the bike. Narrowing the tank made the bike feel lighter and more nimble in between my knees and improved the overall aesthetics of the bike greatly. I found the riding position a little cramped, but I’m also nine inches taller than Cab and the bike wasn’t built with my lanky frame in mind.

Steve Caballero Indian
It's all in the detailsZach Cohen

This was actually the first time I got to experience a true mid control on the Scout platform, and it was everything I hoped it would be. They didn’t have time to make a heat shield for the exhaust, which runs right where you’d naturally put a foot down at a stop, but the sweep of the cans stays out of the way nicely when riding.

The 19-inch wheels keep Cab’s custom Bobber from being the perfect cruiser, but they’ll benefit him greatly when it comes to the track. Unfortunately, his deal with Indian will see the bike on a tour of motorcycle shows for almost a year before he can take possession and start racing with it, but we’ll check back with him then on how he and the bike are doing.

Steve Caballero Indian
The sound of Cab's bike as it echoed through the tunnels was deafeningZach Cohen
Steve Caballero Indian
Cab and his custom Indian Scout BobberZach Cohen
Steve Caballero Indian
Enjoying the last of a perfect day seeing the city the best way we know howZach Cohen