Texan Rick Bailey Is All-In On Drag Racing

As Lil Gangster and the broader mix of 5.30 index racing continues drawing packed fields and some of the best side-by-side action in sportsman drag racing, more racers known for high-horsepower headline acts are going to the fray or finding room for a second car built to have some simple fun in the class. Rick Bailey is one of them.

While his name has become increasingly associated with Pro Mods, fast no-time and Pro 275 cars through his partnership with Corey and Justin Swanstrom and Todd Fullone, Bailey’s newest project is a back-to-basics 1955 Chevrolet built specifically to join one of drag racing’s fastest-growing categories.

Bailey’s recent rise in the sport has been anything but gradual. After spending roughly 25 years away from racing while raising a family and building a career, he jumped back in seven or eight years ago with a twin-turbo Nova known as “Sherman,” followed by a turbocharged ’69 Camaro that he called “Bandito.” Today, his stable includes a blown ’67 Mustang campaigned in no-time and Pro 275 competition, a bold purple Pro Modified Camaro “Draco,” a new Pro 275 Nova that’s under construction, and now the yellow Tri-Five that offers shades of the hot rods of yesteryear.

“We’re all in,” Bailey says of his new racing addiction. “I watched my kids grow up through football and softball, I made my career, and said, ‘Now it’s time for me to have some fun.’”

Ironically, the 5.30 Chevy came from much closer to home. The car belonged to Bailey’s crew chief, Orlando “Orly” Kano, who campaigned it as a slower index car before Bailey traded a Factory Five ’33 Ford Roadster for it. Looking at the growing participation in 5.30 racing, the idea for what to do with the pieces came together quickly.

“I had the motor out of my Monte Carlo just sitting there,” Bailey explains. “It’s a 585 making around 1,100 horsepower naturally aspirated, so I said, ‘Let’s drop it in the ‘55, put a Powerglide behind it, and go Lil Gangster racing.’”Rather than chasing the quickest numbers — the car ought to run the fours if he tried — Bailey is building the combination to comfortably run under the index before pulling power out electronically. A nitrous controller operating the transmission’s dump valve, timing management through the ignition grid, and careful launch tuning should allow the classic Chevy to repeatedly click off competitive 5.30 passes while keeping some in reserve.

Everywhere Bailey races, he sees the appeal of this evolving category. “They pay just as much, or more, for the 5.30 stuff,” he says. “I don’t care if it’s me, Tyler, Orly, or somebody else driving it. Let’s just take another car and have fun.”

The project also fits neatly alongside Bailey’s growing relationship with Swanstrom’s program. While his long-term plans still include the Radial Outlaws Pro 275 championship hunt and potentially returning Draco to big-tire Pro Mod racing, the yellow Chevy gives the team another reason to hit the road together.

“I think me, Justin, Todd…we’re going to have a swarm of Lil Gangster cars, eventually,” Bailey says with a laugh. “It’s great racing, great media content, and it’s just fun.”Bailey expects the ’55 to debut at Swanfest before joining an already crowded schedule.

For a racer who has gone all-in on drag racing and is making up for lost time, adding one more car means just one more opportunity to make another pass.