Chevy Silverado Trail Boss earns its name, reputation

Chevrolet used to have a saying, “Like a Rock.” While they’ve discontinued that advertising campaign, I might suggest they resurrect it with a slight modification: “Chevy: Like a Boss.” A Trail Boss, that is. This week’s tester was the 2020 Chevy Silverado Custom Trail Boss.

This full-size truck is not just aesthetically interesting, it’s actually pretty interesting to learn about some of its specifications. One fact that surprised me was the combined Custom Trail Boss and LT Trail Boss account for about 20 percent of all Silverado sales.

In all my years of driving vehicles, I had never been behind the wheel of a Trail Boss. I rather enjoy this type of truck that looks to expand the consumer base by offering off-road appeal plus on-the-road power.

In the past I’ve written about my love of the Ford Raptor. While the Trail Boss doesn’t necessarily compete head to head with the Raptor, it’s in that same arena.

On looks, the Silverado Custom Trail Boss has a totally different look than the standard Silverado. My tester had a black exterior and a corresponding blacked-out grille and black bumpers. The posture alone is impressive with a two-inch lift, skid plates, off-road shocks and off-road tires. If you like trucks that look tough and rugged, then the Trail Boss would not disappoint. It certainly stands tall and big, and it drives just as big.

Performance-wise, this truck lives up to its name as it is a boss on and off the road. Although I did not take this truck off-road, it certainly was ready and prepared to do so. Chevy gives the Trail Boss its biggest gasoline engine as it’s mated with a 6.2-liter V8 and 10-speed automatic transmission. As such, it cranks out 420 horsepower and 460 lbs.-ft. of torque. The Z71 off-road package includes the aforementioned two-inch lift along with monotube shocks, hill descent control and heavy duty air filter.

There is also an automatic locking rear differential and two-speed transfer case. All of this translates to a Silverado unlike any other I’ve driven. The overall performance may not appeal to every truck buyer, but as the numbers attest (nearly 20 percent), it has broad enough appeal. If you like your truck on the more comfortable and smooth side, then this might not be the right option as the Trail Boss drives big and feels a little more like a monster truck than a regular Silverado.

But I also think that’s the point and intent of this truck. It’s supposed to be different, and it accomplishes that.

Speaking of being different, the interior of the Trail Boss is not necessarily what the trend is for the full-size truck segment. Usually big trucks like the Silverado, Ram and F-150 are lavishly appointed with high-quality touchpoints throughout. Of course, those appointments come with an ever-skyrocketing MSRP, too.

The Silverado Trail Boss is intended to keep the price down but sacrifices some of those higher quality touchpoints. For a truck named Trail Boss that’s intended to get muddy and go off the road, you likely wouldn’t need or expect luxurious touchpoints. More of the minimalist approach is used in the Trail Boss, including cloth seats and rubberized vinyl floor mats (which are needed if you’re getting muddy).

A unique feature is the 40/20/40 front seat, where the big center console can be lifted up and become the back of a third seat in the front. It is kind of a throwback to the old days of bench seats in pickups. That jumper seat even comes with a restraining device for added safety.

The infotainment system is adequate and does its job. Overall, the 7-inch color touchscreen is responsive, but feels a little on the small side, considering the size of the truck.

Another negative is the lack of running boards. This might make it more challenging to get in and out of this lifted truck. Since it’s intended to be used off-road, it could be an engineering issue – running boards would’ve likely affected ground clearance. But certainly, it would’ve been nice to have an easier way to get in and out of this truck.

The starting price of this truck is $39,500. With the 6.2-liter engine added at a cost of $2,400 and a couple of other packages and features, my tester had a final price tag of $45,310, which is significantly less than other Silverado trims and certainly less the Ford Raptor.

The Silverado Trail Boss has a very specific place in the Chevy truck lineup. Having had some seat time, I now understand why it has a growing fan base.

Jimmy Dinsmore is a freelance automotive journalist.


  • Price/As-tested price................................................ $39,500/$45,310
  • Mileage.......................................... 14 mpg/city; 18 mpg/hwy
  • Engine............................................. 6.2-liter V8
  • Horsepower................................. 420 hp/460 lbs.-ft.
  • Transmission................................. 10-speed automatic
  • Drive wheels................ 4-wheel drive
  • Final assembly point................ Roanoke, Virginia

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