Pickup trucks today are more popular than ever before. They now come feature packed with many creature comforts which in some cases also rival luxury SUVs. But at its very core, the pickup is a work vehicle and its contribution to modern society cannot be quantified. You can certainly credit these workhorses with building entire nations.

Legacy Classic Trucks, based out of Jackson Hole in Wyoming is now engaged in bringing back and retelling stories of old-school American trucks. They specialize in restoring and injecting a new lease of life into these vintage pickups, in their own unique way. I recently had the chance to interview founder Winslow Bent to find out more.

A post shared by Legacy Classic Trucks (@legacyclassictrucks)

Meet Winslow Bent, originally a native of Chicago, Illinois. Growing up, Winslow was surrounded by heavy machinery, as his Dad owned a stainless steel fabrication plant that made giant blenders and mixers. Consequently, right from an early age, Winslow was just as interested in cars. He was the founder of the Classic Car Club back at his High School. He eventually got into drag racing and even Formula Ford as well. But it wasn’t until he moved to Colorado to go to University did he really become interested and grow a strong affinity towards pickup trucks.

Also, having been on countless Overlanding expeditions around the world, be it in Africa, South America, or South East Asia, Winslow became a traveler and adventurer through and through. He spoke about the time when he circumnavigated Australia in an old 1974 Ford Falcon that he bought for just $300. In ’04, he took a bone stock 1989 from Jackson Hole up to Alaska. From there, he drove south and over the course of six months, eventually ending up in Panama City, touching close to a dozen countries en route.

Aside from that, he’s also done countless trips across the U.S., and if there’s an event surrounding trucks and off-roading, or rock crawling he’s probably already done it. This is important because his vast experience in the field actually gives him an idea of what exactly could one of his potential clients be looking for.

Right around 2008, Winslow noticed that upon visiting any car show, the Concourse Class cars like your vintage Ferrari or Mercedes took center stage, while trucks weren’t really getting the kind of attention that they really deserved. He also noted that the workmanship on these pickups just wasn’t up to the mark or at the level that he would like.

Okay, so it became obvious that restoring some sort of off-road vehicle had potential and one of Winslow’s favorite names was the Toyota Land Cruiser. However, there were already a couple of well-established names like Icon Trucks, and Proffitts’s Cruisers, already working on restoring Land Cruisers. But when it came to the restoration of old-school American trucks, there was a huge hole in the market. This truly was a definitive moment in the firm’s history.

Around the same time, shopping around for old cars also gave him an idea about how he’d want to operate a restoration shop and so with a gap in the market for old-school pickups, Winslow set up Legacy Classic Trucks in 2008.

The plan was to get started with vintage pickups ranging from anywhere between 1920 and 1970. Now unlike before, Winslow was going to pay a great amount of attention to how these things were restored and put together. He wanted to do it right to the teeth and ensure that things don’t fall apart once a customer drives off the shop floor.

Now initially, the demand for these trucks was pretty low given that not many people knew what the product really was. Winslow in fact had to finance the first few builds himself, in order to get the ball rolling. But getting one of the early builds, which was an old Dodge Power Wagon in front of an audience at the 2012 SEMA show in Vegas. Legacy ended up taking a Top Three in the show and put them on everyone’s radar.

To cater to the truck enthusiast, the range of restoration services at Legacy is obviosuly quite extensive. They follow what’s called a 3 Stage Restoration Process

Now, if you don’t really know what you’re looking for, depending on how you intend to use your truck, Legacy will suggest and design a vehicle around you. For example, are you looking at towing, rock crawling, or hitting the Moab desert or something to cruise around town because those are completely different vehicles. So based on your preferences, Legacy will figure out if a gas or diesel, a stick shift or automatic suits you, and what you essentially end up with is a build sheet.

Also, one of the things that make Legacy unique is that they’ll be able to give you an accurate quote of how much the build is going to cost you unless of course, a customer at a later point decides to add more stuff. This is a practice that Winslow adopted from his father’s fabrication business. This distinguishing factor is certainly something that Legacy customers truly appreciate.

According to Winslow, restoring cars was not an easy business and margins are super thin. So you want to get everything right the first time because if you don’t that margin is gone. Anyone could plonk a big old crate engine with 700+ horsepower under the hood and call it a day, but you won’t be crossing a mountain pass with your renewed rig. Legacy knows this stuff inside out.

Also, Winslow goes the extra mile and personally puts a customer vehicle through its paces before handing it over. That really is the ultimate stamp of approval. For instance, he takes customer cars on a treacherous mountain pass close to the shop to see how these trucks perform in the real world. A 500-mile run-in, the first oil change, the first car wash, it’s already done and dusted to ensure that you don’t end up with any untoward surprises later on.

Legacy Classic Trucks owes a big part of its success to the Dodge Power Wagon. Their focus on restoring old Power Wagon’s is what put them on the map. Now, with any restoration build, the costs could be astronomical and the same was true for the Power Wagon. Winslow felt that demand really wouldn’t be that strong for such a vehicle, but he was totally wrong.

Legacy offers these Power Wagons with a Regular Cab (that came from the factory) or as a crew cab or extended cab (built in-house by Legacy). According to Winslow, it was the four-door models that really captured people’s imagination. Given how good the demand was for these builds, Winslow was able to scale things and do considerable R&D to further fine-tune their final product.

These vehicles were primarily working trucks back in the day, parts like the bed are generally so smashed up, that it makes no sense to restore them. Instead, Legacy took a different approach to put the necessary tooling together to build beds, running boards, and fenders, all made in Detroit, Michigan, right here in the U.S.A. In the end, scaling things allowed the 12-member team at Legacy to put together a far more reliable vehicle, which wouldn’t have been possible if this was just a one-off build.

Winslow also touched upon the rich history and heritage that surrounds the Power Wagon. For instance, Dodge’s idea of putting together a 1-Ton truck along with four-wheel drive and its role in moving troops and supplies to the front lines during World War II, really proved its capability.

The Power Wagon earned a reputation for being tough, frugal, and reliable. Henceforth, a Civilian version was also built and it saw action in other avenues, be it with oil exploration in the middle east or traversing the mountain passes of Northern India, Burma, and South East Asia. In fact, the Power Wagon was being built to serve these markets up until the early 70s.

Back in the United States, the Power Wagon also played a big role after the war in the expansion of the great American West. Be it dams, bridges, power lines, forestry, mining, or utilities - this tough-as-nails truck was there. Up until the 50s people mostly relied on the railroad for supplies and you’d find most American cities around one. However, trucks made it possible to get to some of the more remote locations, helping to build infrastructure.

Riding on the success of the Power Wagon, (close to a third of Legacy’s overall builds so far) people eventually started showing up with vehicles of various other makes and models. Think Studebakers, Hudsons, Diamond T, Mack, old Land Cruisers, Fords. Legacy also does Jeep Scrambler conversions and the Legacy Chevy Napco.

A couple of years ago, the National Parks Service, which is a government organization, contacted Winslow and wanted to hire him as a consultant to go over their fleet of 33 historic buses from the 1930s. Well, Legacy gave a few suggestions and ideas including restoring them back and maybe even employing a hybrid powertrain.

And before they knew it, Legacy was suddenly now in the business of restoring vintage buses as well. Obviously, word got out and several other national parks from across the country, including Yellowstone, Zion, and Grand Canyon National Park also got in touch with Winslow to restore their fleets as well. These buses have lower emissions and the regenerative braking that they make use of, helps to cut back on asbestos dust in the National Parks.

These buses can only be pulled off the line in the winter because they’re used extensively during the summer months. So Legacy ends up spending a good chunk of the winter restoring these old buses and come summer it’s back to the old school trucks. Winslow told me that working on these buses isn’t easy because aside from steel, they’ve also got to deal with materials like wood and aluminum.

Finally, I had to touch upon the EV revolution that is currently underway across the auto industry. I wanted to know if that is a route that Legacy was looking to take. Sure enough, Winslow is totally into it. But for the moment, apart from the supply chain issues, main-stream manufacturers have preference first. The infrastructure is also still not there yet.

To sum it up, Legacy Classic Trucks have managed to capture the essence of old-school Americana with these Vintage pickups by modernizing them but retaining their soul. Obviously, their appeal is second to none. The 115 examples of the Power Wagon sold so far to clients all around the world is proof of that and, if you want one, be ready to get on the waitlist.

1937 Mount Rainier Kenworth Tour Bus by Legacy Classic Trucks

1956 Custom 1942 Dodge Power Wagon Shows Up in Jay Leno’s Garage