Richard Rawlings Ranked This the Biggest Collection Buy of His Career — Its Owner Was a Flat-Track Racer Nicknamed ‘Kannonball’

Gas Monkey Garage ranked its three biggest classic-car collection buys ever, and the winner wasn’t even about the cars. Behind a Minnesota flat-track legend’s life’s work sat a $17.6 million motorcycle empire, a factory-lightweight Coronet, and a story Richard Rawlings refused to let disappear.

The Collection That Made Richard Rawlings Stop Counting Dollars

Richard Rawlings has walked away from a lot of deals with a number attached — $45,000 for a hidden Alabama garage, a seven-figure guess for a Wisconsin property stuffed with more than 200 cars. But when Gas Monkey Garage sat down to rank the three biggest collection buys in the shop’s history, the top spot didn’t go to the biggest number on the table. It went to the life’s work of a Minnesota flat-track racer nobody outside the motorcycle world had ever heard of — a man who spent seventeen years launching himself sideways around dirt ovals and picked up the nickname “Kannonball” for it. By the time Rawlings finished walking through what that racer left behind, the video wasn’t really pitching a car deal anymore. It was making sure a life’s work didn’t just get sold off and forgotten.

The countdown starts smaller. In Good Hope, Alabama, Rawlings talks his way into a hidden garage packed with a ’55 Chevy hardtop, a Chrysler business coupe, an ’84 Corvette, a chopped Chevy, a Dodge, and an original-owner Datsun 280Z, plus a scatter of old Chevy trucks and a Camaro buried under decades of dust. After running the math out loud on camera, he closes the whole lot for $45,000 and trailers six vehicles back to Dallas. It’s the kind of deal Gas Monkey has built a franchise on — but the video treats it as the undercard, not the main event.

What a Factory Lightweight Coronet and a 69-Built ZL1 Are Actually Worth Chasing

The second-ranked buy is where the car talk gets serious. Rawlings and a British transplant on his crew nicknamed “Big Chris” walk a private Wisconsin property holding more than 200 cars — Corvettes, Tri-Five Chevys, a run of Shelbys and Hemi cars, and, tucked into the mix, a factory-lightweight Dodge Coronet. That’s not a casual claim to make about a Coronet. Dodge built only 101 of those cars for the 1965 season, part of a run of roughly 100 Belvederes and Coronets that Chrysler acid-dipped — a euphemism for chemical-milling the sheet metal — to strip more than 60 percent of the wall thickness out of the hood, doors, fenders, and front bumper. Chrysler deleted the heater, radio, carpet, and back seat too, then handed the survivors either a Hurst four-speed or a reverse-pattern automatic with Park removed, backed by an 8¼-inch rear end geared at 4.86:1. Racers like Dick Landy, Ronnie Sox, and Bud Faubel ran them into the low 11-second range in 1965, which was absurd for a car with a factory warranty.

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The same walkthrough turns up talk of the aluminum-block ZL1 Camaro — a car built in numbers so small the whole legend fits in one sentence: Chevrolet produced exactly 69 of them for 1969 through the COPO 9560 order code, after Fred Gibb Chevrolet’s initial order of 50 proved too expensive to move and the remainder scattered across 41 dealers nationwide. A Shelby GT500 KR gets its moment too, the 1968 Mustang that wore Carroll Shelby’s trademarked “King of the Road” badge and hid a 428 Cobra Jet rated at a sandbagged 335 horsepower — real-world output ran well past 400 — good for low-13-second quarters before Ford pulled the model after just one year and a little over 1,200 built. None of these are cars you find by accident. Finding three storylines like that on one property is the reason Rawlings put a million-dollar guess on the whole collection.

What keeps the Wisconsin stop from feeling like just another rich man’s garage is where the video says the collection connects back to Cars Curing Kids, a charity built around exactly this kind of car culture. Rawlings doesn’t treat the property as a pile of assets to flip — he treats it as a story about why someone spent decades accumulating cars that mattered, which sets up the much bigger version of that same idea waiting at the top of the list.

Why the Story Mattered More Than the Sale

Then the video gets to Denny Kannenberg. From 1956 to 1973, Kannenberg raced everything with two wheels — ice races, flat track, the Five States Scrambles Championship — and rode aggressively enough to earn “Kannonball” as a permanent nickname. Off the track, he built a Minnesota business called Sport Wheels into the largest motorcycle wrecking yard in North America, eventually holding more than 7,000 motorcycles. When his collection came to market, Worldwide Auctioneers ran it as a no-reserve sale in Auburn, Indiana, moving 165 largely original motorcycles and roughly 30 collectible vehicles — along with a trove of racing memorabilia — for a combined $17.6 million at a 98-percent sell rate. Gas Monkey Garage presented that sale, and the video’s final chapter walks through pieces of it: rare bikes, a Shelby GT500 KR, and a story about Kannenberg’s life that Rawlings clearly didn’t want to let disappear into a spreadsheet of lot numbers.

That’s the detail viewers latched onto hardest. Long after the hammer falls on a collection like this, most of what made it matter — who built it, why, what it cost them in ice-track crashes and decades of buying and selling wrecked bikes — usually evaporates with the paperwork. Rawlings didn’t have to keep telling Kannenberg’s story once the deal was done. The fact that Gas Monkey did anyway is what turned a straightforward collection-buy video into the one Rawlings ranks above a barn full of Hemi cars and a seven-figure Wisconsin score.

It also says something about where this kind of content is heading. Gas Monkey Garage built its name on the flip — buy low, wrench hard, sell high, repeat. This video is still technically about that formula, but the ranking itself gives away what the crew actually values: not the biggest check written, but the biggest life attached to what got bought. A factory-lightweight Coronet and a 69-built ZL1 will always pull a crowd on their specs alone. A racer who spent two decades sideways on dirt and built an empire out of wrecked motorcycles is a harder story to tell — and, on this list, apparently the one worth telling most.

Watch the full video above and let us know your thoughts in the comments.