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Hagerty Makes a RADical Acquisition

Purchase of RADwood car show is a win for the insurance firm, car lovers

By Leo Shvedsky
March 15 2022
The Ferrari that met Santa. ( 

Lately Hagerty has been on a shopping spree worthy of Julia Roberts’ character from “Pretty Woman.” The insurance company has been diversifying for years, and recently it has been wading into the car enthusiast world. Its recent purchase of RADwood has solidified its standing in the car collecting world even further.  

RADwood has taken the ’80s and ’90s car collector’s world by storm over the last five years. It began in 2017 when four friends — ’80s/’90s car enthusiasts all — decided to start a car show with their collections in a park in San Francisco. Since then, the event has grown to ’80s shoulder pad proportions, with a show basically every month all around the world.  

Nothing says the ’90s like a Porsche line-up! ( 

With stunts like driving a Ferrari 308 across the Arctic for 1,000 miles or the Ford F-250 which was “overrestored” by its owner to be the ToolTime truck from ’90s sitcom (and Tim Allen launchpad) “Home Improvement,” both featured at RADwood shows, we are ALL IN.  

Infamous in the 1990’s.... the Vector V8. (Hagerty Instagram)

Hagerty’s attraction seems obvious: The goal of CEO McKeel Hagerty — the second-generation company steward — to “save driving” coupled with RADwood’s goal of sharing amazing (and sometimes not-so-amazing) cars of the last decades of the 20th century go together like Seattle and rock ’n’ roll.  

Hagerty started in 1984 as a marine insurance firm under McKeel Hagerty’s father, Frank. The company made a name for itself in that market, but in the late ’90s, when McKeel and his sister, Kim, started working at the company, they made moves into the auto collector’s world by offering solid coverage plans for collectors who buy classics.  

It’s not the ’80s without a classic BMW. (RADwood Instagram) 

Since then, Hagerty has been the name for insurance in the collectors’ world. It even has king collector himself Jay Leno writing a whole column for them. But for Hagerty, it is not just about the bottom line. Sure, it keeps buying car shows and auctions like the Amelia Island Concours, but it doesn’t seem to come with the kind of corporate takeover nonsense these things sometimes have: cutting or downsizing to increase returns, or changing the brand to fit some overarching strategy to take over the world.  

That’s what makes the RADwood acquisition so cool. Hagerty is keeping the founders on for continuity because it doesn’t want to mess with what is totally tubular about the show.  

The way to a real 80’s kids heart. (Radwood Instagram) 

Furthermore, Hagerty keeps its own fleet classics that are all bought and restored at company expense specifically for the purpose of taking them to shows for enthusiasts to drive for free.  

It’s this dedication to the community that we think make this acquisition not just another in a long line of takeovers and mergers that lead to dystopian end. This move seems to be steeped in the enthusiast tradition and fervor for classics. And should some folks end up with an insurance policy from Hagerty, maybe everyone is the better for it. 

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