Member Spotlight: John Bennett

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The Cowboy Way with John Bennett

The beauty of the Checkered Flag 200 is that members come from all over the map, all walks of life, and all niches in the automotive world. John Bennett hails from Big Sky Country, but his horse isn’t the kind you’d see tied up in front of a saloon but the prancing, Italian variety. Born in Alaska and raised in Colorado, Wyoming, and Virginia, Bennett’s family eventually settled in Montana where he spent his formative years driving his father’s Fairlane under the state’s big sky. 

Once infected with the car bug, John attended university, moved to California, got a master’s degree, and attempted a normal life working for a Fortune 500 company – but couldn’t stay away from his true passion. He returned to Montana for a JD, and upon becoming a lawyer set out to blaze a new trail that would immerse him in the collector car world and create a cottage industry helping other car guys around the country in the process. 

Bennett’s Missoula, Montana, based law practice is a full-service shop, but their specialty is in helping businesses and collectors set up LLCs for the purpose of estate management. From single large ticket purchases to the management of entire vehicle collections, his team works with collectors with everything from taxes to vehicle registration – eliminating a huge headache for many collectors. As a result, he gets to spend most of his day talking to fellow car guys – not something most attorneys can claim. 

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When Bennett is not in his office he can be found behind the wheel participating in events with friends. He has been competing in both the Going to the Sun Rally and Ramshorn Rally for the past five years and encourages anyone with a passion for classic cars to join him on one of the events as a good way to take in the beauty of Montana.

While Bennett has an eclectic collection of cars including a classic F100, a 1958 Fiat 1200 Turisimo Veloce and a pair of Ferraris - a 1978 Ferrari 308 GTS and a 2008 Ferrari F430 Spider, he also still owns that same Ford Fairlane, purchased new in 1956 by his father. The car has since received a full restoration and spends time with both Bennett and his twin brother.

Asked about his favorite, Bennett says he loves spending time behind the wheel of his 1967 Fiat Dino Spider. While it only has 160 horsepower it is the intoxicating sound that grabs him when enjoying the open road with the top down. However, he still has the “Need for Speed” which is helped by his friends - one, in particular, lent him the keys to a Ferrari 599 Aperta - and he said it was hard to give the keys back.

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While Bennett doesn’t live in Los Angeles he believes strongly in The Petersen, which is why in 2016 he became a CF200 member after being invited to attend the Re-Opening of the museum. Bennett opted to become a lifetime member to show his appreciation towards the museum and all it does for car culture nationwide. He thinks that others should follow his lead because of the value the museum brings to fellow car lovers and it needs true car guys and girls to appreciate and support it.

He may not ride a horse or wear a big hat, but John Bennett believes in enjoying the open road, wind in his hair and sun at his back with a smile on his face – the cowboy way – and we are proud to have him as a lifetime member of the Checkered Flag. 

Written by Finish Line Staff