JULY 2026: 1950 CHRYSLER WINDSOR DELUXE—IT’S A PIECE OF HIS BIOGRAPHY

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The first car is the biggest deal in a kid’s life but most of them are gone within a few years– and the only thing left is the memories.

That’s how it plays out in the real world because the first car is usually a beater with no upside and lot of miles.

Most guys leave the first car in the past, but this 1950 Chrysler Windsor Deluxe is a completely different story.

Jerry Sutherland

Mike Maeder fell into the deal on this old Chrysler back in 1968 when his uncle found it in a barn “under bales of hay”. The car had been there for years, and Mike bought it for the massive sum of sixty dollars. 1968 was part of an era when unloved early 50s cars had little to no value so while the number seems low, that’s what the market was for these old warriors.

This is a flathead six car with the fluid-drive semi-automatic, so Mike wasn’t getting to the party fast, but he was getting there in style. He didn’t get into details, but Mike did mention, “The stories it could tell”.    

Mike put the old Chrysler through its paces back in ’68. He discovered the front bumper was a great seat for “beer drinking and watching the stars” with his buddies. He tore a right rear fender off the car when he hit a pylon, and he hit a Triumph TR4 in an alley.

The Triumph took a beating on that encounter because his Chrysler ended up with a scratch on the bumper and the TR4 was nearly written off.

That might be the end of the story for the Chrysler because life moved on for Mike. He was part of the 101st Airborne in Vietnam so he served his country and the Chrysler became a part of his memories.

But it never went away because Mike never forgot his first car. He said he “came into a little money” when he started his own business and he began to track down his old car to see if it was even around.

Mike explained how it was easier to track down a car through its registration back then, so he learned it was still on file and who owned it. Mike called the owner and found out the car was not only still around—it was also just recently restored, and it was for sale.

That was all Mike needed to know, because he bought the car and didn’t even negotiate on the 6000-dollar asking price. He knew the odds were against the Chrysler after it left his hands, so he wasn’t going to lose it on a number he didn’t like.

The Chrysler survived the years well, because it still looks mint. The previous owner did all the right things to freshen it up and now Mike is back behind the wheel of his first car.

This story proves why everyone should try to track down their first car—you might strike gold like Mike did.                  

Jerry Sutherland

By: Jerry Sutherland

Jerry Sutherland is a veteran automotive writer with a primary focus on the collector car hobby. His work has been published in many outlets and publications, including the National Post, Calgary Herald, Edmonton Journal, Ottawa Citizen, Montreal Gazette, Saskatoon StarPhoenix, Regina Leader-Post,  Vancouver Sun and The Truth About Cars. He is also a regular contributor to Auto Roundup Publications.

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