There’s usually no drama associated with cars making their way into Jay Leno’s Garage – he either owns them or the people who do keep them running right. Things were a little different with this 1966 Mercedes-Benz 230 “Fintail.”

Its current owner, Randy Carlson, founder of the automotive exploration and recovery site Carchaeology, has performed some crucial maintenance and replaced some key parts since he bought the sedan. But that’s because it used to be in much rougher shape.

While appraising a collection of largely German cars in Alabama, he discovered this green 230. After buying it from the aging owner and being told it ran well, Carlson had the wild idea to just wing it and drive the car 2,000 miles back to his place in California. What he had been told was technically true: the car was functional overall, but many of its parts didn’t work. Its heater was shot, just like its speedometer, odometer, and horn. The clutch and the four-speed column shifter didn’t act right. In addition, there was a brake vacuum leak. At one point in Carlson’s long journey home, the 2.3-liter inline-six started running poorly, necessitating an impromptu carburetor cleaning.

Since getting the car back to his place in California, Carlson has tended to some of his Fintail’s issues. He installed a new clutch slave cylinder, adjusted the valves, and had the brake booster rebuilt. The heater, horn, and instrument issues will have to be resolved some other time.

Although Carlson’s decision to drive a strange old car for three days across the country may not have been the most level-headed, he knew how to fix things on the go, which created a bond between him and his W111.

Did the Fintail survive Leno’s test drive? Click the play button below to find out.