A Chrysler Imperial That’s an Emblem of the Roaring ’20s

Joe Wortley, 75, a semi-retired entrepreneur and C.P.A. from Boca Raton, Fla., on his 1929 Jack Dempsey Chrysler Imperial Roadster, as told to A.J. Baime.

I am a collector of things that may seem odd to some, but they have meaning to me. I own an Apollo 13 mock-up that was used in the Tom Hanks movie “Apollo 13,” a 19th-century pipe organ that is bigger than a car and a nearly full-scale re-creation of Charles Lindbergh’s Spirit of St. Louis airplane. My most noteworthy car is a Chrysler that once belonged to Jack Dempsey, the world heavyweight boxing champion for much of the 1920s.

I bought the car in 2001 from the late Tom Lester, founder of the Lester Tire Co. who was also a master car restorer. After he restored the vehicle in the 1970s, it won a first-place award at a Classic Car Club of America national competition.

Drive Back in Time in a 1929 Chrysler Imperial

Joe Wortley, of Boca Raton, Fla., says he is the ‘custodian’ of a sparkling Chrysler Imperial once owned by former heavyweight boxing champion Jack Dempsey

‘It is a fine driving car,’ Mr. Wortley says. ‘It rides beautifully at 60 mph.’

Joe Wortley with his 1929 Chrysler Imperial, which once belonged to Jack Dempsey, heavyweight boxing champion for much of the 1920s.

The Imperial was Chrysler’s high-end offering, introduced in the 1920s to compete with Cadillac and Lincoln. According to a Wall Street Journal article from Dec. 6, 1928, the price ranged from $2,675 to $3,475—a lot of money at the time.

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Turning those front wheels requires some muscle, says Mr. Wortley. This car has no power steering.<br>

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The hood ornament exemplifies Roaring ’20s luxury. When this Chrysler was built, the company was also building the now-famous Chrysler Building on Lexington Avenue—for a time, the tallest building in the world.<br>

The whitewall tires are from the Lester Tire Co., which was founded by the car’s previous owner, the late Tom Lester.

Another view of the Jack Dempsey Chrysler. Mr. Wortley says when he was a child, around 1950, he met Mr. Dempsey at Jack Dempsey’s, a famous New York restaurant. ‘He was larger than life,’ Mr. Wortley says.

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The interior is original, according to Mr. Wortley, who calls himself a ‘custodian’ of this car. ‘I want to keep it in great shape,’ he says.<br>

A close-up of the Chrysler Imperial badge. Chrysler continued to sell cars called Imperial into the 1990s.

The rear of the car, with its sparkling chrome.

The car has a rumble seat in the back.<br>

A door opens to allow easy access to the rumble seat.

Joe Wortley with his 1929 Chrysler Imperial, which once belonged to Jack Dempsey, heavyweight boxing champion for much of the 1920s.

Andriana Mereuta for The Wall Street Journal

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Mr. Lester told me that the car had belonged to Mr. Dempsey. A friend of mine who worked at Chrysler confirmed this fact and sent me a photo he said showed the boxer picking up the car at the Chrysler factory. A quick Google search turns up this same photo. (The car was all black at the time.)

People today don’t realize how revered the sports stars of the 1920s were. Babe Ruth, the tennis player Bill Tilden, Mr. Dempsey—these people were unbelievably famous.

The vehicle is interesting for other reasons as well. It was built at a time when Chrysler was still run by its founder—Walter Chrysler—and it is a 1929 model, which means it is emblematic of Roaring 1920s extravagance, right before the stock market crashed. The Imperial was Chrysler’s high-end vehicle, the company’s answer to Cadillac and Lincoln.

As was custom with some high-end cars at the time, the car company would build the mechanical vehicle and a “coach builder” would construct the body, which meant that many of these car bodies were hand-built and unique. My car’s body was made by a company called Locke, which also made bodies for Rolls-Royce.

The car has its original six-cylinder engine, just over 5.0-liters. I like to drive it around town. It can be hard to steer (there is no power steering) and parking a car like this in Boca Raton can be quite a project. But the car always draws a crowd, just like Jack Dempsey did back in the day.

‘The car always draws a crowd,’ Mr. Wortley says, ‘just like Jack Dempsey did back in the day.’ Photo: Andriana Mereuta for The Wall Street Journal