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It was 1999 when Cynthia Clapham’s boyfriend agreed to sell his 1972 Cadillac convertible to her for $5,000.
“He had bought the car, and I told him at the time if he ever decided to sell it, I wanted to buy it,” the Bloomington woman said.
Hugh Jessup drove the classic Cadillac quite a lot after buying it in the early 1990s, once driving the giant car to eastern Canada towing a boat.
Clapham had fallen in love with the Fleetwood Eldorado and was happy when Jessup decided to sell and buy a Mercedes convertible for himself.
She paid $2,500 up front and signed a note promising to pay the rest over the coming year.
Then, she said, Jessup ended their relationship. She drove off in the Cadillac.
“After he broke up with me, I really did kind of forget about paying him. Then when I remembered, I didn’t really care. We didn’t speak for the next 3 or 4 years.”
In 2005 he sent her a letter that included the promissory note she had signed when she bought the Cadillac. “He wrote that it didn’t look like I would be paying it,” she said, “and he forgave the loan.”
A decade later, the two got back together and became life partners.
“For a long time after we broke up, I remarked that the car was the best thing I got out of that relationship,” Clapham said. “But then I had to stop saying that.”
Clapham still had the Cadillac when they reunited, the red upholstery a bit worse for wear because she often had a 120-pound front seat passenger: a Rottweiler named Molly she would strap in with the seatbelt.
“She loved going for rides in the car. Her ears would just fly in the wind.”
Clapham said her father, the late Chuck Clapham, also enjoyed being driven around town in his daughter’s majestic car. He was 83 when he died in 2003 and is still with her when she’s out and about in the Caddy.
“I had some of my father’s ashes I had scattered and there was some residue left in the bottom of the container,” she said. “I left it in the car. ‘Hey, daddy. Let’s just go for a ride,’ I say to myself.”
Sure enough, there’s a white plastic bowl with a lid there on the back seat floorboard.
Clapham has had some work done on the car this past year. The wiring and hoses were replaced, and the drum brakes were adjusted to stop faster. She bought new tires with 4-inch-wide whitewalls; the old tires had been on the car since 1999.
Driving the Cadillac brings her joy. “I can be in a bad mood or unhappy and I get in that car and put the oldies in my cassette player,” she said.
“And that puts a smile on my face every time I drive the car.” Everywhere she goes, people ask if she wants to sell it. “The answer is, of course, no.”
The elegant car, original down to the paint, is a legacy that will be passed on to her daughter.
She scoffs when her 18-year-old grandson says the car is just too big. “I grew up driving Buick Electras. We always had big cars,” Clapham said. “I can parallel park this one. I don’t normally go anywhere where I have to, but if I did, I could.”
The car is nearly 19 feet long and weighs close to 5,000 pounds. Hers is one of just 7,975 Fleetwood Eldorado convertibles Cadillac made in 1972.
The cost off the showroom floor 52 years ago was $7,680, which is equivalent to $58,000 in 2024. It was a high-end luxury vehicle in its day.
Still is.
Clapham teases Jessup about that $2,500 long-ago debt, “and that he’s never going to see it."
Editor's note: This story was originally published in December 2024.
Have a story to tell about a car or truck? Contact My Favorite Ride reporter Laura Lane at llane@heraldt.com or 812-318-5967.
This article originally appeared on The Herald-Times: How a 1972 Cadillac Eldorado convertible became a rolling love story: Photos
Reporting by Laura Lane, The Herald-Times / The Herald-Times
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