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Car of the Week: 1956 Cadillac Sixty Special

Danny Plotkin’s aching back wasn’t funny at the time, but he can laugh about it now. He knows that if it wasn’t for some unpleasant lumbar pain, he never would have wound up with his favorite ride: a 1956 Cadillac Fleetwood Sixty Special that knocks ’em dead wherever he takes it.
Car of the Week 2020

By Brian Earnest

Danny Plotkin’s aching back wasn’t funny at the time, but he can laugh about it now. He knows that if it wasn’t for some unpleasant lumbar pain, he never would have wound up with his favorite ride: a 1956 Cadillac Fleetwood Sixty Special that knocks ’em dead wherever he takes it.

Buying an old, jumbo-sized Cadillac was the last thing on Plotkin’s mind when he was hobbling around the grounds at the AACA Hershey fall extravaganza 3-1/2 years ago. All he could think about was getting some relief from his throbbing back.

“I could hardly walk, so I decided to go out and sit by the cars and wait for my friends so we could go home,” recalled Plotkin, a resident of Longmeadow, Pa. “So I went out there to sit on the curb and lament my bad back, and I look across the way and see a kind of faded ’56 Fleetwood for sale. I said to myself, ‘That Fleetwood looks like a good place to sit. I’ll go sit in that. It’s a comfortable car and I’ll pretend I’m interested in buying it.’ So I waddled over and sat behind the wheel and the old guy who owned it came over and tried to sell me the car — he was dangling the keys and telling me all about the car.”

Plotkin wasn’t overly impressed at first, but the longer he sat in the Fleetwood’s plush upholstery and the more he heard the owner gush about how nice the car was, the more interested he became. When his buddies showed up, a predictable outcome followed. “You know how it is when a pack of guys get together and one of them is interested in car!” he laughed.


“The guy was real honest with me. It was an 80,000-mile car. The chrome wasn’t very good, but it had no rust. It had some painting done on one panel, unfortunately, but it was a good, honest car and I felt I could live with the car the way it was … So I bought the car and we jumped in and drove it 300 miles home.”

The drive home didn’t initially go well, however. The big sedan conked out on the highway several times before the men finally got it home. They thought they had a case of vapor lock on their hands, but “that was a red herring. That was not the problem,” Plotkin said. “There was piece of epoxy floating around in the fuel line, and every once in a while it would get stuck.”

The car also lost fourth gear on the way home, so one of the first orders of business was fixing the transmission. The carburetor was overhauled, the Cadillac received a new fuel tank, a little TLC and “it ran like a champ and it was a beautiful car to drive around,” Plotkin said.

The Fleetwood wound up running and driving better than it looked, which had Plotkin pondering what he wanted to do with it. If it wasn’t a big luxury cruiser, he wouldn’t have minded it looking a little tired. “The car ran so great, the [crummy] paint and chrome made me feel bad,” he said. This is a Fleetwood, you know? Finally, my wife [Mollie] said, ‘Why don’t you fix that?’ So I got a purchase order from my wife and we took it in for a restoration in August of 2011 and finished it in July of 2012 … It was more a cosmetic restoration. We didn’t do anything mechanically, but we repainted the body and fixed all that chrome.


“Now it looks exactly like it runs and it’s otherwise an original car … It drives the way it did when it was built. It was a lot of fun [to restore] and I’m glad I did it. It’s not as valuable as the convertibles, or an Eldorado … but the Fleetwood was still the most expensive [Cadillac] you could buy back then beyond the Eldorado.”

The Cadillac still wears its Dawn Gray body color, but the previous owner changed the roof color from Canyon Gray to Starlight Silver Metallic. It is a color combination that certainly works well together and perhaps makes the Cadillac a little less serious and intimidating.

“I thought the old roof color looked like toothpaste. I like this color a lot better for the roof.” Plotkin said. “It’s not a black Cadillac, so it’s a little different. A lot of these Fleetwoods were black or dark blue and they were used in funerals or to cart around heads of state.

“It’s a striking color combination. It’s very, very pretty … The Starlight Silver Metallic was an Eldorado color that you could have on any Cadillac for extra charge.”

The 1956 model year was the end of an era, of sorts, for Cadillac as the marque’s trademark tail lamp-capped tailfins made one final appearance. The Fleetwood Sixty Specials were the company’s mini-limousines, squashing the scales at 4,992 lbs. and carrying a luxury price tag of $6,019 without any add-ons. The 1956 Fleetwoods measured 225.9 inches between the bumper tips and rode on 133-inch wheelbases.


Cadillac churned out 17,000 of the big six-passenger sedans in 1956, which carried new egg-crate type grilles and subtly different trim arrangements than the previous versions. A thin chrome strip ran along the top of the rear fenders with fat chrome spears pointed forward on the sides of the rear flanks. Prominent oval exhaust ports exited out of the upper corners of the rear bumper.

Under the massive hood was an updated and enlarged 365-cid V-8 rated at 285 hp hooked to a Hydra-Matic transmission. Plotkin knew about the ’56 transmission and its reputation for having reliability issues long before he bought his Cadillac, so he wasn’t surprised when it needed work. “I’ve always had a penchant for the ’54, ’55 and ’56 Cadillacs. Those three years was that series body, and a friend of mine used to sell those cars when they were used back in the ’60s and he warned me never to buy a ’56. He told me to always buy a (’54 or ’55). They were just a better car … And it’s a known fact in the hobby that the 1956 Hydra-Matic was a very problematic transmission. There were tons of service bulletins on them. They had it all sorted out by ’58.

“But I bought a ’56 anyway!”


Plotkin doesn’t know the entire life story of his Fleetwood, but he does know it was sold new in Minnesota and the way it was ordered from the factory makes it unique.

“This was [a]... special-order car that year. They called them ‘special request’ cars in which the interior upholstery was a little different. Standard equipment in this car would have been cloth seats with a leather border around the edges. This car was ordered by special request to have broadcloth instead of leather … The car came from Minnesota and it’s likely whoever bought it thought that leather was too cold…and it also doesn’t have air conditioning, which is unusual for this car. Most of them had air.”

“I can’t find any other history beyond the guy I bought it from got it from a classic car dealer in Nyack, N.Y. … It’s just not even close to being a worn-out, used-up car. It had very gentle use all its life. To be that old and be in that condition, and have only 80,000 miles, obviously it wasn’t used very much.”

These days, the car gets exercised regularly and will be a fixture at car shows in the coming years, although Plotkin has a fleet of other big cars that also have to get driven. The Fleetwood shares garage space with a 1960 Buick Electra sedan, 1962 Pontiac, 1961 Plymouth Savoy two-door sedan, 1963 Ford Galaxie XL, 1963 Chevrolet Impala convertible, 1965 Corvette and 1968 Chrysler New Yorker. “I’ve got seven iron and one plastic,” he jokes. “It’s a disease.”


Plotkin says the Cadillac is his favorite to drive, and the most fun to pilot on back-road cruises, in part because it doesn’t feel as modern as many of his 1960s cruisers. “The ’60 Electra rides like a magic carpet. The Cadillac is not like that,” he says. “These cars are a lot different from the ’60s cars. They were mid-’50s Cadillacs designed in ’50-’51, and they are still technologically an older car, but still a good road car. They are kind of like a modern pickup — smooth, but a little bouncy… And everything they do, they do effortlessly. It’s a 5,000-lbs. car and it only makes 285 hp, but it never runs out of power. It does everything without complaining.”

The Cadillac is clearly in line for many more happy miles with the Plotkins in the front seat. With any luck, the odometer might turn over in a few years. Danny certainly isn’t worried about rolling up some more miles. He figures the Fleetwood is all rested up.

“Oh, I’m not worried at all about using it,” he said. “I plan on using it and enjoying it. Old cars like this, if you take care of them and use them, they stay nice for a long, long time.”



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