Story and photos by Brian Earnest

General Motors assembled more than 142,000 of its glorious, glamorous and glitzy 1959 Cadillacs as the era of big fins reached its zenith.

Mike Siegal always held out hope that there was one out there somewhere that was meant to be his. The old car-loving Skokie, Ill., resident dreamed for years of owning one of the famous Caddies with the cartoonishly tall tailfins, but there came a point when he began to lose hope.

“It’s always been a dream car for me, and I waited a long time … And all the time I figured it was getting further away,” Siegal recalls. “You now how that is. You want a car, and you wait, and it just keeps getting more expensive. You want a ‘60s Corvette? Forget about it! Now they are all over $50,000. So that’s the way I figured it was going for me.”

Siegal finally got the kind of lead he was hoping for on a car — a 1959 Series 6237 two-door coupe — that sounded promising, but even that turned into an exercise in more patience. “A friend in my synagogue was telling me about this car for a year, and I kept saying ‘Get me the phone number!’ I waited a year before I could get the number and call the guy.”

Oddly, Siegal never actually wound up talking to the owner of the Cadillac. Instead, he dealt with the man’s son. It all worked out in the end, however, and he had finally stumbled on a car that fit both his tastes and his budget.

“I never met the guy who sold me the car. I never even talked to him,” Siegal laughed. “I only talked to his kid, and I bought this car without a title… The guy just lost it. He had a bunch of old cars and he was an older guy, and he just lost it. But I did my due diligence. I checked all the states around and made sure it wasn’t stolen or anything. I’ve been bringing the car to shows for 20 years and nobody has ever come up to me and said, ‘Hey, that’s my car, I want it back!’” [laughs].

Siegal did eventually get a title from Illinois for the beautiful red-and-white coupe, and he has enjoyed many miles of smooth sailing every since. At last check, the odometer had rolled past 117,000 miles with no end in sight. More than 2,000 of those miles have been tacked on during Siegal’s annual trips north the Iola Old Car Show in Iola, Wis. “It’s 225 miles each way — 450 miles round trip, and I’ve driven to Iola five times now,” he says proudly.

Siegal is a gregarious and outgoing sort, which is a good thing considering how much attention his Cadillac draws. He knows he will never be anonymous when he shows up anywhere in his bright red dream boat, and he’s meeting plenty of new friends because of it. “This is a car that everybody looks at. Little kids, old ladies — everybody looks at it. If you want attention, this is the car to have,” he says.

Certainly no other car better symbolized the fabulous, flamboyant 1950s better than the 1959 Cadillac. The “Bat-Wing” 1959 Chevrolets and “Forward Look” Chryslers were head-turners, too, but nothing could top the 1959 Cadillacs when it came to attracting eyeballs. The stunning new 1959 design featured huge vertical tailfins, twin bullet tail lamps, two distinctive rooflines and roof pillar configurations and new jewel-like grille patterns with matching rear beauty panels.

The former 62 line was officially called the 6200 series in 1959 and was actually comprised of three sub-series, all with similar wheelbases and lengths. The five base Series 62 models were identifiable by their straight body rub moldings, running from front wheel openings to back bumpers, with crest medallions below the tip of the spear. A one-deck jeweled rear grille insert was seen. Standard equipment included: power brakes; power steering; automatic transmission; dual backup lamps; windshield washers and two-speed wipers; full wheel discs; outside rearview mirror; vanity mirror; and oil filter. The Series 62 convertible also had power windows and a two-way power seat. Plain fender skirts covered the rear wheel openings and hardtop sedans were available in four-window (Model 6239) and six-window (Model 6229) configurations.

The Series 6237 two-door coupe was actually the least-expensive model in the entire Cadillac family for 1959, but its timeless hardtop design has kept it among the most popular models with car buffs and collectors. The pillarless coupes carried a base price of $4,892 and weighed in at 4,690 lbs. With 21,947 assemblies, they were second in popularity among all ’59 Cadillacs behind only the Series 62 Model 6229 four-door hardtop sedan, commonly referred to as a six-window sedan for its fixed vent window on each rear door. The coupes and six-window sedans both had rooflines that gracefully arched down to the rear deck. Meanwhile, the four-window “flat-top” Model 6239 sedans had rear glass that dramatically curved between the vertical C pillars.

Under the hood of the Series 62 was a standard 390-cid V-8 rated at 325 hp, which was 15 ponies and 25 cubes more than the previous year’s 310-hp/365-cid V-8. Hydra-Matic shifting was standard, as was dual exhaust. Series 62s measured 225 inches from tip to tip and rolled on 130-inch-wheelbase chassis.

Siegal doesn’t have a lot of details about his car’s history before his 20-plus years of ownership, but he knows the coupe was restored at some point. “It was a black car and it had a black-and-gray interior,” he said. “So somebody spent an awful lot of money on this car. The VIN says it was black. When I had it repainted, I could have had it painted black, but it would have been a lot more trouble. Everything was red on the car by then, and I like red, so I kept it red.

“It’s got power windows, power seats… It’s got aftermarket air conditioning, AM radio, power steering, power brakes, automatic [transmission]. It’s got the Autronic-Eye, which is supposed to turn off the high beams, but it doesn’t work.”

Siegal’s car shows plenty of patina inside, which only adds to its charm. The red-and-white dash and steering wheel don’t completely hide their age. The vinyl seat upholstery had been re-done in red and white by the time Siegal bought the Cadillac, but he’s had the driver’s seat reupholstered once since then. The red paint outside still looks great, but Siegal says the chrome is largely original and could use some work. “There are a couple of rough spots, but once you start with the chrome, there is no end to it, and chrome is a fortune!” he laughs. “I have a ’57 Buick convertible also, and another guy that has one told me he just spent $15,000 to re-chrome the bumpers. I don’t want to spend that kind of money [laughs].

“It drives pretty nice. It’s not big on acceleration. But it drives pretty smooth. I think the engine and trans have been rebuilt on this thing. Like I said, somebody spent a lot of money on this car at some point.”

Siegal has always loved the car, but he admits that he actually got talked into selling it once a few years back. The incident still has him shaking his head. “It was probably about 6 or 7 years ago somebody came to me and wanted to buy it. They kept after me and kept after me. Then I finally told the guy I would sell it to him, and he said, ‘No, I’m not interested.’ I was so [mad], because I didn’t want to sell it in the first place!”

Considering Siegal waited such a long time to find it, and has found so much enjoyment behind the wheel for more than two decades, it’s almost a guarantee the big coupe won’t be changing owners anytime soon.

“I was very happy to get this car, plus to get a red one! You can’t beat that,” he says. “I just want to be able to go to a [car] show. I want to have a nice car and be comfortable and have a good time. I like this one just the way it is.

“To me, it’s a special car.”

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