The 1955–58 Cadillac Eldorado brought a rise in power … and tailfin size

When it comes to classic Cadillacs, modern-day admirers tend to gravitate toward the big-finned 1959 models.

In fact, one of the star cars at Barrett-Jackson’s upcoming May 8–17 online auction is a 1959 Cadillac Eldorado Seville Custom Coupe that once belonged to Hank Williams, Jr. The country music superstar released Red, White & Pink Slip Blues in 2009 but likely didn’t have to hand over the keys to his Caddy to cover the rent. The Dakota Red Eldorado—among the first cars scheduled to cross the block—carries an average #1 (Concours) value of $92,900 and a #2 (Excellent) value of $70,500.

With all due respect to the ’59 models, if you want Cadillac class but prefer slightly more subdued styling, the 1955–58 Eldorado may provide the happy medium for which that you’re searching. By happy, however, we don’t mean cheap, even though Hagerty valuation editor Andrew Newton says the cars have experienced “generally declining interest over the past couple of years and are now worth less than they were 10 years ago.”

Regardless, “They’re very expensive to restore—given all the sheetmetal, chrome, and trim—so the very best examples hold their own.”

Although Cadillac’s 1955 lineup may have resembled its 1953 and ’54 cars, the Eldorado’s 331-cubic-inch V-8 received more power (a boost to 270 horses), and the car gained longer, taller tailfins not shared with any other Cadillac. Sales increased to 3950—up from 2150 in ’54—and the price increased slightly to $6286 (more than $62,000 today).

In 1956, a new Eldorado Seville two-door hardtop coupe joined the ranks and nearly outsold the convertible 2 to 1. The cars received a special 305-hp, 265-cu-in V-8, while other Cadillacs had to make do with 285 horses.

An entirely new redesign arrived in 1957 and the Eldorado was given a lower stance and larger tailfins while maintaining its horsepower advantage over other Cadillacs. Added to the lineup was a hand-built four-door hardtop variant that cost an eye-popping $13,074—$120K today—nearly double the price of the Eldorado Biarritz convertible ($7286, or $67K in today’s dollars).

Only 400 four-door Brougham sedans were built, and they featured rear-hinged rear doors and Cadillac’s first use of quad headlamps. Those features were supplemented by “memory” power seats, a stainless-steel roof, and standard (but often problematic) air suspension. Most of those systems have since been replaced with conventional springs.

“All of these came with a vanity set with stuff like drink tumblers, cigarette case, tissue holder, and a cosmetic case with comb, mirror, lipstick, and coin holder,” Newton says. “These things are nearly impossible to find, so a Brougham without them is valued about $15,000 less.”

A two-door hardtop was also available and, oddly enough, “These are the cheapest overall, with a median #2 value of $53,200,” Newton says. “But they’re also the only Eldorados from this period that have gone up—about 7 percent in the last three years.”

Despite the popularity of the two-door hardtops—and the rarity of Broughams—Eldorado Biarritz convertibles are the highest-valued Cadillacs from the period. The most expensive is the 1957 model, which is worth $202,000 in #1 condition and $130,000 in #2. (The least expensive—a 1956 Eldorado Seville—is worth $68,100 in #1 and $45,600 in #2.)

Eldorados received minor changes for 1958, although 305 top-of-the-line, Pininfarina-bodied four-door Broughams were built and sold, again starting at $13,074. The Seville two-door hardtop and Eldorado Biarritz two-door convertible each sold for $7500. All cars but the Biarritz featured the new front styling with quad headlamps that was unveiled a year earlier.

Not surprisingly, interest in 1955–58 Cadillac Eldorados is highest among older enthusiasts. Half of all insurance quotes for these cars come from baby boomers, while 27 percent come from Gen-Xers, 17 percent from pre-boomers, and 5 percent from millennials.

“Given the age, size, and especially the expense of these cars—not to mention they’re not particularly fun to drive—it’s not a surprise that young buyers haven’t taken a liking to them,” Newton says. “They generally prefer sportier cars.”

Among the recent eye-opening prices paid for 1955–58 Eldorados was $275,000 for a 1956 Biarritz at Barrett-Jackson’s 2019 Scottsdale Auction and $264,000 for a 1958 Biarritz at Mecum’s 2018 Indianapolis Auction. Five years ago, RM Sotheby’s sold a 1958 Biarritz “Raindrop” prototype for $324,500.

Of course, if you’re looking for the biggest, baddest Cadillac tailfins ever, there’s always the ’59.