Big Fin Therapy: How Buying a 1959 Cadillac Changed My Life

Have you ever tried pushing an ancient behemoth of a car uphill on an interstate off-ramp? By yourself? At the peak of summer? In a three-piece suit?

If so, the thought that urgently ricochets around inside your head is, “This is not the sort of thing smart people do.”

But that was me not so long ago, struggling against -- and losing to -- inertia on Indianapolis’ south side, puffing red-faced as my car inexorably began to roll back down the hill toward 70 m.p.h. traffic. What I lacked in strength I compensated for in coward’s wisdom, jumping back into the driver’s seat to mash the brakes before I’d gone more than a few feet.

Before you’re tempted to declare me a weakling, I should mention the car in question is a 1959 Cadillac sedan -- almost 20 feet and 5,000 pounds of heyday Detroit manufacturing, back when steel was steel and bumpers were the sole safety feature.

I wish I could say this was the first time the Caddy broke down on me, but in truth it was the sixth or seventh. I purchased the car in late 2015 from a local dealer who specializes in antique autos, and he’d bought it from an old drunk who warned the dealer to show up early to finalize the transaction. “I start drinking at 10 o’clock,” the owner growled.

Old cars are much like old men: slow to wake from slumber, and stubborn to stop once they’re going.

The previous owner had been taking care of the car about as well as he took care of himself. It had mostly sat unrunning the past few years, a patina of rust starting to peek out here and there -- and in a few places, straight through -- the vast expanse of black metal, the chrome growing pitted and dull.

Mechanically, it ran under its own power but, in the immortal words of shadetree mechanics everywhere, the Caddy “needed a little love.”

Stuck transmission governor. The first, but hardly last, tow.

More than two years and thousands of dollars later, I still haven’t found the delta of the river of affection the car requires.

And that’s before taking it to the body shop for patching and paint… a process that can empty bank accounts faster than a meth addiction. Since I bought it, I’ve actually had the car in my possession maybe 10 or 11 weeks total.

So why me? Why this troublesome jalopy from a bygone age? Why all this frustration and unrewarded devotion? And why I wouldn’t trade it all for a line of Lamborghinis?

To answer that, you need to learn a little more about the car, and the guy (occasionally) driving it.

Instant icon

You may think you haven’t a clue about classic cars, but actually, everybody knows the 1959 Cadillac. It’s quite possibly the most iconic vehicle design ever, instantly recognizable by its low, sleek body, mountain’s worth of chromite ore on the front and a rear end with the multitudinous points of a dragon’s nape.

1959 Cadillac advertisement.

The single most famous feature, of course, is the towering fins, which rise up over the back of the car like the bony protrusions of a prehistoric predator. It was, quite literally, the apex of a decade of accumulating excess in car design, with American factories cranking out increasingly ostentatious metal beasts.

The fins got so big that, accordingly to lore, clumsy people were actually impaled upon them. The provenance of those tales is suspect, but nonetheless by the close of the 1950s the government stepped in, and for 1960 the otherwise largely unchanged Cadillacs featured much more circumspect fins -- sad little bips, like a toddler mimicking his dad flexing his biceps.

I’ve adored the ’59 Caddies since I was a kid. It’s hard to describe exactly why. Certainly, they are beautiful cars, but there are prettier. It has a massive 390 cubic inch engine; but these are land yachts, not racers, and no hot-rodder ever feared lining up next to one at the stoplight.

And there’s the off-putting martial aspect to its detailing, from the bullet taillights to the fender “gunsight” chrome edging to the front and rear grille pattern that look like rows of polished slugs. It’s practically a rolling NRA poster.

For me, there’s just something indescribably delicious about the yin-yang contrasts of the 1959 Cadillac. It has this odd, intriguing mix of modernity and antiquity, subtlety and braggadocio, gaudiness and grace.

Let me put it this way: the ’59 Caddy may not be the biggest, fastest or loveliest thing ever to roll off an assembly line. But it is the most American car ever made.

Man and machines

It goes without saying, the man is less interesting than the ride. But our stories roll together.

Middle-aged, middle-class dad who grew up in the suburbs and ended up back there, by choice. Loves movies, meat and NBA basketball. Started out in newspapers, rode that till the ride ended for many of us, wandered into marketing a few years ago, still pursues his passions on the side.

A lady, better than I deserve; two towheads little boys who make my heart throb a little every time I look at them. A dog, a decent house in a good neighborhood. Nobody’s idea of rich, but stable.

I’ve always been an old car nut. Before 1974, when the oil crunch and safety mavens ushered in the new era of fuel efficiency and crash ratings, American cars were distinctive, original, unabashedly stylish. It was easy to distinguish the 1966 model from the ’68. Folks traded in every three years, excited about the newest designs. Even low-end stuff looked good.

Today’s vehicles are much more functional, and utterly forgettable. Good luck telling a Camry from a Sonata from an Altima. Many otherwise sane people consciously choose gray as their car’s color. Heaven help us.

My first love was the 1969 Mustang fastback. By the time I became old enough to appreciate cars, they were already pretty old. I boasted to my dad I would buy one when I grew up. He laughed, dismissed it as a waste of money.

Dad's dream car remained a dream.

Later, he confessed his eternal regret at not getting a white Ford Thunderbird in 1956, the year they hung the spare tire on the back of the car. He thought that was cool, and was about to muster out of the Air Force with money to spend.

Learning my father’s lesson, in my 20s I bought a Mustang, dirt cheap and well-rotted. Had most of the exterior sheet metal replaced, did much of the interior myself. Paid for all of it with a cash advance, moving the balance from credit card to credit card until it was finally flush. Crazy.

I loved that car, and drove it all around. Still do.

Now comes the sad and weepy part of this tale. Like a lot of people since the Great Recession, I lost a lot of things. My career. A big chunk of my savings. People I loved. My youthful illusion of invincibility.

Life begins, life ends.

Five years ago, my dad passed after a long battle with cancer. Wasn’t much more than a bag of sticks at the end. But he was 82, and he was ready. Said so himself. Maybe they have white Thunderbirds in the beyond, with tires on the back.

Two years later, my oldest sister had her own bout with cancer, was undergoing chemotherapy and seemed to be doing well. One day she went into torpor, didn’t want to get off the couch. Took her to the hospital and the doctors thought she was depressed. Turned out the tumors had metastasized into her brain. Caused an ischemic stroke -- she was gone within hours, aged 47.

Six months after that, I sat in a very cold room as a doctor explained the type of brain tumor I had -- prognosis, treatment options and associated risks, long-term effects and outcomes.

Loss, then gain

OK, I’m guessing that right about now you’re thinking, “I started reading a story about cool cars and somehow wandered into Dostoevsky.” So I’ll pull this tragedy out of its tailspin now and assure you that I am not dying. At least, not any faster than you.

I don’t hear so well anymore, and I get dizzy and tired sometimes. But that’s about as far as it goes. They say that for brain tumors, I have the “good” kind. (Which is a ludicrous thing to say.)

What I did unexpectedly wind up with after this long march of despair was: dough.

Rachel passed at age 47.

My sister never married and made decent money, and had life insurance. It took a while to sort out because she left no will, but after probate my mother inherited a not inconsiderable amount of money, some of which she shared with me and my other sister.

My wife and I used a large chunk of the inheritance to shore up the boys’ college funds and take care of some household fixes. We also agreed to let me separate a portion of it for myself, in keeping with family tradition.

I considered opening an IRA, but I already have a couple of retirement accounts and they’re doing OK, plus I didn’t want the hassle of managing another. And it wasn’t the kind of money you hand to an investment broker; any returns would be so small they’d be eaten up by fees.

So, I sat on it. A year passed.

It’s not exactly clear when the notion of buying another classic car transmogrified from daytime fantasy into an actionable plan. Certainly, I was noodling around with looking up current prices of classic cars. I have a handful of favorites I’ve dreamed of owning: a 1963 Corvette split-window hardtop, maybe a ’65 GTO. Or the real prize, a ’59 Caddy. It’s standard daydreaming M.O. -- you see what stuff is going for and muse about winning the Powerball.

Because they’re iconic, 1959 Cadillacs are highly collectible and thus more valuable than a ’60 or a ’58. A nicely preserved or restored one was out of my reach. But maybe I could do like I did with my Mustang, buy cheap and fix it up over time.

Things quickly crystallized when I stumbled across the dealer, who specializes in old Cadillacs and Mercedes. I swung by his shop, a nondescript place near Downtown Indy, and found a treasure trove. Funny thing: despite always loving the ’59 Cadillacs, I think I’d only ever seen one in person before. The guy had seven of them on hand.

Pretty much on the spot, I resolved to buy the car. To paraphrase author John Green, I tend to make big decisions the way people fall asleep: slowly, then all at once. I’ll think about something for six months or a year, then a switch gets flipped. Only two logistical concerns had to be addressed before signing on the dotted line: my wife and my garage.

The latter was simpler; I needed to measure if my standard garage would house such a monster. The answer came quickly: juuuuuuuust barely. The whole thing came as a surprise to my spouse, whom I’d spoken to briefly about the idea not long before in purely hypothetical terms. She took it pretty well, letting me know it would be wise if I could take steps in the next few months to reassure her I was sane.

That is why

The first few weeks after the purchase were pure heaven. The reasons I first had for buying the Caddy were pretty obvious to any casual observer: I’d suffered a lot of loss, and needed something to fill that hole. Some people take up a new hobby, or pick up and move somewhere new. Others acquire strays: dogs, cats, spouses. I got a big-ass old car.

Also, since losing my journalism gig I’ve been playing things pretty safe. No big purchases other than replacing stuff that breaks. Very modest vacations. No life-altering risks.

Call it mid-life crisis if you want, but I needed to do the not-smart thing for once. The illogic of the move was its very appeal.

I actually stated writing this article right after the purchase, when the temporary high still had me buoyed on a cloud of optimism. Like all things it faded with time, as the timeline for the car’s refurbishment stretched from weeks to months to years.

It’s pretty much a routine at this point: the Caddy has moved from shop to shop, coming home for a week or two at time in between the next round of repairs. Then it’ll go to the next shop, usually for two, three, four months at a time.

So... many... electrical issues.

It largely spent the winter of 2015-16 under a blanket of snow in the Indianapolis neighborhood of SoBro. Last spring, I ached to drive it during the crisp, beautiful days -- but we were parted the whole season.

Fixing an almost-60-year-old car is not like taking your Honda to the corner shop for a brake job. Lots of parts you just can’t find, or they’re prohibitively expensive. Finding mechanics with the expertise to work on vintage vehicles gets a bit harder every year.

At first, I was frustrated as hell at the delays. Two months to have the instrument cluster rebuilt??? What do you mean that wasn’t the right part?!?

The worst thing is to have your vehicle labeled a “project car,” because that becomes code for “the last thing that gets worked on.” The boys at the electrical shop called me up after four months to say, as nicely as possible, that they were tired of looking at the thing and would I please come get it.

But as time has gone on, I’ve gradually learned to accrue more patience for the process. Oddly, the emotional bond I have with the Caddy has grown the longer we’re apart. Because we’re a pair: aging, a bit battered, often not given the respect we’re due… but still running.

Owning the Cadillac has been a wagon train of frustrations, yet somehow, I’ve learned to not only embrace but on some level relish those hindrances. Because unlike people, cars can always be fixed. No mechanical problem is unsurmountable if you’re willing to invest the time and resources to address it.

Each setback is a learning experience. Every time the Caddy has broken down on me, I’ve acquired a new story. Somebody always stops to lend a hand. Or to tell how their dad owned one just like it back in the day. Or just to gawk at the intrinsic spectacle the car creates, even unmoving.

My favorite anecdote about the Cadillac actually occurred when I wasn’t even around. An elderly woman happening by the shop insisted that she be allowed to sit in the back seat, because it’s the same type of car she went courting in as a young lady. I can just picture the mechanic, tatted up with arms like a linebacker, tenderly opening the door for her like a tuxedoed chauffer.

So the deeper gift the Cadillac has given me is perspective. Things make take longer than you like, you’ll probably experience obstacles, there may be times your goals remain stuck on the horizon.

But even when you’re trying and failing, that means you haven’t given up.

Having sworn off easy fixes, I’ve managed to take that longer view and apply it to other areas of life. I think I’m a more attentive husband and father. I made changes in my lifestyle and diet, and lost 30 pounds. I even upgraded my business attire, eschewing the polo-and-khakis of the marketing culture for suits, ties and vests. (Thus, my get-up at the beginning of this tale.)

In the end, I don’t know how much wisdom there is really to be found in purchasing dilapidated old cars. You could just as easily invest your time and emotions in coaching youth baseball, collecting Hummel figurines or crocheting horrendous sweaters. Our own version of truth is not something we find, but something we make.

But here is what I do know: When you’re feeling broken, find something you can fix.