COAL: 1953 Chrysler Windsor Convertible – Love At First Sight

1953 Chrysler Windsor Convertible

(first posted 5/1/2016)    When I turned 16 1n 1960, my mother took that afternoon off from her real estate job and waited for me to come running home from the school bus stop. We got into her 1957 Chrysler Windsor and she drove me to the NYDMV office in Garden City. After the necessary processes I walked out of the DMV with a New York State learner’s permit, unlocked the passenger door for my mother, got into the driver’s seat, adjusted the seat and mirrors, and drove home.

This was the beginning of my real life. Driving – legally – on public roads. No more back and forth runs in the family driveway and no more driving slowly around the parking lot of the Freeport Yacht Club when no one else was watching.

I had been saving up money for the time when I could buy a car doing odd jobs like mowing lawns, weeding gardens, paper routes, shoveling snow in the Winter, scrubbing boat hulls in the Summer, and baby sitting. Yes, baby sitting. It was good money and easy indoor work, and all I could eat from the fridge.

In 1960, 100 dollars could buy a reasonable vehicle if you weren’t fussy. I wasn’t too fussy, but I didn’t find anything that struck me the way I wanted to be struck. And, after selling my small boat and outboard motor, I had 300 dollars to buy a car.

One evening in late fall of 1960 I was walking along the dock in Freeport Long Island when it happened; I was struck. It was love at first sight. A pale yellow 1953 Chrysler Windsor Deluxe convertible.

1953 Chrysler Windsor Convertible from its best angle (IMHO). The V is wrong!

The car in the photos is from the Internet but it is the same make, model, and color as my first COAL. Only the V on the trunk is wrong. The pictured car is a Windsor flat head six as was mine. Someone probably replaced the trunk lid with one from a V8 model.

The top was down and it had a ”for Sale” sign on the raised rear windows.

$300 dollars.

This was fate. My heart sped up with excitement. We were meant to be together. What could possibly go wrong?

1953 Chrysler Windsor Convertible

After waiting for the owner to take delivery on a new red Triumph TR3 (which he let me drive), getting insurance, and license plates, and paying out the 300 bucks (one does not negotiate when love is involved), she was mine.

Chrysler Corporation was not famous in the post war years for styling and design. Their cars were often called tall, bulky, solid, and a bit stodgy. As CC’er jpcavanaugh wrote in 2009, Chrysler’s president and later Board Chairman K.T. Keller was quoted as saying “We build cars to sit in, not to pee over”.

Indeed, most Chrysler products of that era were stodgy. Except for mine. Mine was a sleek yellow beauty (apologies to Click and Clack of Car Talk). Perhaps not really sleek, and probably more cream than yellow after years of sitting in the paint fading sun, and some say beauty was only in the eyes of the beholder. But 60 years after that first meeting, I still feel a strange time bending sensation when I look at these pictures.

The car had a 119 hp flat head six. For years Chrysler used the flat head design in their lower status models like the Windsor. Starting in 1955, they went to all OHV V8s in the Chrysler brand cars.

1953 Chrysler Windsor Six Cylinder Flat Head Engine

This beauty had a M-6 Presto-Matic semi-automatic transmission. Chrysler’s semi-automatics were attempts to lure buyers who didn’t want to manually shift gears. But, the first thing you saw when opening the driver’s door was a clutch pedal, labeled “Safety Clutch”.

Chrysler Semi-Automatic Safety Clutch Pedal from Paul Niedermeyer’s August 29, 2012 CC Article


Chrysler products with the semi-automatic transmission did not sell well and I suspect the presence of a clutch (safety or not) had a lot to do with it. Or maybe it was the convoluted instructions of how to drive with a semi-automatic.

The shift lever looked like a standard three on a tree but it was really four on the tree, sort of. The gear lever would not go into what would normally be first gear. Reverse was back and up (that makes sense) and Low 1 and Low 2 were forward and up, while High 3 and High 4 were forward and down.

Chrysler M-6 Semi-Automatic Instructions.

For a better description of the Chrysler M-6 semi-automatic, see

Early Chrysler M-6 Semi-Automatic Shift Quadrant (R Lo Nu Dr).

My 53 Chrysler did not have a shift quadrant so it looked like a normal three-on-a-tree manual. Earlier models did have a shift quadrant showing the odd positions of “R Lo   Nu   Dr”.  This pattern probably confused potential Chrysler customers even more than the presence of the “Safety Clutch” and ultimately turned them into GM buyers.


1953 Chrysler Imperial shift quadrant from jpcavanaugh’s July 16, 2013 CC Article.

Later semi-automatic quadrant designs looked a bit more modern, if not exactly logical with a “R L   N   D” pattern, as on this 1953 Chrysler Imperial, shot by JP Cavanaugh..

The clutch was needed whenever you moved the shift lever. But, as long as you kept it in High, you could drive all day, stopping and starting and never touch the clutch. That’s because in front of the clutch and behind the engine was a fluid connector. Think torque converter with minimal torque conversion, just no direct physical connection between the engine and the clutch. That’s why it never stalled.

Note: Earlier Chrysler product fluid drives had no torque conversion at all. By 1953 there was some – just not much.

To drive from an idling position in neutral, floor the clutch and push the lever forward and down into High. Let up the clutch completely with the foot brake applied and the car would not stall; you were in High 3. Let go off the brake, step on the gas, and accelerate in High 3 to about 10 to 15 mph, release the gas completely, wait for a “clunk”, and then you are in High 4.

Stopping, or slowing down to below 10 mph, would cause the transmission to down shift into High 3 where the process started anew.

For more sprightly acceleration, you could access Low 1 and Low 2 by flooring the clutch and moving the lever up to where second would be in a three on a tree. Low 1 was a real stump puller and Low 2 was achieved by letting up on the gas and waiting for that clunk. Theoretically one can go through all four forward gears, but I found that using Low 1 and Low 2 usually resulted in a speed that brought forth High 4 when the lever was manually shifted. Starting in Low 1 and manually shifting into High usually brought forth High 3 and then the off-the-gas clunk into High 4.


1953 Chrysler Windsor Interior

I used the term “sprightly acceleration” above but that was relative to normal High 3 and High 4 operation. Old web documents say the flat head six cylinder Chrysler Windsor took 22.2 seconds to get to 60 mph. That was probably measured using H3 and H4 only. But even using the Low gears, flat head six cylinder Chryslers with the semi-automatic transmission were slow. In 1949 Tom McCahill, writing for Mechanix Illustrated, said that the 1949 Dodge with a semi-automatic transmission was a “dog”. A 1953 Chrysler convertible was even heavier than the 1949 Dodge, and probably slower.

A dog? Well, I love dogs, both then and now.

Three Dog Selfie. Marcelo (left), Benny (right), and me (middle).

Three Dog Selfie. Marcelo (left), Benny (right), and me (middle).


I never had any problems with that semi-automatic transmission. That’s more than I can say about a future 1995 Chrysler Eagle Vision TSi COAL.

Now that I had a car, I needed a better way to earn the funds to pay for its care and feeding. With my New York State working papers in hand I started working at Joseph’s Hamburgers on Sunrise Highway in Rockville Center at the rate of one dollar per hour (plus all the burgers, fries, and soda I could devour during my infrequent and very short breaks). The only rule we could not violate was that the rotisserie chicken pieces, fish cakes, and half pint containers of milk were off limits. The consequences of violating this rule were too awful to discuss.

I passed my driver’s license road test on the second try. I failed the first road test because I let the non-power assisted steering wheel of a 1953 Packard spin back between my fingers to top dead center after making a turn. Lesson learned, don’t be a smart-ass show off. Try number two was on a full power 1957 Chrysler with careful hand-over-hand wheel returns.

In late summer of 1960 I had a New York State junior driver’s license; that meant no driving at night. I also had a dollar an hour job and needed as many hours as possible to stay in the black. And as the new guy I got the worst hours, weekday and weekend nights. OK by me, I had a very quiet social life.

For the typical summer night shift, I drove the Chrysler to Joseph’s in the early evening, put on my white uniform and paper hat, and got to work. Closing time was around 2 A.M. and cleanup took about 2 hours – give or take. Then the night manager, Joseph’s son Andrew, would pile the crew into his 1959 Pontiac Bonneville four door flat top and take us to the 24 hour Pantry Dinner just down the block. When you have been eating triple nickel burgers all week, eggs over easy with home fries tasted like heaven.


Night Manager Andrew’s 1959 Bonneville Four Door Flat Top. Breakfast road trip.

Night Manager Andrew’s 1959 Bonneville Four Door Flat Top. Breakfast road trip.


The Pantry Diner in Rockville Centre Long Island

The Pantry Diner in Rockville Centre Long Island


When breakfast was done and the sun was just coming up, Andrew dropped me off at the now close burger shop, I got into the big yellow Chrysler, and drove home. Legally.

My sleek yellow beauty had a few issues.

As soon as I had it registered and tagged, I proudly invited two of my friends for a ride. I twisted the handle at the center of the top right above the windshield, climbed into the rear seat and unzipped the plastic rear window, got back into the front seat and turned the top’s switch to “down”. The big black top rose up and away from the windshield and folded itself neatly behind the rear seat.

That was the last time the top motor worked. Ever.

To get the top back up I had to drain the fluid from the top’s hydraulic system. This required crawling into the trunk, removing a panel, disconnecting the fluid lines from the pump, and catching the fluid in a can. I spilt about as much fluid into the front of the trunk as I recovered. In 1953, Chrysler used DOT3 brake fluid in their top hydraulic systems and brake fluid had a lot of alcohol in it. For the next four and a half years the car’s interior had a slowly fading aroma of brake fluid. Some wags said it smelled like stale cheap beer.

The Chrysler’s top was now manual. To put it down, I pushed the top up and back until gravity grabbed it. To put it up I stood in the middle of the back seat facing to the rear, grabbed both sides of the top, pulled up with a non-insignificant amount of effort, and then slowly fell backwards over the front seat while still holding onto the top. Then I pulled the top down onto the three spikes and locked it in place. Not so bad, just a bit embarrassing if anyone was watching.

Wait until this guy tries to get that top up on his 53 Windsor Convertible!

Wait until this guy tries to get that top up on his 53 Windsor Convertible!


Then the gas gauge gave out. One day it read one-third full after a fill up. I squeezed myself under the steering wheel with my legs in the air and used a flashlight to look at the back of the fuel gauge thinking maybe there was something easy to fix like a loose connection. Yea right. I did not see anything “user serviceable” but I did discover that this head-under-the-dash and feet-over-the-seat position really felt claustrophobic. It freaked me out and I scrambled out as quickly as I could to avoid panic.

The solution was simple, set the trip odometer to zero whenever I filled the tank and subsequent fill ups were based on trip miles. A car owner’s version of Occam’s razor.

Four Gauges Surround the Speedometer. Three Work.

Four Gauges Surround the Speedometer. Three Work.


I also discovered that the convertible top was not quite weather tight. After a windy snowstorm I opened the driver’s door to find a peaked drift of frozen white powder that ran from the base of the securely closed driver’s window to the bottom of the front passenger seat. I brushed it out so I could drive to school but much of it remained around the floor. The thick carpet underlining got wet, and while I used sunny days to try and dry it out, the interior smelled of mildew.  And brake fluid.

So, my automotive object of love had a few problems, a non-operable top motor, a non-operable gas gauge, and a vulnerability to the elements of nature.  Not so bad.

Also the plastic rear window was as opaque as a cheap plastic shower curtain. That was a safety issue. I would need to look into that.

And there was a slow oil leak at the main seal between the engine and the fluid drive. This was engine oil that could be easily monitored and replenished, so I wasn’t planning to do anything about it at that time.

And the big tube radio that slammed the battery gauge to negative whenever it was turned on and threatened to drain the 6 volt battery at every stop light (this car had a generator rather than an alternator) did not always turn off when I pushed the OFF button. So, turning off the radio required a careful hand shaded look in daylight to see if the dial light was truly off.

1953 Chrysler Radio. That off button didn’t always mean off.

1953 Chrysler Radio. That off button didn’t always mean off.


Again, not so bad.

Also, the car came with two old style bald snow tires on the rear. Not safe. I got four new bias ply black wall tires shortly after I bought the car and later spiffed them up with two fake wire wheel hubcaps that a friend discarded. I could only find two.

Also, rust bubbles started appear on the left rear fender just above the wheel. I would need to look into that.

But, love is blind and car love is deaf, dumb, and blind. This magnificent machine was all mine, warts and all.

The big yellow Chrysler would soldier on as my pride and joy ride for the next four and a half years. Despite her initial list of mechanical issues she always ran quietly and competently, never developed any additional problems, and never left me stranded as I finished high school and started as a commuting student at Adelphi University.

One memory involving this COAL does stand out. In the summer of 1962 after graduating from high school and getting ready for college I met a girl at our church. Judy was tall and slim and beautiful with big brown eyes and long brown hair.  As Lord Byron might say (and he did): “She walked in beauty like the night”.

It was love at first sight; obviously not an unusual occurrence for me.

I asked her out for a date and she said yes. I wasn’t expecting that. Tall skinny guys with thick glasses, curly hair, and who smelled faintly of cheap hamburgers, mildew, and brake fluid did not have much success with girls. Think modern day geek but without the smarts.

I figured we’d go to a movie so I looked up what was playing and where and picked Judy up at her home. As we drove in the direction of the theater we discussed the big news of the week, the death of Marilyn Monroe. Newspapers said it was a suicide. Judy and I could not understand why someone so famous, so beautiful, and at the top of life’s ladder could choose to die. What was there about life that could make a person do such a thing.

A movie did not seem to be mood appropriate; I suggested we drive down to and along the ocean. Judy nodded. We turned onto Meadowbrook Parkway south towards Jones beach and then east onto Ocean parkway with the foaming ocean on the right and the bay on the left. Although it was summer it was a cool by the shore; the windows were rolled up, the heater was on low, and the only sound was the thump thump of the tires on the road’s concrete divider strips. We talked softly about life and tragedy and where we were going in the future and what we thought would happen there.

At Captree State Park, we got out of the car and watched the rolling surf.  A cold damp salty air was blowing in from the ocean and we could feel the salt on our faces. We returned to the car, and headed back west on Ocean parkway, now with the ocean on the left and the bay on the right.

I realized Judy was sitting next to me, very close to me. That was a universal sign in those innocent teenage times and pre-seatbelt days of, what, something wonderful and warm and accepting. It’s hard to put into words just how serene and sharing that moment felt. We did not talk. We just sat close together in that big yellow Chrysler thinking to ourselves about life and loss as we listened to the tires on the pavement strips and Frank Ifield’s “I Remember You” on the AM radio turned so low it was barely audible.




Be back soon with the next COAL.