Postmasters, Backroads, and the Buick That Knew Too Much

In 1992, I was 15 years old—too young to drive legally, too old to sit quietly in the backseat, and just the right age to be handed a wildly irresponsible level of trust by my father.

Dad had just landed the gig of a lifetime—Postmaster. After years of managing mail carriers, dodging union beefs, and making sure no one parked a Grumman LLV in a ditch, he was finally getting the keys to his own little federal kingdom. So naturally, He celebrated. The party was in New Windsor, NY, and it had all the energy of a retirement bash crossed with a dive bar karaoke night—except Dad wasn’t retiring, just getting promoted. Which somehow made it rowdier.

Now, my old man wasn’t the kind of guy to sip a light beer and call it a night. He was deep into the celebration, nursing a buzz that couldn’t drive, let alone pass a breathalyzer. So when the time came to head home—nearly an hour away—he looked at me and said something along the lines of, “You’re up, kid.”

Let me be clear: I had no permit, no license, and only slightly more fear than common sense. But in my defense, I’d been driving since I was 10—firewood roads, old pickups with clutches held together by rust, logging trails that would make a Subaru cry. By 12, I was casually moving bulldozers and backhoes around like a union operator. So sliding behind the wheel of my mom’s Buick Regal station wagon? Piece of cake. Giant, Beige , rear-wheel-drive cake.

So I slid behind the wheel of my mom’s Buick Regal station wagon like I’d done it a thousand times. My feet barely reached the pedals, and the bench seat was pushed up so far I was practically in the glove compartment.

Dad stayed awake at first, pointing out turns and landmarks like a chatty drunk Garmin. “Watch the bend by the diner... you’re gonna merge onto 17K... don’t go past the road with the tractor on the mailbox.” Then, somewhere outside Montgomery, he went silent. A mid-sentence nap like only dads can pull off. Head back, mouth open, the faint sound of a snore echoing against the fuzzy velour headliner.

He dozed off about 20 minutes in. Head tilted back, mouth slightly open, arms crossed like someone sleeping through church. This was the moment I realized I had full control of the car and no adult supervision.

I should’ve tossed him a can of beer and said, “Here, throw this out the window before we hit a checkpoint.” It would’ve been fitting. But instead, I drove. Like a stone-cold professional. I kept that Buick between the lines like it was my job and Alan was my drunk co-pilot.

As we got closer to home, somewhere up in the Shawangunk's’ foothills, he stirred, gave a grunt, and pointed me toward a shortcut—back roads down the side of the mountain. Because obviously, that’s safer. Winding, dark roads with no shoulder, where deer run out and old refrigerators get dumped.

Finally, about a half mile from home, he had me pull over.

“I’ll take it from here,” he said, lighting a cigarette like he’d just finished a shift on the flight deck of an aircraft carrier. He drove into the driveway like nothing happened. Not a hair out of place. Because if my mom had seen me behind the wheel? There’d be a second going away party—this time for his funeral.

Sometimes fatherly wisdom comes in the form of whispered directions, a lit cigarette, and the unspoken agreement that what happens on Route 17K stays on Route 17K.