Thirty years after the fact, my older brother still likes to remind everyone that I managed to blow a full-ride scholarship my first semester at college even though I was supposedly “the brains of the family.” I think he enjoys telling the story because, at the time, he believed it was a flaw in my armor, a chip in the chrome plating. But even then, he must have thought I would do well for myself. Otherwise, he might not have made a deal that ultimately brought him to my doorstep with a Harley-Davidson Heritage Softail in the spring of 2018.

Along for the Ride, A Few Lengths Behind

In my office, I have a framed picture of my brother, age 5, and a chubby 2-year-old me. We’re wearing matching striped railroad overalls with thick leg cuffs, holding hands, and I have a big smile. I’ve always looked up to my brother. He was the epitome of cool – as soon as I knew what “cool” meant – even if he wanted nothing to do with his younger, dorky brother as we got older. If anything, that made him cooler.

Even in our teen years, when he was getting in trouble and I was getting straight A’s, I watched him admiringly from behind my textbooks, wishing I were as fearless and willing to take risks. 

A few years later, I ended up following him to the local college. With my grades, I could’ve gone somewhere more prestigious, but in my senior year of high school I had started hanging out with my brother and his friends. I was welcomed into his fold. We were friends again, like we hadn’t been since childhood.

I followed him onto the ski slopes – down mogul hills and over cliffs I probably shouldn’t have. When he got into motorcycles, starting with a Yamaha V-Max, I followed him there too. My first bike was a Honda V65 Magna. It’s a miracle I didn’t kill myself, but maybe I just didn’t have it long enough. I only owned the bike a little over a year before I had to sell it.

Here’s where the details get fuzzy. But it was college after all.

In my recollection, around this time my brother offered me a deal: Whoever could get himself a Harley first would then get the other brother one when he could reasonably afford it. The benefit of this deal was each of us eventually having at least one bike, either bought ourselves or gifted to us. But if we were both successful, we would each ultimately have two bikes.

When he bought a Sportster 1200 – and started doing pretty well in the business world – I got excited, especially as I was still screwing around somewhat aimlessly (this was after blowing that scholarship). Certainly my bike wouldn’t be far off.

Then he got a Fat Boy, and I thought, “Wait a minute.”

Turns out, my brother remembered the deal differently.

Deal or No Deal

By his own admission (when I called to tell him about this article), my brother proceeded to customize probably five other Harleys.

Several years and motorcycles later, after a few beers, I asked him about it.

“That wasn’t the deal,” he said. “It was that we both get one for ourselves first and then one for the other brother.”

“What if one of the brothers never ended up being able to afford one for himself to begin with?” I said, still living paycheck to paycheck at the time.

We continued to debate the finer details of a deal made about 15 years earlier. At the end of the night, I didn’t think I convinced him I was right – that kind of victory over an older brother is rare. But in 2018, after selling his business in a lucrative deal, he called me and said, “So, do you want a Jeep or a Harley? But whatever you pick, I get to choose the style.”

Who was I to argue?

I chose the Harley, and a month later, he showed up towing a 2004 Heritage Softail Classic with just over 8,000 miles. Talk about feeling like a kid again. Or at least that carefree 20-something-year-old. It was a dream – and a deal – come true.

Sometimes I wonder if my brother made that original deal because he felt bad that I had to sell my motorcycle. He says he just thought I would hit it big before him and things would’ve gone the other way. Funny how life works.

Whatever his reasons, he came through. These days he doesn’t ride anymore. After selling his business, he moved to Hawaii and traded his jeans and riding jacket for a wetsuit and fins. But after all these years, he is still the epitome of cool.

This article first appeared as the Exhaust Note feature in the October 2022 issue of Rider.

The post A Tale of Two Brothers and a Deal for a Harley-Davidson first appeared on Rider Magazine.
Source: RiderMagazine.com