A Tale of Two Brothers and a Deal for a Harley-Davidson

Exhaust note Harley-Davidson deal
The author and his brother (right) weren’t always this close. But time –and a Harley-Davidson –heals all wounds.

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 probably 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.


  1. I never had the chance. By the time I could afford the years long wait I’d always dreamed of, that being able to ride together on our own Harleys, my older brother passed away. I’ve always felt like so many others that have stayed alive after a siblings death,…What if I’d done this or that he’d still be here to fulfill our dream. I think I’ll get some earth from his grave site and seal it up in a gremlin bell so whenever I ride he’ll be there with me.

    • Robert, I’m sorry to hear you missed your opportunity. It sounds like you had some similar issues with your brother that mine and I have had over the years, which I can see might make it harder in your case now that he’s gone. I think that’s a cool idea about the gremlin bell.

      Thanks for commenting (and for reading Rider, of course).


  2. Everyone a story. First Harley at 26, lasted six months first a divorce, raise kids, leave kids, turn 57, than the slim showed up, and now at 59, I’ve also a sportster to, and i ride it to work, three miles up a mountain to work, three miles home. Lol I work at a ski resort.

    • Jeff, thanks for sharing your moto-history. As I think about the road up to our local ski resort, I think you’re a braver man than I am 🙂

      Keep the rubber side down!

  3. This is a great article and the feelings expressed by Mr. Dail resonate for a number of reasons. I never had a brother and worse still, I was the youngest member of my family during that generation with two older sisters. So, while I always wanted a Harley Davidson, being raised without access to such extravagance and marrying young with four children that followed, it hasn’t yet panned out.
    My hope is to find a 2001-2010 heritage and make it my own with Vicla styling throughout. It will take some time but I still hold a glimmer of hope!
    Thanks for the article.


    • James, you gotta keep that hope alive. As the parent of a couple younger children myself, the reality is that I still might not have one either if it weren’t for my brother making good on this deal. Now that I have one, it’s a case of making myself skim over the posts selling other ones, thinking “Hmm, I could probably take that much out of savings.” 🙂

      Anyway, I’ll visualize that bike with you, and hopefully it will help make it a reality sooner than later. Thanks for commenting (and for reading Rider, of course).


  4. My first harley i was 19…sporster 1000 iron head.l loved that bike i rode a lot of girlfriends in short time i rode it.had bad spill left turn driver made a law breaker turn.no left..but 8 bikes later traded in a honda 750 for a soft tail standard.107. At 58 im having a blast.rode mts. in va.sc. ga.

    • M.smith, thanks for the comment. It’s great hearing how many people still fondly remember their “first.” And glad to hear you’re still having a blast in those mountains. Ride on!


  5. Such an engaging story of brotherhood and passion for Harley-Davidson! This tale beautifully captures the essence of family bonds and shared dreams. It’s heartwarming to see how their deal for a Harley turned into an unforgettable adventure. Truly inspiring!


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