Gringo was the second Softail Heritage I’ve owned, the third time I bought one. That’s because I bought Pretty Boy Floyd twice.

The first time I bought Floyd, it was brand new. The second time, five years later, it had about 12,000 miles on it. I would go on to own four different versions of the Heritage.

This is how that happens.

One day, I buy a Softail Heritage, the most beautiful bike Harley makes. Although it does not lean much, I love the bike. It is the perfect motorcycle. It glides. It’s balanced. It’s a work of art. I am a happy motorcyclist. I ride it everywhere. Nice and slow. I pose it for pictures. Because riding is about the moment, about the sights, about the scenery and the people, not about making the asphalt wiz past you as fast as possible.

One day, in my rear view mirror I see a Ducati gaining on me. Rapidly.

By the time I get home, the Heritage Softail is too slow, can’t lean to save its ass, uses ancient technology, makes me look like an old man, and is probably about to break down. What was I thinking when I bought it?

So I sell the slow-ass Harley and buy myself a Ducati. This is my 2005 999S:

Few motorcycles are as visually intoxicating as a Ducati.

Above is the 2019 Monster 1200R that I owned a few years later. Over the years I would go on to own an embarrassing number of Ducatis.

You see, when I turn the key on a desmo 4-valve engine with the 41 degrees of overlap, that heavenly engine explodes, pounds, burbles, and gurgles in a symphony that’s part Ode to Joy, part Stairway to Heaven.

When I throw a leg over the saddle and ride it, I transcend this earthly plane.

Soon I’m looking into track days, fitting myself for track leathers, painting half my face red, and learning Italian. Milano, eccomi!

Yes, the riding position is tiring, but I resolve to do more push-ups. Yes, my teeth hurt after a long ride, but I resolve to do more sit-ups. When I wind up riding for 7 hours because I took a wrong turn somewhere near Breckenridge, I lie down on the garage floor and beg God to forgive my sins.

A few weeks later, while I’m rubbing my back at a stoplight, a guy on a BMW GS looking like his mother dressed him pulls up beside me. He nods at me kindly. I ignore him, lean down, grab the bars, and blip the throttle. When the light changes, I drop him. He hasn’t even shifted into first gear by the time I’m dragging my knee across the asphalt at the next curve.

I cackle inside my helmet.

An hour later, I’m lying across a barrel at the local filling station, a little old lady beating my back with a cane because I paid her $20.

Between moans I hear the mumble of a boxer engine approach. The Momma’s boy parks, jumps off the bike, gives me a cheerful greeting, and walks inside. When he returns, he hands me an ice cold water bottle.

Turns out he’s ridden 600 miles already, wants to get in another 300 by nightfall so he can complete his Iron Man 1500 Bun Burner. It’s a warmup for his trip to the Arctic Circle later this summer. He asks me if I know of a gym nearby where he can hit the weights before continuing.

Next day, I’m trading in my miserable, impractical, poser Ducati for a brand new BMW R1250 GS.

The GS can stay with the Ducati or any other sportbike under most street riding conditions. Electronic this. Lean-sensitive that. Active cruise control. Soon I’m strafing asphalt with my left hand on the bar, my right hand around a stogie, the GS electronically maintaining a safe distance from the bike in front of me. I might even google “Multitasking on a motorcycle” for suggestions.

A couple of months later, I don’t understand why I’m just not that into riding anymore. I’ve strafed all the good spots within a day’s ride. I’ve taken long multi-day rides in total comfort. I’ve explored some local dirt roads. It was a lot of fun the first time. Not too bad the second time. But I’m just not that into riding anymore. Something is missing.

And then, because there is a God, I see glinting in the sunlight the most perfect motorcycle ever made …

A week later I got rid of that boring-ass BMW, bought myself another Softail Heritage, and I feel ALIVE again. ALIVE!

I hum me some Lynyrd Skynyrd as I polish that chrome, wax the paint, and lovingly clean each and every spoke on those wire wheels. Life is good again. I’ve been given a second chance. I have no idea what the heck got into me, and I swear, with the conviction that only a returning Harlista can understand, that now that I’m home again, I will never, ever, under any circumstance, let that happen again. Ever. No matter what.

And then …