Cowboy & Indian Summer Event Tour—The Final Roundup
The inventor of “Gonzo” journalism, the late Hunter S. Thompson was one of my early professional heroes. Thompson was unconventional and often unhinged—the guy did a lot of drugs on assignment—but he never failed to bring home a story that made you feel as if you were there with him. So much of daily reporting comes down to the who, what, when and where of traditional journalism, and that is what the job requires. But to experience events as one of their legitimate participants and bring home that kind of story, you have to become one of them.
You have to immerse and imbed yourself.
As it turned out, the DCB Owners Regatta—rather than the Florida Powerboat Club—would be the author’s last adventure of the year in Cowboy & Indian. Photo by Tom Leigh copyright Tommy Gun Images.
Thanks to Kelly O’Hara and Kiran Pinisetti, the owners of the Cowboy & Indian DCB Performance Marine M37R catamaran with two Mercury Racing 500R outboard engines, that’s exactly what I mostly did during the 2024 boating-event season.
From the first moment I saw the 37-footer during Mercury Racing’s June 2023 debut for the 500R package in Charleston, S.C.—Cowboy & Indian was on display and available rides during the event—I fell in love with it. I was drawn to it.
Brothers in arms, O’Hara and Pinisetti make co-owning an exotic high-performance look easy. Photo by Matt Trulio.
And that gave me an idea. Go Gonzo style and cover much of the 2024 event season from that boat. The only hurdle? Getting permission from the owners to join them. That turned out to be a low leap. Pinisetti and O’Hara were game for an adventure, even with a quirky-as-hell and at times all-thumbs reporter.
We started as acquaintances, then became friends. Some six months and 10 events later—the Kuttawa Cannonball Run in Kentucky, Hartwell Lake Charity Fun Run in South Carolina, Bago Big Bet in Wisconsin, Boyne Thunder Poker Run in Michigan, 1,000 Islands Charity Poker Run in New York, the Pirates of Lanier Poker Run in Georgia, the Rock The River Fun Run in Ohio/Kentucky, Lake Powell Challenge in Arizona/Utah and the DCB Owners Regatta in Arizona—we became family. I know O’Hara wife, Julie, and Pinisetti’s wife, Jessica. I’ve stayed in their homes.
Even miserable weather could not keep Cowboy & Indian off the water during the inaugural Bago Big Bet event in Wisconsin. Photos by Pete Boden copyright Shoot 2 Thrill Pix.
I know the O’Hara’s dog, Sally, who is more at ease on a boat than most humans.
Three basic skills I learned from the experience: 1. How to re-buff a hull-side after O’Hara, a noted perfectionist, kindly critiques your work. 2. How to cover a 37-foot catamaran loaded on a tilt trailer. 3. How to pick up meal tabs to avoid feeling like a total parasite.
But the biggest thing I learned is what it really takes in terms of commitment, time and resources to haul a catamaran to events around the country, several of which happened on back-to-back events in different states, and participate. If you are not a go-fast boating fanatic of means, the event-schedule of O’Hara and Pinisetti event-schedule (at least it was this year) is not for you
Kelly O’Hara and Kiran Pijnisetti brought their spirit animals to the Lake Powell Challenge.
We experienced plenty of highs such as cruising Lake Powell at 90 mph in a delightful haze of sensory overload and trading endless puns with O’Hara during every event while Pinisetti’s eyes rolled like a ball on a roulette table, and zero lows. Even leaving a Cincinnati restaurant to find an empty space where Pinisetti had parked his truck led to a fine story and a lesson in what you probably shouldn’t do if you vehicle gets stolen.
At least if personal safety is a priority.
Extended family is the family you choose, such as (clockwise from left) Jessica Pinisetti, Sally the Wonder Pooch (held by the author), Julie O’Hara, Kelly O’Hara and Kiran Pinisetti. Photo by Pete Boden.
Cowboy & Indian will exit the past two seasons having covered more than 6,000 miles in 200-plus hours. Pinisetti estimate that I spent more about 100 hours running with them. Want to know the best seat in the boat, other than those for the driver and co-pilot? Ask me sometime.
Our final adventure together in Cowboy & Indian was supposed to be the Florida Powerboat Club Key West Poker Run last week. But the Tropical Storm Rafael had other plans. Pinisetti and O’Hara made it Wednesday as planned, but their 37-footer did not. I came down Tuesday with club president Stu Jones on this Cigarette Racing Team 38 Top Gun. Still, we met for an intimate farewell dinner on Wednesday that started as just the three of us yet ended up as a party or 11.
Friday’s trip to Sleeping Bear dunes during the Boyne Thunder Poker Run in Northern Michigan was among the highlights of the tour.
But like my hosts for a season of events I will never forget—and for which I will always be grateful—everyone at the table was family.
I started as a reporter looking for immersion in his subject and an adventure. I finished as a member of a tight-knit boating family. Story endings don’t get any better.
The Cowboy & Indian last supper in Key West included (clockwise from left) Blake Mahieu, Christy Foote, Yvonne Aleman, Crystal Brasher, Ray Brasher, Kiran Pinisetti, Grover Alcock, Kelly O’Hara, Matt Trulio, Greg Harris, Chris Fisher, Shane Mahieu.
Related stories
Cowboy & Indian Summer Tour, Part IX—Road Family
DCB Owners Regatta A National ‘Family’ Reunion
Cowboy & Indian Summer Tour, Part VIII—On Sacred Water
Cowboy & Indian Summer Tour, Part VII—The Rides That Matter
Cowboy & Indian Summer Tour, Part VI—Enter The Back-Up Boat
Cowboy & Indian Summer Tour, Part V—Look Mom, No Truck
Cowboy & Indian Summer Tour, Part IV—The Homecoming
Cowboy & Indian Summer Tour, Part III—Umbrella Coverage
Boyne Thunder 2024 Day 1—A Lunch, A Party, A Dog Named Sally And A Cold Shower
Commentary: When Go-Fast Boating Guys Have Too Much Time To Kill
Cowboy & Indian Summer Tour, Part II—No-Wake Zone Confidential
Cowboy & Indian Summer Tour, Part I—Standing On The Shoulders Of Giants In South Carolina
Pirates Of Lanier Charity Poker Run Weathers The Storm
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