In Boat Rodeo, You Don't Need a Horse to Be a Cowboy
The Chesapeake Cowboys are a subculture of boat captains who technically compete for money, though it's really all a matter of pride.
Jamie Marshall backs out of the slip as thousands of spectators, including a local television station, a documentary filmmaker, and a YouTube streamer, all vie for the best view. Die-hard fans who arrived three hours early watch from folding chairs at the water’s edge, while others cram shoulder to shoulder in the dock bar, crushing cans of Miller Lite as the smell of fried seafood wafts over the Wicomico River.
This lean, waggish 48-year-old, is a member of the Chesapeake Cowboys, a subculture only found along the shores of Maryland and Virginia. In it, captains compete to dock their Chesapeake deadrises—workboats characterized by sharp bows and flat open cockpits— in reverse as quickly as possible. Winners of these so-called boat rodeos can take home anything from a few hundred bucks to seven thousand dollars, though it’s really all a matter of pride.
Marshall’s been competing since his 20’s, and he knows today’s course is a tricky one. To win, he’ll need to round a bend that circles an overwater section of the dock bar, overcoming a blind spot at speeds that can reach a little more than 25 miles per hour. And he’ll have to do it quicker than his biggest rival, Derrick Hoy, who’s already idling and waiting for his turn.
“You’re multitasking, dealing with the throttle, the clutch, and you have to keep an eye on your person throwing the loops so they don’t fall overboard,” Marshall says. “The prop underneath is spinning, and it could kill you.”
When it comes to boat rodeos, every second counts. One mistake can mean overshooting the slip or a crashed piling. At last year’s competition, Hoy even clipped the corner of the bar. Although no one was hurt, that ill-fated run quickly became the stuff of legend, racking up millions of views on TikTok.
But Marshall isn’t worried.
“I never practice, it’s all about knowing your boat,” he says. “It’s like riding a bicycle.”
Boat racing competitions have been ingrained in the culture of those who work the water since at least the 19th century. From 1921 to 1931, the Baltimore Sun sponsored the Chesapeake Bay Championship Workboat Races. And in 1947, the town of Crisfield, once known as the “crab capital of the world” began hosting the National Hard Crab Derby, a weekend-long celebration with crab races, crab picking, and a Miss Crustacean contest. Competitive boat docking was added to derby events permanently in 1971. The National Hard Crab Derby was just one of many watermen festivals held on Maryland and Virginia’s eastern shores, where entire communities are built around oystering and crabbing. Watermen’s Appreciation Day, held every August in St. Michaels, is one such festival that has become a mainstay, with competitive boat docking as a headlining event.
In 1994, Erik Emeley, a waterman from Crisfield who also owns a tiki boat business, formally coined the group of competitors, ‘The Chesapeake Cowboys.’ Emeley, who goes by the nickname “Flea,” took the group on the road, expanding from local festivals to dock bars up and down the Chesapeake coast. With his signature straw hat and Eastern Shore drawl, Flea acts as MC at every competition, encouraging a party-like atmosphere as he pumps up the crowd in between events.
There’s only one prerequisite to becoming a member of the Chesapeake Cowboys: competitors must be licensed watermen, a regional term used to describe crabbers, oystermen, and fishermen. And for the Cowboys, winning is about taking pride in what’s typically backbreaking work with low pay, constantly fluctuating governmental regulations on how much you can catch, environmental challenges, fickle weather, and the sheer unpredictability of the harvest.
It would be easy to paint them as beer-guzzling rednecks tearing up boats, but that doesn’t tell the real story.
For Marshall, competing with the Chesapeake Cowboys was a no-brainer. He grew up on tiny Smith Island in the Chesapeake, the son of Dwight Marshall, who was the winner of the first official boat docking competition in Crisfield in 1971. He worked as a crabber in his 20s before joining the police force. Now he owns a marine repair business and consults for the Coast Guard Investigative Service (CGIS), where he most recently helped investigate the Key Bridge collapse.
In fact, a Marshall has been competing every year since the boat rodeos began. And 16-year-old Seth is the latest in this esteemed lineage. “He did well this past week at Crisfield,” Marshall says of his son. “I could see in his eye that the bug got him."
Derrick Hoy leans against the cabin of his 30-foot Calvin Beal, the ‘Crusher,’ awaiting his turn at a run. Sporting wraparound sunglasses and a Huk fishing cap, the 53-year-old fisherman works the water year-round, oystering near Ocean City in the winters, and scalloping off Cape Cod in the summer. He spends his late summer weekends on his home turf, running boats with the Chesapeake Cowboys. Hoy’s unassuming nature is typical of someone who spends his days hundreds of miles offshore, but his mellow, easygoing manner shouldn’t be mistaken for apathy. For Hoy, it’s about being the best, and maybe beating his longtime friend and competitor, Marshall.
“Jamie and I, we’ve known each other forever,” he says. “We both want to win, but I’m not going to give it to him.”
Hoy lines up for his practice run, calling out to his rival that he’s holding up the line. But as Marshall puts his boat into gear, he hears a crack and a bang. His boat stalls, stranding his 30-foot Sisu, the Heather Nicole II, mid-channel.
“He’s run his shaft off!” another captain calls out, referring to the mechanism that spins the prop.
With his propellor off and his boat immobile, Marshall is out of the race before it’s even begun. A $5,000 fix is in Jamie Marshall’s future. And that’s one of the many pitfalls of competitive boat docking—sometimes winners take home just enough prize money to keep their boat afloat.
Marshall is towed back to shore by another boat, handling his loss with humor and grace. “At least today I’ll get to watch for once,” he says, taking a seat in the crowd.
Flea gathers the masses for a 9/11 tribute and welcomes a local singer to perform the Star-Spangled Banner. “Gentlemen, and ladies, start your engines!” he hollers into the mic. The crowd roars, hoisting cocktails and raised fists.
The rodeo has begun.
With his main competitor out of the contest, Hoy rounds the corner at a tight angle—missing the bar this time—to the shouts and cheers of the crowd. He throttles hard, turning the boat and slams it into reverse before crashing to a halt, spraying the crowd with his wake. He tosses one lasso, then the next over a piling before the clock stops, recording 22.36 seconds—the fastest in the small boat category.
From his seat in the crowd, Marshall leaps up and cheers. It’s clear any rivalry that existed between him and Hoy has long since dissolved.
Marshall’s easy transition from competitor to comrade is unsurprising. Indeed, the small, close-knit community of watermen is at the heart of every competition. There aren’t very many of them, with a population shrinking in numbers every year, as fewer enter the profession. They stick together, knowing that even in the heat of competition they have each other’s backs. Every Chesapeake Cowboys event includes a fundraising aspect, whether for a waterman in need, or a local organization like the town’s volunteer fire department.
“We look out for our own,” as Marshall puts it.
But the rodeo isn’t over yet. Up next is the shootout—a final showdown that allows boaters to beat their earlier times. It’s easily the most dramatic event of the day because it allows for stunning comebacks.
Before the shootout begins, Derrick steps off his boat, approaching Flea at the mic. Grinning, he issues a challenge that elicits whoops from the crowd. He wants Marshall to take a shot using his boat, the Crusher.
“I don’t want anyone saying I won because Jamie couldn’t compete,” he announces.
On board the Crusher, Marshall acclimates himself with the boat, noting that everything, from the steering to the throttle, is laid out opposite to his own boat. Docking a boat at high speeds is all about muscle memory and knowing your own vessel. His goal is to give the fans what they want—and hopefully not tear up his friend’s boat in the process.
With the challenge accepted, the crowd is buoyed and wolf-whistling.The DJ turns up the country music, while Flea passes a bucket of money to sweeten the pot for the winner. Spectators, well-greased from an afternoon of margaritas and 90-degree heat, ask each other, ‘Who’s it gonna be? Jamie or Derrick?’ A group of older men in the VIP section absorb the scene with glee. After all, they drove seven hours from Cleveland for exactly this.
Marshall’s turn in the shootout is finally up, and the Crusher comes barreling around the bar at top speed. He brakes hard and throws it into reverse, overshooting the slip by several feet. The crowd lets out a collective sigh of defeat.
It really is all about knowing your boat.
Hoy’s turn sees him coming in hard on the Crusher, reversing at breakneck speed and splashing the crowd with a massive wave. He tosses both lassoes on the pilings and clocks in at a staggering 20 seconds flat. The crowd erupts, including Marshall who pumps his fists at his friend, the clear winner of the day.
The fans disperse, though the party will continue at the dock bar well into the night. Marshall weaves through the crowd, climbing aboard the Crusher. “You got me!” he says to Derrick and slaps him on the back. After some friendly ribbing and promises for a rematch, they pose for a photo, two proud cowboys for whom boats are not only a means of livelihood, but an extension of their identities.