Orient Point is a quieter, calmer fishing hub than often-chaotic Montauk, but my sense of tranquility faded with the morning haze as we approached the striper grounds known as “The Race” aboard the Nancy Ann IV, captained by Richard Jensen.

Race Reef is situated between Little Gull Island and Fisher’s Island. It’s approximately 3½ miles wide and creates a fast-moving rip due to the drastic differences in bottom contours. Along with rapid current, large boulders make this a difficult area to fish productively without snagging bottom. To effectively fish these waters, captains developed a modified three-way rig, with a bucktail jig instead of a bait and beefed-up hardware. The aptly named “Orient Rig” has been a big bass catcher for years and is responsible for a number of legendary stripers, including a 73-pounder caught by the all-tackle striped bass world-record holder, Greg Myerson in 2013.

Myerson’s whopping striper was caught in the eastern Long Island Sound, not far from the rips of The Race where I was headed with Captain Jensen on that late-June morning. Since 1960, Jensen and his wife, Nancy Ann, have operated fishing charters from the North Fork of Long Island. Jensen is a third generation full-time fishermen, and he knows these waters like the back of his hand.

As we reached the white caps of The Race, our mate, the captain’s son and fourth generation fisherman, Rick, divvied up Nancy Ann’s pre-rigged Lamiglas BL 7030 boat rods. These moderate-to-fast action blanks are rated for weight up to 6 ounces, but can handle heavier loads with relative ease. The conventional reels matched to the rods were spooled with 30- or 40-pound-test moss-green braided line. The braid’s slim diameter is essential for fishing this deep, rock-laden area. My gaze then landed on a large, 5/0 3-way swivel that dangled from the mainline as it awaited the finishing touches to complete the rig. I learned later that smaller swivels are prone to bending under the strain of heavy bass in ripping current.

To one of the open swivel eyelets, a 10-inch length of 100-pound-test monofilament was tied, leaving a surgeon’s loop knot for a sinker. The heavy leader keeps bothersome bluefish from chomping through the line, saving sinkers for another day. The ones used at The Race ranged from 10 to 16 ounces, depending on the speed of the current. Such heavy lead was necessary for keeping a presentation near the bottom in 100 feet of swiftly moving water.

Tied to the other eyelet was a 7-foot, 100- to 130-pound monofilament leader with a 1- to 1½-ounce bucktail on the end. The lengthy leader imparts minimal action to the bucktail jig, just enough that it flutters enticingly above bottom structure during the drift. The stiffness of the heavy 100-pound leader causes fewer tangles and results in fewer breakoffs, helping bring more fish to the boat.

A trailer is an essential addition to a bucktail jig on the Orient Rig and anywhere else they’re fished. The slow undulation of a pork rind or soft-plastic trailer complements the tantalizing pulsing of the bucktail hair. A scented trailer further adds to the jig’s appeal, and creates a larger, bulkier profile that helps bass see the offering in The Race’s deep, fast currents.

Visibility is low in these deep rips, so striped bass primarily use their lateral line rather than vision to effectively hunt. Even so, we opted for bright-colored white and chartreuse jigs to help the bass find our baits.

Orient Rig Trailers

When it comes to bucktail trailers for the Orient Rig, Captain Rich Jensen says the action is paramount. He favored Uncle Josh Pork Rinds until 2015, when they were discontinued. After that, he switched to durable synthetic strips. Uncle Josh brought back the pork-rind trailers in 2022, but Jensen still uses the synthetic ones; however, when the fishing is especially difficult, he switches to fluke ribbons or strips of squid to get bites.

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Captain Bruce’s Otter Tails

Originally designed as a seaworm replacement on the back of a tube and worm rig, Otter Tail trailers are scented, durable, and add action, color, and bulk to jigs.

Uncle Josh Pork Rind

Made of pork skin that must be removed from the hook and stored in brine-filled jars between trips, Uncle Josh “Sea Strips” were re-released in 2022 with 7-inch forked-tail and 5-inch straight-tail trailers

SPRO Eel-Tail Trailers

Available in single or split-tail styles in a number of vibrant colors including white, pink and green, these soft-plastic trailers are designed to enhance bucktail jigs with more scent and action.

Fat Cow Fishing Jig Strips

The synthetic material used to make Fat Cow Fishing Jig Strips is much more durable than traditional soft plastics and doesn’t dry out like pork rinds. These strips come in a wide array of colors and a number of styles and sizes from 3 to 7 inches.

Cut Bait

Squid pennants and fluke ribbons have good scent, fair durability, and an excellent undulating action. They can make the difference when the bite is tough

Fishing the Orient Rig

Like a drill sergeant, Rick paced around the deck as he sternly directed us in the proper technique for fishing the rig while the captain set us up for the first drift.

The technique is simple but requires concentration from the angler to avoid hitting snags as we drifted over hard bottom structure. On the incoming tide, we set up to move northwest into the rip, beginning in about 150 feet of water and drifting up the slope to near 50-foot depths that plateau Race Reef. The instruction given was to drop the rig to the bottom and upon contact, make five cranks to keep the sinker from dragging up the sloped bottom and losing an entire rig.

Five cranks was the general rule, but the number of turns on the reel handle is prone to change depending on the drift speed and the slope. It may feel unnatural, especially to bottom fishermen, but the sinker should not be dragging or touching bottom. Keeping it just above the sea floor eliminates the likelihood of the sinker catching rocks or wedging into a snag.

Enter the bucktail jig, which is now gliding over the bottom on the 7-foot leader to which it is tied. A 1-ounce bucktail could not maintain this depth on its own; it is the 10- to 12-ounce weight that allows it to remain in the strike zone. As the weight drifts up the slope, the bucktail trails behind, gliding just over the bottom. However, the bucktail may snag as well if anglers do not adhere to the mate’s suggested crank rule. Once the sinker begins to drag again, make five more cranks of the reel, and then wait. Repeat the process until the unmistakable thud causes the line to go taut, then set the hook and reel like hell.

The next goal is to keep the hooked striper from finding bottom, where it will use the rocky structure from which it came to free itself. With soft rod blanks designed to handle heavy sinkers and heavier fish, there is little backbone to muscle the stripers away from boulders, leaving the bulk of the work to the reel, line, and angler’s might to overpower the fish and successfully land it.

I stood next to my co-worker, Anthony DeiCicchi, with my camera in hand as he prepared to send 10 ounces of lead plummeting through the aqua-green depths. Once it reached bottom, he focused intently on keeping the sinker from dragging, and in short order, he battled a brawny bluefish to the surface. He posed for a quick picture with the blue, and the fish reciprocated by hurling a half-digested squid across the bow with a vicious, well-timed headshake. A couple of drops later, striped bass joined the party. At first, most were just under slot size, but with each drift, our crew began hooking larger fish.

I cranked and waited, then on the last few cranks of the drift, I received an unflinching thump from below. (That feeling sends adrenaline coursing through my veins every time.) I reared backward and up with the rod to ensure a hookset, and the battle ensued. It wasn’t a long one, but it quickly became evident why bass favor this environment. Several brief runs in different directions from my fish indicated it was darting toward structure to break me off. The pressure was on, and with the current on its side, this bass served me one last dive and a side of headshakes before it came to the surface. The 30-inch fish put into perspective what a trophy striper could do in such current. I decided to make one more drop before getting back behind the lens to capture the rest of the action.

Again, toward the end of the drift I got whacked. It’s a fishing cliché, but when I swung the rod upward to set the hook, I was certain I had snagged bottom. Line was peeling off my reel as Rick rushed over to investigate. He snatched the rod away from me to keep it from breaking. After trying to free it himself, he handed the rod back to me, wide-eyed, and stammered, “You’ve got a huge fish on. Reel!” I grabbed the doubled-over rod as he hurried off to get the net.

The mammoth striped bass that had inhaled my jig dove directly beneath the boat. I leaned over the rail with my rod tip now pointed 90 degrees downward as drag ripped out in spurts with such force that I could almost feel heat radiate from the gears. The furious current of “The Race” aided the flight of this large fish. We cruised west toward the top of the submerged plateau as the incoming tide flooded the mouth of the Long Island Sound. All I could think of was keeping my line away from the prop and the fish away from the rocks.

Even without eyes on it, there was no mistaking that this fish was bigger than any striper I had hooked in my lifetime. I could almost picture its broad, bullish head and hulking shoulders digging through the vast blue-green water column. Negating my efforts after a solid minute or two, the fish took a final plunge beneath the boat, this time heading in the opposite direction.

A split-second later, a decisive pop, followed by slack line, signified that I had lost the battle. A moment of utter disbelief ensued as I deflated from the loss of a sure trophy, but I quickly deflected any disappointment with the excuse I still tell myself today: “Some fish aren’t meant to be caught.”

Every now and then, you probably hear a story at your local tackle shop about a guy who hooked a fish that he just couldn’t stop. This time around, it was me. On that day I experienced a small dose of the Orient Rig’s capability to hook giant stripers. Although I’ll be haunted by that fish for life, I fully grasped the allure of striped bass fishing with this unique rig.

We continued with our drifts, but even in calm seas, we bobbed around in swells that were a product of the changing gradient beneath us. Trying to shake the empty feeling that had enveloped me, I passed off the stick to Anthony, who promptly dropped the rig as we reset for the next drift. After a few quick swings and misses, Anthony found a few more slot stripers that were promptly released after they fought from 100 feet of water in a kicking current.

Then, as we approached the inevitable “Lines up, guys,” signaling our hour-long return trip to the dock, Anthony hooked a beautiful striper using a SPRO Power bucktail tipped with a SPRO 4-inch single-tail eel trailer and brought it aboard for a quick photo. It was the nicest fish either of us had landed all day, and from the other anglers’ smiles, it was clear that they had also enjoyed the Orient Rig’s productivity.

I smiled, but for a different reason. I knew our boat had received just a taste of the bite that occurs around Orient on an annual basis, and although I experienced the wrath of a fish that will linger in my memory as the classic “one that got away,” I took comfort in having successfully fished The Orient Rig. I look forward to trying it in other striper waters from Cape Ann to Cape May.

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