The Winchester Model 1866, also known as the “Yellowboy,” was the first rifle to bear the Winchester name. Introduced in the immediate aftermath of the Civil War, the Yellowboy rifle and carbine were popular guns in their time and helped establish the Winchester Repeating Arms Company as one of the preeminent gun manufacturers of the late 19th century.

A Winchester 1866 Yellowboy rifle for sale now!

The Yellowboy was the original cowboy rifle, making its way Westward along with hundreds of thousands of settlers who followed the transcontinental railroad to seek their fortune on the frontier. With approximately 170,100 Winchester Model 1866 rifles, carbines, and muskets manufactured in total, the Yellowboy became the first lever action rifle and carbine design to see widespread use in every corner of the United States and beyond.

Famed Westerner Buffalo Bill Cody presented this classic Winchester 1866 Yellowboy to a man known as "Panther Bill."

Why is it called the Yellowboy Rifle?

The Winchester 66 was nicknamed the “Yellowboy” because of its distinctive gunmetal frame, forend cap, sideplates, and buttplate. Gunmetal is a strong bronze alloy composed of copper, tin, zinc, and sometimes a small amount of lead. Also known as “red brass,” gunmetal was rust-resistant and easy to machine.

The unique yellow tint of the gunmetal alloy gave Winchester’s first lever action rifle its distinct look and "Yellowboy" nickname.

The Yellowboy rifle’s gunmetal receiver not only aesthetically set it apart from its iron-framed competitors, but the material was also easier to work with than iron and provided improved corrosion resistance. The latter trait made the Yellowboy more durable in the harsh environments of the American West, where the nickname became the most prevalent.

A historic Volcanic Arms Co. carbine. The gun's receiver is composed of gunmetal, like its Henry and Winchester 66 successors.

The word "yellowboy" or "yellow-boy" is an archaic British expression for gold coins that can be found in writings throughout the 18th and 19th centuries. Given the yellow/bronze color of gunmetal on a glistening new Winchester Model 1866, it's no stretch to see why the yellowboy term was adopted for the rifle on the American frontier.

“I wish both their necks were broke, though the two cost me forty good yellow-boys.” - The Adventures of Peregrine Pickle by Tobias Smollett, 1751.

A Winchester Model 1866 Yellowboy saddle ring carbine manufactured in 1869 and later converted to .44-40 WCF centerfire.

The Winchester Model 1866 did not receive its official name in company catalogs until 1873, when the introduction of its famous successor required the two rifles to be differentiated. Before this, the Winchester Model 1866 was commonly referred to as the “Improved Henry,” “Winchester Repeating Rifle,” or the “Sixteen Shooter.” The later name was a misnomer and a carryover from the Yellowboy’s Henry rifle forerunner, which held a fifteen-round magazine capacity with an additional round in the chamber.

One of the most recognized Winchester 1866 Yellowboy rifles, the Nimschke "Bank Note" Winchester.

The Winchester Model 1866: Birth of the Yellowboy Rifle

In 1866, the New Haven Arms Company reorganized into Winchester Repeating Arms. Oliver Winchester’s factory superintendent, Nelson King, built off of the success of the Henry rifle, one of the few repeating longarms of the Civil War. This “Improved Henry” design incorporated the same double toggle link action but included a more efficient cartridge loading system with a spring-steel loading gate on the right side of the receiver, a fully enclosed magazine tube, and a wooden forearm under the barrel.

An Exhibition Grade Gustave Young panel scene master factory engraved, gold plated Winchester Model 1866 Yellowboy rifle.

The Yellowboy’s loading gate, also known as “King’s gate,” sped up the loading and reloading process, the closed magazine tube offered more protection from the elements, and the wooden forearm allowed for easier handling and shielded the shooter’s supporting hand from a hot barrel.

A Henry rifle (top) compared to a First Model Winchester 1866 "Flatside" rifle (bottom.)

Nelson King’s patent was issued on May 22, 1866. Shortly after, the Winchester board of directors authorized the manufacture of 5,000 rifles and carbines. Early serial records have not been preserved, but other company records during the period have noted that the "first two carbines of the new model" were sold on August 31, 1867, for $34 each. Early sales were promising, and the board authorized the production of another 10,000 Yellowboy rifles, muskets, and carbines on February 18, 1868.

Two Winchester 1866 repeaters. (Top) A Winchester Model 1866 musket with bayonet. (Bottom) A Winchester Model 1866 saddle ring carbine.

“It is of the same caliber and length of barrel as the Henry Rifle, and carries two charges more in the magazine,” Winchester declared in their original ad campaign. “It is lighter and more simple in its construction, less liable to get out of order, and is in every respect a better and more perfect weapon.”

An exceptional early production Winchester Model 1866 Yellowboy carbine with a Henry Patent barrel address.

Winchester Yellowboy Rifle Variations

The Yellowboy was offered in three different styles: rifle, carbine, and musket. In 1870, the Winchester catalog advertised the rifle for $50.00, the musket for $45.00, and the carbine for $40.00. Ammunition was offered at the price of $20.00 per 1,000 cartridges. Typical barrel lengths for the Winchester Yellowboy ranged from 20 inches for the carbine variant, 24 inches for the rifle, and 27 inches for the musket.

Two Winchester Yellowboys, a rifle (top) and a carbine (bottom.)

Even with their reduced capacity (13 rounds instead of 17) carbine versions of the Yellowboy were the runaway favorite in the United States. Winchester took inspiration from military carbines by including a ring and a staple fastened to the left side of the receiver near the hammer screw. This allowed the carbine to be secured to the saddle, earning it the nickname “saddle ring carbine.”

Documented Winchester Model 1866 carbine with a scarce nickel-plated finish and factory letter.

There are four different models of the Winchester Yellowboy, and you can read about those differences in detail in the article linked here. The standard configuration for the Winchester Model 1866 rifle, for example, is a 24 inch octagon barrel, crescent buttplate, and a full-length magazine, though this changed frequently throughout their production life. By the third model, Winchester had worked out many of the early design changes, so in addition to their dramatic increase in production, they also began to produce more custom pieces and stunning exhibition works.

A gold gilt, deluxe, factory panel scene engraved Winchester Model 1866 Yellowboy rifle chambered in the .44 Henry centerfire cartridge.

The vast majority of 1866 rifles and carbines were produced in .44 Henry Rimfire caliber only, a round with a 28 grain powder charge and a soft copper casing. A small number of mostly late-production rifles and carbines were converted to use a centerfire cartridge through the addition of a third firing pin protrusion at the center of the bolt face to supplement the two rimfire protrusions on the circumference. These conversions used the .44 Henry centerfire cartridges and not the .44-40 WCF developed for the Winchester Model 1873.

Two boxes of US Cartridge Co. .44 Henry Flat cartridges marked 'Von Lengerke & Antonie'.

“For Indian, Bear, or Buffalo hunting, it is unrivaled,” an early Winchester ad proclaimed. “And as a war weapon is as much superior to the Prussian Needle Gun, or any single Breech Loader, as they are to the old muzzle loading arms.”

The Winchester Yellowboy Rifle Makes an Impression

“The Winchester repeating rifle is lighter than the Henry rifle, weighing only nine and a half pounds, and can be fired eighteen times in nine seconds,” wrote the Louisville Courier Journal in an October 1867 review of the Yellowboy.

The Los Angeles Daily News had similar praise for the new Winchester in a June 1869 article on the gun. “All military companies should examine their new Infantry Rifled Musket with bayonet, which is said to be the most perfect and beautiful military arm ever produced.”

A rare L.D. Nimschke signed, engraged, gold finished Winchester Model 1866 lever action saddle ring carbine sold for $51,750 in RIAC’s September 2021 Premier Auction.

The Winchester Yellowboy quickly found favor around the country, including taking center stage in President Grant's reconstruction efforts in the recently defeated Confederate states.

In 1871, Rep. Ellis H. Roberts of New York, lamenting the frequency of KKK violence, referred to Winchester Model 1866 rifles and carbines serving as tools of intimidation for the southern militias. “Their weapons are often new and of improved patterns; and however poor may be the individual member he never lacks for arms or ammunition.”

An exceptional Winchester Model 1866 rifle with the 'Henry's Patent' barrel legend.

In March of 1869, the South Carolina Senate passed the “Winchester Rifle Resolution,” authorizing the governor to purchase 2,000 “Rifles of the most improved pattern” to arm the state's police force to combat racial violence and voter suppression. The resolution was postponed, but South Carolina and other southern state governments continued to acquire hundreds of Yellowboy rifles and carbines to aid law enforcement.

In 1871, South Carolina Governor R. K. Scott stirred controversy around the country with his “Winchester Rifle Speech,” where he suggested the best way to answer violence at the polls was to buy as many Winchesters as possible and one hundred rounds for each man willing to fight for fair elections. “I tell you,” the governor declared, “the Winchester rifle is the best law that you can have.”

This nickel-plated Winchester 1866 with its beautiful factory engraving was owned by Thomas Alexander Mellon Jr. the first son of Honorable Thomas Alexander Mellon who founded T. Mellon & Sons Bank and whose family amassed immense wealth.

The Winchester Yellowboy Overseas

In the fall of 1866, Oliver Winchester entered the Winchester Model 1866 into a Swiss trial at Aarau. A British trial at Wollwhich followed in 1868 with an experimental Winchester Model 1866 Musket. Both militaries were impressed, but backed out for financial reasons. Winchester found more success in Japan and France, shipping 5,000 Yellowboys to the Japanese in 1867 and 6,000 to the French during the Franco-Prussian War in 1870.

From top to bottom, the Winchester Model 1866 musket, the Winchester Model 1866 rifle, and the Winchester Model 1866 carbine.

The Winchester Yellowboy had another chance to shine as a military weapon when the Ottoman Empire ordered 5,000 carbines and 45,000 muskets in 1870 and 1871. During the Russo-Turkish War of 1877, Turkey delayed the superior Russian-Romanian force by using M1872 Peabody-Martini rifles at a distance, then switching to Winchesters at close range. The Yellowboy inflicted devastating casualties, showing the world the effectiveness of repeating military arms on a mass scale.

A historic Yellowboy rifle manufactured in 1867 and engraved to Peruvian military officer and politician Justiniano Borgono.

The Yellowboy was purchased throughout Central and South America as well, becoming an especially popular firearm of presidents, military leaders, and the wealthy elite.

This solid silver Winchester Model 1866 rifle, commissioned by President Jose Balta of Peru for presentation to President Mariano Melgarejo of Bolivia, sold for $977,500 in RIAC's December 2021 Premier Auction.

The Yellowboy Goes West

Repeating longarms like the Henry rifle and Spencer carbine had ceased to be novelties in the American West by the late 1860s, and the Winchester Yellowboy was quickly embraced as well. Gaining favor for its reliability, simplicity, impressive capacity, and rate of fire, the Winchester 1866 rifle and carbine became a favorite choice for hunting and self-defense, riding in the scabbards of many cowboys, lawmen, settlers, and outlaws of the era.

The Yellowboy and the Peacemaker, two classic guns of the Wild West.

Major John Wesley Powell, for instance, relied on Winchester Yellowboy carbines for game and security during his Colorado River expeditions in 1868 and 1871. Frederick Samuel Dellenbaugh, a topographer during the 1871-1872 expedition, noted that “Most of the rifles were Winchesters.”

A Winchester 1866 Yellowboy saddle ring carbine, dating to 1870.

In 1867, Red Cloud and Crazy Horse suffered a catastrophic defeat near Fort Phil Kearny, Wyoming in what would become known as the Wagon Box Fight. Two of the defenders toted Henry rifles and reportedly unleashed over 100 rounds of .44 Henry during the battle, helping repel the attack. The Native Americans learned from this defeat and took every opportunity to acquire “many shot” rifles as well, including the Winchester Yellowboy.

This extraordinary exhibition grade Winchester Model 1866 rifle was manufactured in 1872 and features 10 exquisite North American game scenes.

During the height of the Indian Wars, including the Battle of Little Bighorn, the Yellowboy rifle and carbine was far more common than its Winchester Model 1873 successor, outnumbering the '73's presence in America several times over in 1876. Major Marcus Albert Reno, who commanded three companies at the Little Bighorn, observed, “The Indians had Winchester rifles and the column made a large target for them and they were pumping bullets into it.”

A Winchester Model 1866 Yellowboy rifle, manufactured 1869 and later converted to centerfire.

Legacy of the Yellowboy

The Yellowboy rifle not only established Winchester Repeating Arms as a global brand but helped transform the company into a finely oiled machine that could push the boundaries of lever action rifle design. The Yellowboy’s successors, the steel-framed Model 1873 and Model 1876, were offered to the public in a bevy of new calibers and special order options. While the Winchester '73 is often dubbed the gun that won the West, the Yellowboy rifle helped set the stage for every lever action Winchester to follow.

This L.D. Nimschke exhibition engraved and relief carved Winchester Model 1866 saddle ring carbine, documented to Mexican President Porfirio Diaz, sold at RIAC in Dec 2020 for $345,000.

Though the Winchester Model 1866 was discontinued in 1898, the spirit of the Yellowboy rides on thanks to Uberti, Henry, and Winchester Repeating Arms (through Miroku of Japan.) These contemporary representations of the classic lever action are chambered in modern cartridges and are readily attainable for cowboy action competitors, hunters, and shooters today.

A deluxe, factory engraved and gold plated Winchester Second Model 1866 rifle with a Henry Patent marked barrel.

The Yellowboy Rifle in Popular Culture

As the original cowboy rifle, the Winchester Yellowboy has been featured in numerous novels, films, and television series depicting the Old West. In some cases, such as 'The Good, the Bad, and the Ugly' and 'True Grit,' the Yellowboy served as a stand-in for the Henry rifle. More recent prominent appearances include 'Back to the Future Part III,' 'Appaloosa,' 'Open Range,' and Paramount's 'Yellowstone' prequel series, '1883.'

In Taylor Sheridan's 1883 series, a Yellowstone prequel, Pinkerton Agent Thomas (LaMonica Garrett) carries a Yellowboy rifle that appears to be a centerfire conversion.

Yellowboy Rifle for Sale

As one of the archetypical Old West guns, the Winchester Yellowboy remains popular today with arms collectors, fans of the Western genre, and anyone interested in antique lever action rifles. While buying a reproduction can quench some of that desire for shooters, there’s nothing like owning an original Yellowboy or one of its lever action heirs, and some of the finest and most valuable antique Winchesters can be found for sale at Rock Island Auction Company.

Manufactured in 1869, this Winchester Model 1866 is beautifully engraved, with attractive floral scrollwork on a punch dot background displayed on the forend cap, with the left side plate engraved with a monogram and the lower tang featuring the initials "LDN" for Louis D. Nimschke.

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(Top) A documented Winchester Model 1876 rifle and a Winchester Model 1866 Yellowboy rifle.

Sources:

McDowell, R. Bruce. Evolution of the Winchester. Tacoma, WA: Armory Publications, 1985. Print.

Madis, George. The Winchester Book. Brownsboro, TX: Art and Reference House, 1985. Print.

Parsons, J. E. The First Winchester: The Story of the 1866 Repeating Rifle. New York: Morrow, 1955. Print.

Trevelyan, Laura. The Winchester: The Gun That Built an American Dynasty. New Haven: Yale UP, 2016. Print.

One of the most recognized Winchester 1866 Yellowboy rifles, the Nimschke "Bank Note" Winchester.