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Vintage Photos

20 Photos Of Sheriffs From The 20th Century

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A man in a wide-brimmed hat reclines on a wooden chair, balancing on two legs on a sidewalk. He leans against a stone building beside a quiet, empty street lined with trees and power poles.

Some of these images capture moments of calm and routine, while others freeze tensions in motion. Together, they tell a story of resilience and the evolving role of local law enforcement in a century that reshaped the nation. Here are 20 photos of sheriffs from the 20th century.

1. The first female sheriffs in Indiana, late 1940s

Two women in uniform and hats point pistols forward at a target while a uniformed man stands nearby, watching. The scene appears to be an outdoor shooting range, with a building and parked cars in the background.
userdeleted/via reddit.com

2. Alice Chandler, Orange County’s Sheriff in 1950

A woman in a sheriff’s badge, jeans, boots, and holster sits on a fence with one knee raised, outdoors in a rugged, hilly landscape.
pubwithnobeer/via reddit.com

3. Sheriff Chester Davis and his deputies with a moonshiner in handcuffs, Roane County, Tennessee, 1940

Five men in hats stand in front of a vintage car with several large glass jugs on the ground. The scene appears to be from the early 20th century, possibly during Prohibition. Trees and another car are in the background.
quick_presentation11/via reddit.com

4. Farmers “arrest” their sheriff for trying to evict a widow from her farm, 1952

Three men in hats and overalls tend to someone lying on the ground near a sign that reads, “This is exempt property from seizure. This is a widow’s homestead.” The mood appears tense and somber.
csa1935/via reddit.com

5. “My great-grandfather, sheriff and horse trainer, 1930s”

Black-and-white photo of a man with a beard wearing a hat, vest, and long-sleeved shirt, sitting upright on a saddled horse in a grassy outdoor setting with trees in the background.
powerful-knee3150/via reddit.com

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6. The sheriff of McAlerster, Oklahoma, sitting in front of the jail, 1936

A man in a hat leans back in a wooden chair on a sidewalk beside a stone building, balancing on the back legs with one foot off the ground. Power lines and trees are visible along the empty street.
gaget/via reddit.com

7. Ed Martin, Sheriff of Fergus County, grabbing a drink with his deputy, Montana, 1915

Sepia photo of an old-fashioned bar with a long wooden counter. Four men in early 1900s attire stand behind and in front of the bar. Bottles, a mirror, and mounted animal heads decorate the background.
userdeleted/via reddit.com

8. The sheriff of King and Stonewall County, Texas, 1906

A man with a mustache wearing a dark suit, vest, tie, and wide-brimmed hat stands beside an ornate, decorative chair in a vintage sepia-toned studio portrait.
oda_nicullah/via reddit.com

9. Sheriff Bartley Brown of East LA inspects Alex Rodriguez, 1943

A police officer in uniform lightly holds a man's neck while the man, wearing a striped shirt and oversized suit, stands with hands in pockets, looking serious. They are indoors beside industrial equipment.
grandlewis/via reddit.com

10. Famous boxer Jack Johnson surrendering to Sheriff Billy Silver, 1920

A group of men in early 20th-century attire gather outdoors, with two men in the center shaking hands near a turnstile gate. Several wear suits and hats, and brick buildings are visible in the background.
its_happening_again/via reddit.com

11. The sheriff of Santa Maria, California, and his deputies

Three men in suits and hats stand next to an old car. The middle man is older with a mustache and vest; the other two are younger. They pose in front of a building with large windows. The photo is black and white.
ventanaman/via reddit.com

12. Bank robber John Dillinger was handcuffed to Sheriff R.M. Pierce during his hearing, 1930s

Three men in suits sit closely together at a table in a dimly lit courtroom, while an audience of men in suits watches from the background. The mood appears tense and serious.
reporter_at_large/via reddit.com

13. Sheriff Willie of the Palm Beach County Sheriff’s office, 1977

Two men with guns, one in a SWAT vest aiming through a broken door window and another crouching behind a car, are positioned outside a brick building with a sign reading "Frances II.
rodigax/via reddit.com

14. A sheriff in Eureka, Colorado, walking with his deputies, 1903

Four men walk down a wide, dirt road in a small, old Western town with wooden buildings on both sides; mountains and green forests rise in the background under a blue sky with clouds. A child stands in the foreground.
routine_ask3374/via reddit.com

15. Sheriffs from St. Petersburg, Florida, standing by their new patrol cars, 1950s

A group of classic police cars are arranged in a star shape on a street, with officers standing beside them and one man in a suit at the center. Palm trees line the road.
mydoggold/via reddit.com

16. Sheriffs from Nashville examining the moonshine they confiscated, 1950s

Three police officers in uniform sit behind a box labeled "Pepsi Fountain Syrup" containing large glass jugs, in what appears to be a storage or evidence room. The scene is in black and white.
axlcobainvedder/via reddit.com

17. Sheriff Jim of Los Angeles holding a puppy, 1905

A man wearing a wide-brimmed hat and rolled-up sleeves smiles while holding a small dog in his arms. The photo is black and white, with a blurred background and a visible belt buckle on the man.
userdeleted/via reddit.com

18. The Calabasas Sheriff’s Posse, 1938

A black-and-white photo shows a long line of men standing outdoors in hats and suits, with a few individuals on horseback to the left. Tall trees fill the background under a clear sky.
malibuhuladuck/via reddit.com

19. Sheriff Lillian Holley and Prosecutor Robert Estill posing with John Dillinger after his arrival at Lake County Jail, 1934

A group of men in suits and hats stand together, with one woman in front wearing a dark dress and light blouse. The group appears to be posing indoors, with some people looking at each other and others at the camera.
brianoblivion1/via reddit.com

20. Rev. Thomas Gilmore, known as “The Sheriff Without a Gun,” 1965

A man wearing a cowboy hat and denim shirt smiles while sitting on a wooden fence, holding a small box labeled "Flower T. Oakes." The background is blurred and outdoors.
userdeleted/via reddit.com

Want to see more vintage content from the 20th century?

Check out 20 Colorized Photos from the First Decade of the 20th Century (1900-1910), or take a look at 15 Motorcycle Clubs That Were Born In The 20th Century. Finally, if you want to see why 20th-century games were grittier, take a look at 15 Vintage Sports Photos That Prove Why 20th Century Games Were Grittier.

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Meet the Writer


Patrick Nichols

Patrick is a writer based in upstate New York, where he grew up and still calls home. Over the past year, he’s been diving deep into storytelling, especially tales rooted in history, the Wild West, lost treasures, and ancient artifacts. He’s also drawn to unsolved mysteries and whatever the internet can’t stop talking about.

Whether it’s a centuries-old legend or a bizarre internet rabbit hole, Patrick is always chasing the threads of a compelling story. When he’s not chasing stories, Pat’s probably hiking mountain trails with his dog, exploring new corners of the U.S., or doom-scrolling between hangouts with friends and family. He finds inspiration in nature, forgotten places, and random conversations—anything that sparks curiosity. Whether it’s city streets or backcountry paths, Patrick’s always on the lookout for the next great story.



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