Texaco – Madams and Mayhem at the Dew Drop Inn on Beaver Rim – Ed and ‘Big Anne’ Wynn

(Note: Special thanks to Hailey Redden at the Pioneer Museum for research on Ed and Anne Wynn.)

A string of seemingly unrelated events can bring about more profound change than the most detailed plan of action ever can. Newspapers, a highway, a service station, a restaurant, a hotel, and a rekindled romance created just such a string atop the cold, windswept ridge of Beaver Hill in southeast Fremont County in the 1920s.

Edward and Anne Wynn found a home atop Beaver Rim, but it wasn’t until much later in their lives that they came together. As J.R.R. Tolkien wrote in ‘The Fellowship of the Ring,’ “not all those who wander are lost.” But wander, Anne and Ed did in abundance.

The road to Lander from the Union Pacific Depot in Rawlins was surveyed by the United States Army Corps of Engineers in 1878. It became known as the Rawlins to Ft. Washakie line, home to stagecoaches and freight wagons for the next 28 years until the rival Chicago North Western railroad ended at least the freight service since its western terminus was in Lander.

Their story begins with Ed’s father, Isaac.

The Wynn Family at the Wind River Mountaineer Office 1898 – Pioneer Museum

Lander Clipper – May 28, 1897 – Page One

“Isaac C. Wynn was born in Scioto County, Ohio, October 20, 1830. He enlisted in the United States Army at the beginning of the war, served eighteen months as a private, when he was promoted to the rank of Second Lieutenant, which rank he held until the close of the war, being mustered out with the rank of First Lieutenant. Returning to his home in Ohio he held appointive positions under the government for eleven years, which he resigned in 1880, and removed to Teller, Colorado, where he remained for three years.
He came to Lander in July, 1884, and established the Mountaineer, January 1, 1885, which he sold in May, 1887, and started The Clipper in September of the same year. Disposing of this paper in September 1893, he removed to Los Angeles, California, where he remained until the summer of 1895, when he returned to Lander and bought the Mountaineer, which he has personally edited up to the day of his death.
Mr. Wynn was one of the pioneer newspaper men of Wyoming, and long experience and a peculiar aptitude for the business made him one of the very best in the state. He was a man of patriotism and firmness. His appointment as postmaster at Lander during the Harrison administration, finished a long public career, that was singularly well rounded, and ended with the highest honor. He had always been a Republican up to one year ago, when the cause of the people, as he looked at it, appealed to him in the free coinage issue, of which he became an ardent, honest and honored advocate. His personal character and honorable record entitle him to the high esteem with which he was regarded by his fellow citizens.
He leaves three children to mourn his loss, John W. Wynn, Boseman, Montana; Edward R. Wynn and Mrs. Cora V. Preston of this city.”

Just prior to his enlistment in the 56th Ohio Infantry, his son Edwin Ruthven was born on February 9, 1861. While he was on active duty, his daughter, Cora Viola, was born.

Edwin “Ed” enlisted at 16 in the Ohio National Guard but earned a living managing a store near Chillicothe, Ohio.

His father and Cora moved to Lander in 1884. Cora worked with Isaac at the Wind River Mountaineer.

Ed followed his father’s footsteps and became the editor of the Lexington Leader, in Lexington, Kansas, in 1886. In 1887, he moved west to the tiny town of Las Animas (Lost Souls), Colorado, where he worked as a writer for the Las Animas Bugle.

Courtroom sketch of Big Annie Young in 1900 – Oklahoma Historical Society

Ed and “Big Anne”

While working in Las Animas, he met Anne Cecile McLaughlin. Anne was born in 1863 in Illinois into a family of 18 children. Anne was a tall woman, over six feet. Anne left home at 17 for Colorado in 1880. She began working as a prostitute in mining camps around Leadville.

Anne’s commanding presence led her to become the madam of a brothel in Leadville.

Las Animas and Leadville are about 250 miles apart. It is speculated that Ed met Anne while working on a story about the mines in Leadville.

The couple was married in Rawlins, Wyoming, on August 5, 1887. Ed opened a newspaper, serving as publisher of the Arlington Leader in 1888, 30 miles north of Las Animas. Anne spent most of her time at the brothel in Leadville.

Times were changing in the Colorado Rockies. The wild days of the gold and silver rush were ending, and civilized society replaced the boisterous miners. There wasn’t a place for brothels like the one Anne ran.

Ed suggested they move to Lander, where he would work with his father and sister in the newspaper business. Anne didn’t like Lander and left Ed less than a year after they were married, returning to Chicago in 1888. She left Ed in Lander. In May 1892, Ed filed for divorce at the County Court in Lander.

Leadville had been good to her. Seven years running a brothel in that rough Colorado mining camp had taught Annie everything she needed to know about men, money, and survival. In 1889, when word spread of free land in Oklahoma Territory, Annie packed up and followed the rush.

“Big Anne” Bailey – Edmund, Oklahoma Sun – January 3, 1908

Taken from excerpts in the Oklahoma Daily Pointer, 1908

The Land Rush was chaos. Oklahoma City sprang up almost overnight. Annie claimed a plot between the First National Bank and a saloon, just across from the Santa Fe Railroad Depot. Within a week, she had a tent up and business underway.

The district that grew around her came to be called Hell’s Half-Acre, a place of whiskey, cards, and quick fortunes won and lost. Saloons lined the streets, gambling halls hummed through the night, and brothels did brisk business. Annie thrived there. Tall and weighing over 200 pounds, people started calling her “Big Annie.” The name stuck.

Annie then married a man named Young and became known around Oklahoma as “Big Annie Young.”

Annie formed a partnership with Martha “Big Zulu” Fleming, an African American madam. Together, they built influence as well as profit, backing local political efforts and making allies where it counted. It helped. Their operations sat just outside city limits, beyond the easy reach of the Oklahoma City police. For years, Annie managed to stay one step ahead of the law.

She never pretended to be anything other than what she was. When the 1900 census came around, Annie and her women listed their occupation plainly as prostitutes. Yet she moved through Oklahoma City with surprising ease, able to step into respectable shops and blend in among well-dressed women of higher society. Merchants welcomed her business. It was not her profession that stirred the most resentment. It was her success. Annie bought land, and a great deal of it. For some, that was harder to accept than anything that happened in her establishments.

Courtroom sketch of Big Anne Bailey, 1908 – Oklahoma Historical Society

In 1896, she was convicted of running a bawdy house and sentenced to a $500 fine or thirty days in jail. She paid, and business continued.

She divorced Young, and on June 4, 1903, Annie married Asher Bailey.

That same year, a young Dutch woman, Lucy Platt, claimed she had been drugged and raped after visiting Annie’s establishment. Witnesses said the women had entered willingly, accepted drinks, and gone upstairs. The men came downstairs calmly and left. George Garrison and John Harmon were charged with rape. Garrison served ten years. Annie was charged with contempt of court. Around town, whispers spread that the whole affair had been arranged.

The trial of Big Anne Bailey made sensational reading – Oklahoma City Pointer March 23, 1908

That same year, violence struck closer to home. Effie Fisher, who managed Annie’s most profitable house, was shot through her window and killed. Before her death, she had said that if anything happened to her, blame her former lover, Ed Filson. He was tried and acquitted.

In 1907, one of Annie’s houses burned to the ground in the night, killing four people.

Annie was arrested. Judge Peters, a porter, was charged with arson and murder. The case rested on the story of a former employee, Fannie Richards, who claimed she had killed a man, disposed of his body in the North Canadian River, and started the fire to hide the crime. The charges were dismissed.

The cost of staying free kept rising. Lawyers, fines, and constant scrutiny wore down Annie’s fortune. By then, she had amassed around $75,000, but much of it went toward keeping herself out of prison.

In 1909, Annie and Asher Bailey moved to Southern California. To the people of Oklahoma, that was the end of the story of “Big Anne.” It was just getting started.

Big Anne Bailey didn’t have much to say on the witness stand – Oklahoma City Pointer March 19, 1908

Back in Wyoming, Ed and Cora continued to help their father in the newspaper business. Isaac sold the Mountaineer in 1885 but started the Lander Clipper later that same year. In 1893, he sold the Clipper and moved to Los Angeles.

His life in California lasted just two years. In 1895, he purchased the Mountaineer and moved back to Lander.

Isaac Wynn died in 1897, leaving the Wind River Mountaineer to his son and daughter.

Cora had the same luck in marriage as her other brother did.

She married Douglas Preston, and the couple had a son, Donald. They were divorced, and she married John Wesley in Lander

Wind River Mountaineer – January 10, 1899

“The modesty of the publisher of the Mountaineer sometimes is exercised over its editor to such an extent that matter has to be condensed especially is this the case in making mention of her marriage last Sunday January 8th.

At eleven o’clock or thereabout carriages bearing occupants consisting of intimate friends of the bride and groom began to leave the city their destination being the home of Mr. and Mrs. J M Reid at which place the lives of John Wesley and Cora Preston were to be united in marriage by Rev O L Ramsey.
Invitations had been issued by the host and hostess to only the very most intimate friends prompted by the bride and groom and not with but very few exceptions did those invited fail to respond.
About twenty five persons assembled to witness the ritual which is termed the ring ceremony and is impressive to such a degree that tears freely flowed from many eyes while Rev Ramsey of the Lander M E church was pronouncing the pledge and vows in his own solemn way and in a manner that taught his audience to revere and respect him for all time to come.”

Cora Wesley divorce notice – Lander Clipper – April 8, 1904

Cora was the editor of the Mountaineer since her father’s death. She resigned in June 1899, and Ed took over the paper.

The marriage to Wesley was rocky from the beginning. He was rarely home and didn’t contribute to the family income. Cora had had enough.

Lander Clipper – November 21, 1902

“Mrs. Cora Wesley, accompanied by her two bright little children, left on the Casper stage Saturday morning for Chillicothe, Ohio, where she will spend at least a year visiting her mother and friends of her former home. Mrs. Wesley has gained a reputation throughout the state, by editing the Wind River Mountaineer, as a brilliant wielder of the quill and many regret her temporary retirement from newspaper life.”

On April 8, 1904, Cora divorced John Wesley for non-support, one of the few avenues open to women for divorcing their husbands at the time.

She married Karl DeForrest Graves and the couple had two daughters, Alberta Eliza Graves and Beatrice Graves, adopted by Karl. Cora had finally found peace with Graves, but tragedy soon struck again.

Beatrice Graves marker – Mountain View Cemetery

Wind River Mountaineer – January 5, 1906

In all Lander a month ago no one seemed farther away from the grim reaper than did pretty little Beatrice Graves. Bright-eyed, winsome and seemingly the picture of robust health she suddenly sickened and the ailment rapidly developed into that dread scourge, spinal meningitis, mild in form at first, so that for three weeks hope reigned high in the hearts of parents and friends. In spite of the loving care and skilled nursing and medical attendance the disease conquered and the evening before Christmas she wearily pushed away the new doll and murmuring brokenly, “Now I lay me… Now I lay me-down-to sleep” sank into the coma from which she never awakened on this earth.
The funeral services, of which a touching incident was the attendance in a body took of the primary department of the Lander schools, were held at the Methodist church, Thursday afternoon at two o’clock, and were conducted by Rev. P. N. Fredin after which the remains were buried in the I.O.O.F. cemetery.”

Our tender prattling baby-
Our precious pearl and pride,
Was kissed by the darksome angel-
She sickened, she dropped and died.

Like a beautiful ray of sunshine
That fades ere we sink to sleep-
Like a perfect pearl from the seashore
That is lost in the darkness deep,

She folded her hands and faded-
She sank away from our sight.
The snowflakes are lightly falling
On her little grave tonight.


Cora worked as editor of the Lander Republican after losing her daughter. Ed worked as the pressman. They left the Republican in 1908. Cora followed Karl to papers in Thermopolis and later Basin where he was editor of the Big Horn Pilot.

Ed Wynn was a man of many interests – Hudson Miner June 15, 1917

Ed became a rolling stone. He quit the newspaper business and began raising sheep in the Sweetwater Valley and South Pass, spending time at Split Rock, Rongis, Myersville, Lewiston, Miner’s Delight, Atlantic City, and South Pass City.

On July 12, 1920, he applied for a 160-acre homestead at Hailey, near the top of Beaver Hill. He added another 480 acres to his homestead on February 6, 1925. He was a friend and neighbor of Eli Signor, the man who founded Rongis and later purchased Hailey. Ed often stopped by Eli’s place at Hailey, admiring his orchard and talent in growing wheat, corn, and sugar beets along Beaver Creek.

Ed Wynn was a man of many talents, and his keen sense of economic opportunity was fueled by his many years and many connections made in journalism.

Automobiles were expanding at a nearly astronomical pace in 1920s America. The road from Rawlins to Lander was still just a steep, undeveloped, two-track wagon route. Traffic was increasing along the road, and the state of Wyoming finally noticed.

Wyoming State Journal July 18, 1924

The Wyoming Highway Department allocated funds to improve the roadway, calling it the Rocky Mountain Highway.

Ed’s homestead was adjacent to the new highway. In 1927, he moved his house and outbuildings next to the developing roadway. He made another, even bigger move at the end of 1927, remarrying Anna.

The Journal’s narrative of Anna’s past was worthy of a Washington D.C. politician’s public relations firm.

Wyoming State Journal – December 21, 1927

RE-UNITED AFTER SEPARATION OF 38 YEARS

“Cupid went on a vacation for thirty-eight long years when he married Miss Anna McLaughlin and Ed Wynn as the two separated soon after the wedding, she going to California and he, one of the pioneer printers of the county, remaining to work on the Fremont County Clipper assisting his father, I. C. Wynn, in the publication of that paper. Thirty years ago, she married an Oklahoma man who died a few years later leaving her with his five children, all of whom have grown to maturity, married and have homes of their own. This maternal obligation discharged, her thoughts returned to Lander and the happy days of youth and she began to wonder what had become of her girlhood sweetheart. Mr. Wynn learning of her inquiry extended urgent and cordial invitation for her to come to his ranch at Big Cottonwood Park near Hailey where after a few weeks of courtship they decided to be reunited in marriage. Hanford Mills rigged up a honeymoon special and brought the happy couple to town on Wednesday. The wedding took place at the Fremont Hotel with Judge C. R. Wells officiating. Arthur Vaughn and William Fisher were the witnesses.”

Gas pump at the Beaver Station behind the Dew Drop Inn 1930 – Pioneer Museum

The couple lived at the homestead on Beaver Hill. In 1928, the road began to take shape with gravel and shale added to the steep slope up what would become known as Beaver Rim.

Anna and Ed opened a store along the highway and installed gas pumps. The location was closer to Lander than Rawlins, but it was ideal for travelers working their way between the two towns on the improved, but still treacherous roads.

Ed contracted with Ben Laws in Riverton for fuel and became a Texaco dealer.

Credit goes to Anna for the final innovation at Beaver Hill, a combination restaurant and motel called the Dew Drop Inn.

A tintype of the Dew Drop Inn 1930 – Pioneer Museum

The name was a common one across the Great Lakes, the Midwest, and the Rocky Mountain region, but it was a hit.

Locals arrived for dinner still driving teams of horses and freight wagons. Truckers stopped for breakfast and lunch on the route from Riverton and Lander south to Rawlins and then onto Denver, and motorists relished the break from the highway.

Ed and Anna were happy at Beaver Station.

Ed suffered a stroke in July 1929, but recovered enough to continue operating the store, service station, and the Dew Drop Inn. Anna was a devoted wife, caring for Ed.

In 1935, with Ed’s condition deteriorating, they closed the business, sold the ranch and moved to Lander. Opposite his cabin, he buried a loyal sheepdog on a ridge where he could see the pile of rocks each morning. He wrote this poem in tribute to his canine friend.

“Silent pile upon the hill top,
Landmark of the wasteland all around;
Set midst silence most profound.

Guide for man and flock returning
O’er the hills at daylight’s end;
Man who has no other helper
Save his faithful shepherd friend.

Monument of patient labor,
Builded slowly, stone on stone,
But to while away the hours,
Hours he spent there all alone.

Who can tell what thought came o’er him,
As he toiled there alone?
Some past time he may have spent
With red placing of each stone.

Each stone may be a hope departed,
Or past that now lies buried deep,
While memories crowd upon him
In close array like flocks of sheep.

The pile of rocks may not be clean,
It may not be a work of art,
But it may be a sign of longing
In some poor shepherd’s aching heart.”

Ed suffered a cerebral hemorrhage and passed on February 21, 1936. Anna passed almost a year to the day on February 23, 1937.

The unlikely couple is buried side by side at Lander’s Mountain View Cemetery.

Born during the Civil War, meeting, then taking very divergent paths, the couple was meant to be with each other through eternity.

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