According to contributor 'Bunny' (George Opper), "Sailor Ann's" was a gay destination as "a cruising bar and pickup joint" until a 1958 remodel that made it "just another steakhouse".

Michail Takach wrote the following article on the bar/ restaurant for this website, which also ran on the OnMilwaukee.com website in February 2024.

(According to folklore, Wally Whetham bought many artifacts "at rock bottom auction prices" from the closed "Sailor Ann's" to furnish his new "Captain's Cabin" bar at 400 N. 2nd Street, a former "Gay 90s" saloon.)

Sailor Ann's celebrated the spirit of the Fifth Ward
Historic tavern served the Reed Street Yards for over 60 years

Milwaukee may be the "gathering of the waters," but for a century, Walker's Point was the gathering of Milwaukee's rivers and railroads. This convergence caused an explosion in industry, commerce, and hospitality and created a destination for young, single, starry-eyed workers from all over the world. Going wherever the work was, they lived chaotic, unpredictable, transient lives. Most were comfortable with the freedom of life on the "sail and rail"- at least, until they found their fortune, bride, and family.

Workers also lived, worked, and breathed an exclusively male existence: on the job, at the rooming house, in the workplace, even in men's-only taverns and restaurants. Life was shockingly segregated for unmarried people, creating an ever-simmering sexual pressure cooker in closed quarters.

Long before "gay bars," sailor bars could be found in every major American city.

Sailor bars were taverns located near the docks where marine workers gathered for meals, drinks, and mingling before, during and after working hours. These were the original dive bars- and they were extremely popular. These were often rough, disorderly, dangerous places in socially unacceptable neighborhoods where women and children were unsafe and unwelcome. For these reasons, morals were loose, drinks were strong, and laws didn't always apply.

Under this smoke screen of lawless vice, down-low men found community and companionship that couldn't exist outside this world.

"Men...who understood themselves as gay went there to meet sailors and dockworkers who may not have ever thought of themselves as gay, but were having sex with other men," explained author Hugh Ryan in a May 2022 NPR interview. "Nearby streets are less policed, less gentrified…(these were) places where sex work can happen, where bars that catered to men who were flaming and women who were masculine could appear, and be slightly safer….For all of these reasons, the docks became epicenters for early queer community."

Whether mainstream Milwaukee knew it or not, Sailor Ann's was one of these bars.

Who was Sailor Ann?

Anna Gravelyn (nee Gravelijn) was born in Grand Rapids, Michigan on September 14, 1876. Her parents, Cornelius and Johanna "Jennie" Gravelijn, descended from a long line of mariners in the Zeeland region of the Netherlands. Her husband, Michael E. Hands (1864-1920,) came from Ireland to make his fortunes in the teamster trade. By 1895, he'd forsaken all that to open his own saloon, the Calumet Liquor Company. Anna and Michael married in 1900. He was already a confirmed bachelor of 36; she was considered an old maid at 24 living with her mother. Although both came from large families, the couple never had any children.

It's unknown what brought Anna and "Hands" to turn-of-the-century Milwaukee, but they opened the Sail & Rail Hotel & Buffet at 222 W. Florida Street in late 1900. Their business, at the southern edge of the Reed Street Yards, was an immediate and lucrative success. The Sail & Rail became a popular rendezvous spot for Great Lakes captains, sailors and longshoremen, and matchbooks promised beer "only a cable throw from the Milwaukee and Menomonee Rivers." The bar was decorated with steamboat and windjammer pictures on one wall, and an ever-growing collection of railroad switch keys on the other. The revolving door of colorful characters was more fascinating than the food and grog menus. Newspapers spoke of "lusty seamen, brawny dock wallopers, roughneck railroad workers, and the occasional vagabond, all presided over by the Queen of the Marine District, Sailor Ann herself."

Anna spoke the coarse and colorful language of the workers, and they respected and admired her for holding her own against rough crowds. She played dice, drank whiskey, wore pants, chewed tobacco, smoked cigars, and shot guns for fun- things women were simply not supposed to do. She hadn't taken her husband's last name at marriage, and curiously, she was so popular in Milwaukee that her husband "Hands" starting using her surname.

"Every morning, the sailors would come in, Sailor Ann would give each of them one drink and 50 cent and send them down to the tug office at the foot of 2nd St. to find work," recollected the Milwaukee Journal. "Grannie Jennie sat in a rocking chair in the corner of the bar, but never turned down a poker bet, a shot, or a drink. A customer would invite her to have one on him, and Grannie would rock the chair back and forth fast enough to get on her feet and walk to the bar. Visitors will never forget her thick Dutch accent."

Ann's nephew, Gerritt Stell, would later deny the bar was a hangout for common, beer-drinking dock workers. However, newspaper accounts called Sailor Ann's a place for "whiskey-soaked, hairy-chested, tattooed sailors tending their battle wounds, with cargo hooks bulging from their hip pockets." Sailor Ann was known for her taste for Haig & Haig whiskey, then a premium brand, which she sold at loss leading prices.

"Jaunts With Jamie," a Milwaukee Journal column, reflected:

Dockside streets used to be roisterous and rowdy places. Back in those days, the river was still crowded with boats unloading tanbark, railroad ties, cedar posts, lumber, and coal. There were barges of brick and sand, high-stack tug-boats, and grizzled skippers who thought they owned the rivers. Small and large steamers docked at the grain elevators. Package boats were battling the huge car ferries. Every afternoon, the Columbus, a huge excursion vessel from Chicago known as the whaleback, dwarfed buildings along the Milwaukee River as it made its way to the Goodrich Docks. The Bloomer Girl and Cyclone made regular trips between Milwaukee and Michigan ports during fruit season.

Sailor Ann's was remembered for maintaining the beer towel tradition long after other saloons abandoned it- that is, a shared towel the keeper offered to wipe beer foam from a man's facial hair before he headed back to work. After all, if they lost their jobs, they wouldn't have money to spend at Sailor Ann's.

By 1915, the Fifth Ward had 211 licensed taverns within seven blocks- one for every 79 neighborhood residents and more than any other ward in the city- and Common Council reformers started to question the public health impact. Aggressive health inspections and licensing requirements followed.

"The breweries have a strangehold on the taverns, and the taverns have a strangehold on the workingman," wrote the Milwaukee Journal. "If Councilmen succeed at shuttering 150 saloons as planned, Milwaukee can expect riots on Reed Street."

Heavy pours in a dry town

Sailor Ann wasn't worried about the Common Council. By Prohibition, she was so well-connected that she was considered "untouchable."

While supposedly running a soft drink parlor, she unapologetically operated one of the city's most notorious speakeasies. Liquor flowed around the clock in defiance of curfews. Gambling started with bar dice, continued with a bookie operation in a secret adjoining room, and eventually grew into a full basement casino accessible through a secret trap door. After years on the up-and-up, the Sail & Rail was now regularly raided by Prohibition agents, Morals Squads, and even the IRS.

After her husband died in August 1920, Sailor Ann took in her employee, Anna Stackland, as a living companion. The women grew up together in Grand Rapids' Dutch community, so this may have seemed reasonable to bystanders at the time. Today, it seems like a convenient cover story. First of all, Stackland's husband was very much alive and even living on the property. And even stranger, Stackland was accused of embezzling over $2,000 ($72,000 in today's dollars) from Michael Hands four years earlier. Although the Milwaukee Sentinel published the accusations, Stackland was never charged, fired, or evicted from her residence at the Sail & Rail. Instead, she held the favored position of bar manager, a rare role for a woman in 1920, and lived with Sailor Ann for the next 14 years.

Milwaukee Journal columnist Larry Lawrence must have raised eyebrows with this 1924 article, which showcases both the sailor bar experience- and Sailor Ann's acceptance for what was happening there.

A sailor and a switchman stood together at the bar at the Sail & Rail. Ann, the proprietress and bartender, smiled a golden smile at the youths and greeted them by name. The boys talked together for a time, then left together to points unknown. An old man who had seen years of service on the lake carriers shook his head as the youths left the unique saloon, headquarters for the men who work on the boats and trains.

"There are some odd traditions about this old place, ain't there, Ann?" he asked. "Yep, there sure are," Ann answered, mopping the bar again, although it was perfectly clean and dry.

Whenever Dave is in town, you'll find him with Mike, and sooner or later they'll drift into the Sail & Rail. And so it goes. There are rows of switch keys above the bar, hundreds left by the men who shunt the cars back and forth in the yards and on the roads, completely covering the framework of the bar. Each one, one of these boys; each one, a connection made at Sailor Ann's.

George "Bunny" Opper, a long-time contributor to the Wisconsin LGBTQ History Project, described Ann as a "sweet, but tough old broad, who celebrated all kinds without ever speaking about herself, who was as well-versed in weaponry as she was in whiskey. She had a bayonet behind the bar- and she knew how to use it."

Gerritt Stell remembered:

"I got my start here in 1927 as the lookout man. When a customer stepped on the mat in front, a red light flashed. So, I'd go and look out the peephole. If we didn't know him, we'd just leave him standing there."

Reliable customers were recorded in a birthday book by their birth dates. If a fellow came to the door and claimed to be a former patron, Gerrit would ask him when he was born. If his name was entered under that date, the fellow got in, Otherwise, the peephole slammed shut and that was the end of it.

"Customers were lucky to get drugstore whiskey. I went out every day looking for it. I paid doctors $2.50 apiece for whiskey prescriptions- some of them were living on the two-fifties- and I gave the druggist an extra 50 cents to fill them. The stuff costs $5.50 to $6.00 a pint. We sold it for 50 cents a shot."

Later, the "birthday book" tradition was widely utilized by early gay bars to maintain the safety and privacy of their clientele.

Sailor Ann was almost untouchable. Almost. On January 7, 1931, her luck ran out.

"Surprise Raid is City's Biggest Retail Rum Offense," screamed the headlines. "Drys Mop Up 26 Downtown Saloons." Prohibition agents rushed the bar, arresting patrons, seizing liquor and gambling machines, and actually tackling Sailor Ann. The Sail & Rail was padlocked and its contents surrendered to the federal government.

"The 40-year-old mahogany bar, the traditional moosehead, the pretty pictures of nude women, the poster of Mayor David Rose, even the historic stein collection. All went into a huge van bound for the warehouse. They took everything but the barroom cat in one of the most spectacular raids in history.

It was a terrific governmental punch at Milwaukee night life… It left saloon keepers, bootleggers, and underworld characters so punch drunk that the headaches Wednesday morning will be on the other side of the bar."

After an earlier liquor charge in 1926, Sailor Ann was in big trouble now. Of course, the community sided with the tavern keeper over the law. The Milwaukee Journal reported that "three hours of testimony and cross examination, more resembling the script for a comic opera, enlivened district court yesterday. The Raid of Sailor Ann's supposedly began when agents heard the clink of money and the clatter of slot machines from an alleyway. So, naturally they barged in and floored Sailor Ann herself. When questioned, vice squad Officer Lester Bliffert claimed Sailor Ann fainted from seeing a strange customer. The gentle officer certainly does not know Sailor Ann."

In the end, Ann spent 30 days in jail. She later lamented, "so many arrests, but only one conviction." The joke was on the justice system. When she left jail, Ann recovered her tavern property and reopened the business as "Sailor Ann's" in 1933.

"It was never, let's go up to the Sail & Rail, but always, let's go up to Sailor Ann's," wrote the Milwaukee Journal. "The Queen of the Marine has taken back her crown."

The golden years

Having lost her husband in 1920, her mother in 1930, and her companion in 1934, Sailor Ann showed no signs of slowing down throughout the next decade. She promoted her nephew Gerritt Stell to general manager. She hired Paul "Frenchy" LaPointe to run the kitchen. After extraditing her niece-in-law Stella Stell from Los Angeles, after she'd stolen $1,200 in a 1926 scheme, Ann put her to work in the family business. Despite the shame of headlines like "Captured Elopers Planned Daring Break from Boredom," Sailor Ann and her nephew William forgave the runaway bride.

Sailor Ann made headline news in the 1930s when she hosted a visiting Arctic dog sled team. The fleet, including eight puppies born during their stay, became a rooftop tourist attraction at the bar for a week.

She continued to battle the Morals Squad, who seized her slot machines (1934 and 1936,) broke up her 26 dice game (1935,) demolished her roulette table (1936,) shut down her blackjack game (1937) and launched a violent raid of her basement casino (1940) which resulted in an "arrest on sight" warrant. Civil Judge A.J. Hedding repeatedly threw out the charges, citing illegal search and seizure violations. The city knew better.

Despite all this highly-publicized harassment, Sailor Ann's photo never appeared in the local papers. Rumor has it that she was highly superstitious about having her photo taken by strangers, and didn't allow reporters to take them. Extensive research has only revealed one photo of this remarkable woman, long before she became "Sailor Ann."

Sailor Ann died on June 1, 1944 after a six month illness. She was only 67 years old. Her nephew Gerritt kept the business going for another 14 years, despite gambling raids that continued until 1948. When his health began to decline, he brought his sons Thomas and Jerome Stell to run the aging venue.

Sailor Ann's last hurrah

As long on ambition as they were short on cash, the Stell nephews sought to reinvent Sailor Ann's for the next generation.

This was more of a necessity than an option. Commerce shifted from the rails and rivers to air travel after World War II. Milwaukee turned its back on the rusty old Reed Street Yards, an increasingly polluted Milwaukee River, and block after blocks of aging, abandoned pre-Civil War buildings. By the 1950s, the old Marine District had lost its purpose, its population, and its reputation.

Few people could even remember why it was ever called the Marine District, so newspapers and advertisers started using a new name for the neighborhood: Skid Row.

The Stell nephews saw an opportunity to cash in on nostalgia- and it worked. For the second time in 25 years, they remodeled the dining room, where top chefs offered aged charbroiled steaks, fresh venison, duck, pheasant, and racks of lamb, as well as two pound, $1 lobsters flown in "daily" from Cape Cod. They boasted the best New England clam chowder, supposedly from an old Pilgrim family recipe. They proudly installed Wisconsin's only oyster bar, which added a splash of sophistication to the old Fifth Ward. They brought the old barroom out of "dry dock" with renovations that made it "as seaworthy as the finest ocean liner." And they introduced a modern cocktail lounge that startled even Gerritt Stell, who famously commented, "Martinis? People who come to Sailor Ann's don't drink martinis!"

"Sailor Ann's still smacks of adventure with a capital N- N for Nautical," wrote columnist Jim Koconis in the Milwaukee Sentinel on October 7, 1953. "It took more courage than we thought to push open that old door. We were certain some bucko mate would bellow, 'well blow me down! There's a lubber if I ever saw one!' But the new Sailor Ann's has risen to a position of leadership among Milwaukee's fine dining."

The Stells installed a Captain's Table and launched a Friday night tradition of inviting visiting sea captains, ship agents, Coast Guard officers, and military men to dine together. They brought in organ music, bands, and even dancing. They marketed the bar as "just three 2s to the west" of the South 1st and 2nd street thoroughfares.

The new concept attracted a much higher-end clientele, including urban professionals and civic leaders who never would have visited the historic haunt. Sailor Ann's was no longer a workingman's whiskey hangout, but an upscale destination safe for bringing the wife and kids. In some ways, it had become a theme restaurant- anchored in a rugged and dangerous world that no longer existed.

The Milwaukee Sentinel wrote:

The "good old days" was always part of the Sailor Ann's experience.

The stories they used to tell! They made the Great Lakes avenues of adventure, which indeed they were back then. If only the walls of the old place could talk. And perhaps, if you have the heart to listen, you'll hear about epic battles with the elements. The famous schooner race from Buffalo to Milwaukee might come echoing off the walls, as it has been told there a thousand times. Or you might hear the anxious whisperings of a group of captains who sat up all one fateful night in April 1912 awaiting a special edition of the newspaper. The unsinkable Titanic had struck an iceberg and sunk. The noted Ship owner E.G. Crosby was aboard, would his name be among those who lost their lives? It was.

Today, we're certain: ghosts from those long-ago years still haunt Sailor Ann's."

By the mid-1950s, there were other places where men seeking men could gather, and Sailor Ann's time as a "sailor bar" quietly came to an end.

"You could always find a sure thing at Sailor Ann's," said George "Bunny" Opper. "It was well-known as a safe harbor for men of a certain age. After the remodel, it was just another steakhouse. It lost all the luster and the lust that made it famous!"

Sailor Ann's made national news again in May 1954, but not for its history or heritage. After $1,200 went missing from a locked business vault, local police found the safe's combination visible on a calendar hanging above the safe. Gerritt Stell admitted to Time Magazine that he'd written it down after repeatedly forgetting it.

Gerritt Stell died in January 1960, leaving behind seven children and a struggling business. On July 1, 1962, the City of Milwaukee denied Sailor Ann's license because its operators could not afford the tavern licensing fee. The saloon went dark for the first time in over 60 years.

"Sailor Ann's, once colorful and boisterous, faces a dark and uncertain future," wrote the Milwaukee Sentinel on July 27, 1961. The Stells blamed the recession for the restaurant's failure, as well as the rise of television. True, downtown nightlife was hurting, and Sailor Ann's left-of-center location in a declining neighborhood couldn't have helped.

Jerome Stell was hopeful the bar and restaurant would reopen soon under new management. Instead, the contents of Sailor Ann's were sold at auction in September 1963 and the 72-year-old building was demolished in October 1964. It's been a parking lot ever since.

Sailor Ann's queer legacy lived on- shortly- at the nearby corner of 2nd and Florida. After successfully relaunching the controversial Black Nite (400 N. Plankinton Ave.) as the Bourbon Beat, operator Wally Whetham opened the Captain's Cabin at 400 N. 2nd St. According to reports, he completely refurnished the space- a former "Gay 90s" saloon -- with Sailor Ann's artifacts bought at rock bottom auction prices. Unfortunately, the Captain's Cabin closed during Whetham's December 1966 bankruptcy proceedings, and the whereabouts of those historic furnishings have been long unknown.

The adjoining property (234 W. Florida) was completely renovated in 2008 and now houses a variety of modern commercial and residential spaces.