The Last Oshkosh Bootlegger

Adolph Seibold got caught on Jackson Street trying to move 1,700 gallons of moonshine. The arrests that followed triggered the downfall of the largest syndicate of bootleggers in the State of Wisconsin. Seibold had been flirting with this kind of trouble for years. You could see it coming from a long way off.

 Adolph Seibold

A Son of the Southside
Adolph Seibold Jr. was born in Oshkosh in 1894. He was the second child of Adolph Seibold, a Bavarian immigrant, and Theresa Mueller Seibold, who migrated to Oshkosh from Bohemia. The family lived in a home that still stands at what is now 423 W. 14th Avenue.

The Seibold family home, ca 1935.

Seibold quit school at 15. Like his father, he got a job at a woodworking mill. But the Morgan Company couldn’t hold him. Adolph possessed a restless energy. It led him to a more stimulating job at Chris Genal’s saloon on Oregon Street.

1309 Oregon Street, the former saloon of Chris Genal.

Genal’s saloon was launched in 1891 by a beer bottler named Frank Lutz. Around 1904, a pair of bowling alleys were grafted onto the back of the building. The Rahr Brewing Company bought the bar in 1913, turned it into a tied house, and installed Chris Genal as the proprietor. Genal renamed the saloon Elk’s Head Alleys. The name change was probably at the behest of the Rahrs, who had just come out with Elk’s Head Beer. Seibold was there by 1917, slinging mugs of Elk’s Head.

From a 1916 advertisement for Rahr’s Elk’s Head Beer.

Seibold’s first stab at his new vocation came to a sudden end in 1918. It was a hell of a year. In mid-April he got his girlfriend pregnant. She was a 23-year-old northsider named Maude Zwickie. Adolph wasn’t around to see the birth of their child. The conception had coincided with the arrival of his draft notice. July found him in France flung into World War I. Seibold may not have known he was going to be a father.

He was assigned to the 6th Division’s supply train and sent to the Western Front. There he endured the Meuse–Argonne offensive, the deadliest battle in the history of the United States Army. More than 350,000 casualties were suffered in 47 days of non-stop fighting. Seibold’s luck held. He came through the war unscathed.

Adolph Seibold in France.

On June 10, 1919, Seibold boarded a ship in Brest, France and began his journey home. He was back in Oshkosh by early July and finally met his daughter Dolores. She was six months old. And at the end of August, Adolph Seibold and Maude Zwickie were married.

Maude and Adolph, seated on their wedding day.

Outlaw
Seibold returned to a land less free than the one he left in 1918. While he was away, the Federal Government imposed the Wartime Prohibition Act, a draconian measure aimed at crippling the saloon trade. And then came national Prohibition in January 1920. Seibold’s vocation was outlawed. He would be an outlaw for the next 16 years.

His old job at Chris Genal’s saloon was waiting for him. Only it wasn’t a saloon anymore. It was a speakeasy. Rahr Brewing still owned the building, but it was up to Genal what to do with it. What he did was get busted.

State prohibition agents raided Genal's place in early February 1924. They uncovered a cache of wine, and arrested Chris Genal in his apartment above the bar. In court, Genal said the wine wasn’t his. He said the bar wasn’t his either. Adolph Seibold had taken over. The judge told the prosecutors to get their story straight. The case fell apart, and the charge was dropped.

Seibold’s first brush with the sponge squad seemed to bolster his enthusiasm for bucking Prohibition. Elk's Head Alleys ran wide open every night of the week. It was also around this time that Seibold became acquainted with the Wainer Gang.

Oshkosh Daily Northwestern, March 27, 1924. The clipping shows the old address of 1308 Oregon. The address became 1309 Oregon after  the city's 1957 lot renumbering.

The Wainer Gang
The Wainer Gang was formed from a tight group of New London cattlemen making hay from the mire of Prohibition. It started with two Russian-born brothers: Hyman, better known as Heinie, and Louis Wainer. Their younger brother Sam was soon part of the mix, along with the Blink brothers, Donald and Earl. The Blinks had connections in Oshkosh and may have been responsible for bringing Seibold into the fold.

The Wainer Gang got into bootlegging with a cow and false-bottom cattle truck. They’d transport moonshine in one-gallon cans hidden under the truck’s false deck. The cow stood on top acting as a blind. The beast acquired its own degree of underworld fame becoming known as the state’s most traveled bovine.

The Wainers were soon running scores of trucks hauling liquor from stills in Antigo, Appleton, Fond du Lac, New London, and Galesburg, Illinois. The Appleton still alone consumed over 275,000 pounds of sugar a week. The enterprise grew into Wisconsin’s largest bootlegging ring, and became known as the Fox Valley Liquor Syndicate. By 1925, the syndicate’s moonshine, beer, and wine were being sold across Wisconsin and into Illinois, Iowa, Minnesota, Nebraska, and the Dakotas.

Exactly when Adolph Seibold came on board is not known. He appears to have been at least somewhat involved by 1926. By 1929 he was in deep.

Adolph Seibold in the late 1920s.

Seibold ran the Oshkosh hub of the Fox Valley Liquor Syndicate from a backroom at Elk's Head Alleys. The liquor was routed through a 13-acre farm Seibold bought one mile north of Oshkosh. He told his neighbors that he intended to raise guinea pigs on the farm. He did, in fact, keep guinea pigs, but the rodents served the same purpose as the Wainer’s cow. The little pigs were there to distract from the main objective: the distribution of bootleg alcohol.

Seibold’s Farm just north of Oshkosh where US Highway 41 now crosses Highway 110.

All In
Maude had given birth to their second child, Arthur, in 1921. In 1928, the family moved into the apartment above Elk's Head Alleys. But by the spring of 1930, running the syndicate’s liquor, the speakeasy, and bowling alley proved to be more than Seibold could keep up with. The real money was in the booze. So he sublet the bar to his friend Joe Dichtl and concentrated on bootlegging.

Seibold was enjoying the fruits of his risky business. He purchased property at Plummers Point on Lake Butte des Morts where he kept a summer cottage and boat house. But the money brought with it an ever-present sense of jeopardy. The threat was nearly realized in the summer of 1931.

Oshkosh Daily Northwestern, August 26, 1931.

When federal agents swept into Oshkosh on August 25, 1931, they went directly to Seibold’s farm. They discovered a few guinea pigs and 159 gallons of alcohol worth almost $2,400 (or about $47,000 today). They also uncovered more than 4,000 empty tins used for transporting moonshine. What they didn’t find was any trace of Adolph Seibold. The feds claimed that a boy was in charge of the farm and that he ran off before they could grab him.

The agents may have been told to get their noses out of Seibold’s affairs. The Fox Valley Liquor Syndicate’s influence allegedly extended deep into the ranks of law enforcement, on both the local and federal levels. In this case, payoffs may have paid off. Though Seibold owned and operated the farm, his name never came up in connection with the raid. The entire matter was dropped.

Family Man
All the while, Seibold’s family life continued apace. When his mother died in 1931, he moved his family out of the apartment above the speakeasy and into the 14th Street home where he had been raised, and where his father still lived. Adolph’s father would reside with them for the remainder of his life.

Adolph Seibold Sr. at the family home on 14th St.

Adolph Seibold Sr. was born in 1864, and was a Bavarian farmer before coming to America at 19. He could hardly have imagined the things 1931 would show him. In his homeland they were falling under the spell of a lunatic named Adolf. Here in Oshkosh, he lived with an American outlaw named Adolph. His son, at least, didn’t trade in the hate that came to be associated with the name they all shared. Adolph Seibold’s partners, the Wainer brothers, were Jewish.

The Seibolds were Catholics. The kids went to school at St. Vincent’s. Aside from Adolph’s underworld occupation, the Seibolds were like most other Southside families. Maude gave birth to their third child, Kenneth, on January 12, 1933. But again, Adolph was taken away when she needed him most.

Friday the 13th
On January 13, 1933, the Fox Valley Liquor Syndicate sent an enormous haul of moonshine through Oshkosh bound for Illinois. It came in what was later described as “a brand new super-size truck and trailer.” The truck carried 31 metal barrels, each holding 55 gallons of moonshine. In all, it was worth about $26,000 (close to $590,000 in today’s money).

Earl Blink drove the truck. Sam Wainer, acting as guard, tailed him in a sedan. The truck broke down on Jackson Street as it approached New York Avenue.

Sam Wainer called for help. Shortly after, another syndicate truck arrived. It was never determined how or when Seibold came on the scene. He may have been traveling with either Blink or Wainer. Or he may have driven the replacement truck. In any case, the three of them went to work transferring the moonshine into the new vehicle.

Each barrel weighed near 500 pounds. It was close to midnight. They didn’t know that federal agents were trolling in Oshkosh. They found out the hard way. Blink, Seibold, and Wainer got snared when a car carrying two agents came cruising down Jackson. The feds knew at once that they had landed a big one.

Appleton Post-Crescent, Saturday, January 14, 1933.

All three were arrested and taken to the city jail. Seibold protested. He told the feds he was an innocent bystander, a good samaritan helping a couple of fellows in need. Sam Wainer gave them a false name. The young Wainer was in a bad way, with an outstanding violation from a raid on a New London whiskey depository six months earlier. Another charge would mean jail.

The agents knew they were onto something more than a local moonshine outfit. They called in the head of the Milwaukee bureau. He arrived the following morning and identified Sam Wainer, calling him “One of the bigshot bootleggers in Wisconsin.” The downfall of the Fox Valley Liquor Syndicate was underway.

Blink, Seibold, and Wainer were denied bail and sent to Green Bay. They were held over the weekend in the Brown County jail. They were arraigned in federal court on Monday afternoon, charged with possession and transportation of alcohol. Later that evening, all three were granted bail and released. Adolph Seibold went home to Oshkosh and met his new son.

Adolph Seibold with his son Kenneth.

The Syndicate
Back in Oshkosh, Seibold was at loose ends. He had a wife, three children, and a father to support. And no job. He couldn’t go back to the speakeasy. Even a minor liquor violation would land him in the House of Corrections. But at the end of 1933, the scene changed. Prohibition was repealed on December 5th. And in 1934, Seibold went back behind the familiar bar at 1309 Oregon.

Adolph Seibold behind the bar at 1309 Oregon. Photo courtesy of Jen Seibold.

The dry law was nullified, but Seibold’s dry-law offense was not. He could do nothing but wait for the hammer to drop. Meanwhile, the feds were putting all of the pieces together. It wasn’t just Adolph Seibold, Earl Blink, and Sam Wainer they were gunning for. They were going after the entire Fox Valley Liquor Syndicate. By the end of the investigation, Seibold was one of 22 indicted co-conspirators. The only problem the feds had was getting them into court.

Sam Wainer and Earl Blink jumped bail and went into hiding. Then in early 1934, Heinie and Louis Wainer went on the lam. Heinie and Louis were captured nine months later. But while the brothers were away, their cohorts began telling stories to the feds. Their depositions revealed the unsparing tactics of the Fox Valley Liquor Syndicate. It all came spilling out when the trial finally began in federal court in Milwaukee on December 2, 1935; nearly two years after the fateful breakdown on Jackson Street.

The syndicate ran like a machine pumping torrents of liquor and kneecapping anyone who interfered. Witnesses told of severe beatings dealt to those who crossed the Wainers. And of threats made to local officials found sniffing around. The operation was byzantine. A complex web of warehouses, breweries, and distilleries operating at capacity. Syndicate liquor was distributed by rail and by trucks shadowed by armed guards.

Seibold clung to his “Good Samaritan” defense. And it got shot full of holes by witnesses who said his Oshkosh guinea pig farm was a ruse to conceal his role in the syndicate. He used a local produce dealer's rail account to ship moonshine and deliver corn sugar in boxcars billed for hauling vegetables. Seibold wasn’t implicated in the violence, but was exposed as a Wainer associate in every other respect.

As the trial went on, it became clear that the ultimate target was Heinie Wainer. He was the “Master Mind.” His brother Louis was the money man who financed syndicate members and handled payoffs. Donald Blink and his at-large brother Earl were the traffic managers directing shipments of equipment, supplies, and liquor.

The trial lasted four days. The jury deliberated for less than an hour. Of the 21 indicted, 14 stood trial. All of them were found guilty. Heinie and Louis Wainer were given six-year sentences in the Federal Penitentiary at Leavenworth, Kansas. Donald Blink got just three months in the Milwaukee House of Corrections. Adolph Seibold walked away with the lightest punishment of all, a $100 fine (about $2,500 in today’s money).

The Last Oshkosh Bootlegger
The Wainer’s attorney told his clients they’d get no more than four years in prison. The six-year sentence sent a shock through the courtroom. Heinie Wainer complained to the judge that he had “never heard anything like this before.” Equally shocking were the light sentences handed down to the other members of the syndicate. Seibold’s fine was a slap on the wrist.

The leniency may have inspired the retribution that followed. Donald Blink hadn’t even completed his three-month term before being dragged back into court on an older charge involving a distillery in Stevens Point. Don Blink was swiftly convicted. This time, the prosecution got the sort of punishment they were after – a one to two year term in the state prison at Waupun.

Adolph Seibold was next. State treasury agents raided his cottage at Plummer’s Point on the Monday afternoon of July 30, 1936. Just seven months after his conviction in federal court. When asked what inspired the raid, the treasury men said “numerous complaints.” End of story. They would not disclose the nature or source of those complaints.

The agents at Plummers Point canvassed the property and then honed in on the garage at the back of the lot. The Wainer Gang had been notorious for using false floors to conceal stockpiled liquor. The treasury men went at Seibold’s garage floor with a sledge hammer. The blows were fruitless. But while scrounging around in the boathouse they came up with a gallon and a half of moonshine hidden in a cabinet. It was hardly the bonanza they’d been seeking. They arrested Seibold all the same.

Seibold’s boathouse in the foreground at Plummers Point.

The agents should have pursued their initial hunch more vigorously. Seibold’s garage did indeed have a false floor. If the cops had been less busy with the hammer, they might have discovered the concealed switch at the back of the garage. Flipping it would have triggered a concrete floor panel on a hydraulic lift to descend, elevator like, into a hidden compartment below. In that space there are still barrels – now rusted and drained – of the type used by the Fox Valley Liquor Syndicate for transporting moonshine.

Seibold's trial was in Oshkosh on July 22, 1936. The prosecution pleaded with the judge to make an example of him, claiming Seibold was still running significant quantities of bootleg liquor. But the treasury department couldn’t produce an example of him selling the stuff. And the paltry amount of unstamped liquor they caught him with suggested he wasn’t much of a dealer.

Adolph Seibold had plenty of practice feeding nonsense to judges. He said he had no idea how that liquor had gotten into his boathouse. The judge dispatched the entire sorry mess by handing Seibold a $200 fine (about $4,300 in today’s money). Oshkosh’s last Prohibition-era bootlegger paid up and walked away one last time.

The irony of it could not have escaped him. His $200 fine for holding 192 ounces of moonshine was double the fine he got in 1934 after years spent handling thousands of gallons of illegal liquor. Adolph Seibold was about to turn 42. And he was finally done with all that bootlegging business.

Adolph Seibold at Plummers Point.

The Old Gang
Adolph Seibold began pouring his energy into his bar at 1309 Oregon. Rahr Brewing still owned the building, but Seibold treated it as his own. He remodeled the old saloon, took out the bowling alleys, and put in a dining hall that could seat 150 people. He renamed it Cy's Casino. The grand reopening of the “South Side’s Largest Tavern” was on December 17, 1936.

Seibold and his family left the homestead at 14th Avenue after his father died in 1942. They updated the cottage at Plummers Point and made it their permanent home. There have been Seibolds living at Plummers Point ever since.

The boathouse at Plummers Point.

In 1946, Seibold sold the guinea pig farm that had been the Oshkosh hub for the Fox Valley Liquor Syndicate. The property would later achieve a second round of notoriety as a “gentlemen's club” called The Loft.

The other members of the Wainer Gang made their way in and out of jail. After Donald Blink's release from Waupun, he moved into the apartment above Cy’s Casino and went to work tending bar for Seibold. His brother Earl Blink – who had been arrested with Seibold on Jackson Street in 1933 – remained a fugitive until 1937. In 1938, he was sentenced to six months in jail. Earl Blink later moved to Oshkosh and became a bartender at Cy’s Casino.

Sam Wainer, also arrested with Seibold in 1933, remained on the run until his capture in 1938. He would spend four months in jail and then move to Chicago. He was joined there by his brother Heinie. Heinie Wainer was fresh from Leavenworth and ready for action. He dove back into the underworld, peddling stolen liquor to taverns in the Chicagoland area. His career ended when he got gunned down by a rival at his Chicago apartment in 1959.

Hyman “Heinie” Wainer

Devil May Care
The crimes of the Fox Valley Liquor Syndicate and the Wainer Gang were front-page news in the 1930s. Some of the tales were told again in 1959 after the murder of Heinie Wainer. Among the scattered anecdotes was the Wainer Gang’s alleged war with Al Capone’s mob for control of the liquor trade in southern Wisconsin. These were stories Adolph Seibold never shared.

Adolph and Maude Seibold with their granddaughter Melissa, 1970.

Seibold rarely spoke of his experiences as a bootlegger. The crimes, the arrests, and the peril that stalked him during that era belonged to the past. He put all of it to rest.

But the devil-may-care spirit that marked almost everything Seibold did remained with him. He was 79 and suffering from a heart condition when he was admitted to Mercy Hospital on Hazel Street in August 1973. He did not want to be there. So he jumped out of a second floor hospital window attempting to get away. He didn’t get away. He broke his hip and died four weeks later. Adolph Seibold was buried in Oshkosh’s Calvary Cemetery on September 4, 1973.

At Plummers Point there are people who still tell stories about the bootlegger who lived in their midst. The stories are second hand, filled with gaps and hearsay. We can’t know what is lost. Most of what Adolph Seibold saw and did during the dry years remained known only to him. He took those stories to the grave.

About this story...
I first came across Adolph Seibold in 2015 while researching another story. I’ve been picking up bits and pieces about him ever since. This past summer, I was contacted by Melissa Seibold, a granddaughter of Adolph. She asked if I was aware of him. At that time, I knew only the outline of his life as a bootlegger. Melissa and I began talking, and she shared with me what she had heard of her grandfather. Those conversations set this story in motion. Melissa deserves the lion’s share of the credit for making this piece happen. I’m sure Adolph would be proud of her.

Adolph Seibold and his granddaughter Melissa.