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The Chip Board Archive 21

Illegal Of The Day Wisconsin 4

I got the HOG chip from Mike Vuolo back in April of this year. The PDB chip came in a trade back in 2010. I feel certain there is a connection but at this time I have no real proof. Below you will read my “thoughts” at this time on the 2 chips and the connection. Elkhart Lake was a huge illegal gambling operation at the time both chips were delivered. There is a lot of info about the Elkhart Lake joints on the web.

Enough of that:


HOG-Per Mason records
R.J Demmings
Delivered to Elkhart Lake, WI
100 yellow-200 Blue-400 White
Rupert John “Happy” Denning, a Wisconsin native, died at Sheboygan in 1968 age 73.

pic of Denning from 1943:

Denning was a well known sportsman and café/tavern operator in the Sheboygan area for many decades. Unfortunately, I haven’t been able to determine what exactly he was doing at Elkhart Lake when the chips were ordered in July 1931, but he was probably associated with one of the popular summer resorts on the lake—many of which had big gambling operations.

In the early 1920’s Denning was associated with a place called the Calumet Inn, a popular night club and speakeasy outside of Sheboygan. Ad from 1924:

About a year after the ad Denning became partners with Kelly Howell in the operation of a place outside of Sheboygan called the “Red Feather.” In 1929 there’s a new sheriff in town and he raids this “notorious house of ill fame”

My Note: Let me think HMMMMMMMMMMMM.

Ok 9 people arrested for gambling devices and operating a house of ill repute. They paid a total of $600 in fines between them. The paper touts the fines were severe because they were arrested under “House Of Ill Fame” statute instead of “Disorderly House” statute. I guess the county would have owed the arrestees if not for the more severe statute arrest.

After the raid Howell re-opened the “Red Feather” as the “Casino.” Here’s a pic from 1929 when it was the Casino (look-up roadhouse in the dictionary and you’ll see this pic):

Denning does not appear to have been associated with the “Casino” but rather moves into Sheboygan, where by Dec.1929 he’s operating a place at 719 New York Avenue, next door to the Eagles Building. In the early 1930’s

Denning would move his place into the Eagles Building where he would operate until around 1943 (in 1943 he bought the “Esquire Tavern” which he operated until 1950).

My note: Operated next door to The Eagles from early 1930 them moved into The Eagles through 1943. HOG chips bought in July 1931. This is as close as we can come to putting the chips in use in one of Denning’s joints. I am calling them “The Eagles” with an asterisk. vbg

Read on, our “Friend Of the Hobby” says almost the same thing.

The Eagles
R.J Demmings
719 New York Avenue
Sheboygan, WI
100 yellow-200 Blue-400 White

A couple of ads from 1939:

When the chips were ordered in July 1931 Denning would have been operating The Eagles on New York Avenue, so I guess it’s possible that the chips could have also been used there. The chip delivery address says they were sent to Denning at Elkhart Lake, which at the time was a very popular summer resort (drawing a lot of people from Milwaukee and Chicago). Gambling was a very popular past-time there. Here’s a map from 1936 which shows its location relative to Sheboygan and lists some of the resorts which operated there (all were operating in 1931):

I guess the “O” on the chip could be for Osthoff’s—which definitely had gambling—but that’s a pure guess. Osthoff’s is still there: ).

I highlighted Crystal Lake as well because in 1939 Denning and Kelly Howell, his old partner from the “Red Feather,” began operating a place there called “Crystal Tavern.” Denning also had a summer home on Crystal Lake. Here’s an ad from 1940:

Here’s an article from the Milwaukee Journal from August 20th 1933. The article gives a nice description of what was going on at Elkhart Lake. I highlighted a paragraph which I thought was interesting. It says that the gambling concessions at Elkhart Lake were controlled by a big-shot from Sheboygan who spends his winters on the west coast. When I read this it reminded me of the PDB chip--which was sent to Peter De Braal at Sheboygan in 1932—De Braal used to spend all his winters in the Los Angeles area. Maybe the big-shot was De Braal???

My note: The paragraph he mentions is in first column marked with a grey brush mark.

drawing from the same page:

My note: Here is the bonus to this story. The PDB chip was supposed to have its own “Illegal Of The Day” post. I was hoping to come up with more info on DeBraal. Maybe we have found more info. The newspaper states the “Big Shot” of the area gambling operations wintered in Los Angles. DeBraal bought his chips in 1932, same time Denning operated The Eagles and he was a member of The Eagles.

Did we find our “Big Shot” or did DeBraal order some home game chips and take them to LA. Just wondering and no real proof of it.

In 1937 Peter DeBraal died of a heart attack in Sheboygan, age 56. The address on the chip card was his residential address. I could find no direct evidence of DeBraal being involved with any gambling enterprise. However, from 1914 through at least 1922 he was the proprietor of the Lake View Hotel in Sheboygan.

Built in 1895, the Lake View Hotel was originally owned by the Pabst Brewing Company; burned down in 1903; rebuillt in 1904; Pabst did not own it when DeBraal was the proprietor. The Hotel was a popular summer resort for visitors and a popular place for locals to dine and dance. Although I saw no evidence of it, it sounds like the kind of place that would have had some kind of gaming.

Unfortunately, there is no way that the chips DeBraal ordered could have been used there because the place burned to the ground in Nov.1929 and was never rebuilt. I suppose it's possible that DeBraal could have been operating games there and the fire destroyed his stuff and he had to order new chips in 1930, but where he used them is unknown to me.

When he ordered the chips he was a licensed real estate broker. At the time he ordered the chips, and for several years prior, he and his family spent the winter months on the Pacific Coast in Santa Monica guess it's possible he could have used them there. He was also a member of several fraternal societies in Sheboygan (including Odd Fellows, Eagles).

Messages In This Thread

Illegal Of The Day Wisconsin 4
Does anyone have.....
Re: Does anyone have.....
It sure looks like the same fonts here.....
Re: Dave Are You Aware
Thanks Gene I didn't know
Re: It sure looks like the same fonts here.....
Re: It sure looks like the same fonts here.....
Re: Illegal Of The Day Wisconsin 4
Re: Illegal Of The Day Wisconsin 4
Nice Post Gene, even if it is not Illinois vbg

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