Captain Brantley's grandson put me in touch with Bob Winchester, son of Shot Winchester, owner of Club Winchester. Bob has quite a few chips used at the club. We had a good talk but he did not want to sell the chips. He sent me scans. They looked very familiar to me but I did not have them. I uploaded them to the BB and got an email about them. Turns out Mike Vuolo had some and had offered them to me. Diamond mold with CW on them. At the time I turned down the offer as I had way too many UFC's.

Mike got the CW chips from a Michigan seller on ebay. Bob Winchester told me a former Club Winchester bartender also had some chips but had moved to Michigan. What goes around comes around. Mike furnished 5 sets for the IOTD team. That's enough back story, enter Ed Hertel and the "Rest Of The Story."

The story of Lester “Shot” Winchester starts with a literal bang, and really never seems to let up. Born right before the turn on century, Lester grew up fast in southern Illinois’ little town of Vienna. At the age where most people are worried about middle school, Lester was busy working the streets. By the time he was fifteen years old he was hustling dice games and was about to have his first major run in with the law.

What started the argument isn’t in question. It was during one of these street craps games that Winchester felt he was being cheated and demanded both his lost money and an apology. After being offered neither, Winchester left the scene in a fury. When he returned a little later, he walked up on the group and unloaded a shotgun into the other young man, killing him instantly.

There was really no defense and he was found guilty and sentenced to 38 years. This should have been the end of his story, however Lester Winchester turned out to be a model inmate. He worked hard on the prison grounds and earned the respect of the officials. When an opportunity came to volunteer for an experimental malaria drug in exchange for time off his sentence, he jumped at the chance.

After serving only nine years, Lester Winchester walked out of the prison in 1922, still a young man ready to start fresh (although it’s said he lost most of his hair due to the experimental drug and never got it back!)

Making money in southern Illinois was easy for someone willing to get his hands a little dirty. It was during this time that the area was being fought over (quite brutally) by rival gangs – mainly the Sheldon gangs, Frank Wortman’s (with the help on Al Capone’s gang) and the ever dangerous Purple Gang. Lester “Shot” Winchester sided with the Sheldon gang and was one of their more confident moonshine runners. He did this with great success and made a lot of money, but this wasn’t his dream. What he really wanted was to own a night club.

My note: All three of these gangs and their bloody campaign to control the illegal gambling and cat houses in Illinois have appeared in several past "Illegal Of The Day" posts.

Winchester’s opportunity came in the 1930s when he opened his Casino Club in Karnak, Illinois. Like most of the small southern Illinois towns bordering Kentucky and Missouri, Karnak was a hot spot for illegal gambling. The Casino Club was located at the intersection of Rts 37 & 169 and, like its neighbor the Spur Inn, offered food, liquor and gambling.

My note: I need the Rectangle Heart chip. Cough it up if you have traders.

This club however was not the culmination of Shot’s ambitions, but only a stepping stone to something grander. By the mid-1940s, his focus turned to nearby Olmsted, Illinois, where he built his dream. When the Club Winchester opened with much fanfare in 1946, Shot must have felt like he had finally made it. It was reported that the nightclub was the biggest south of Chicago. The bar area was plush and decorative and the entertainment areas was covered in acoustical tiles for enhanced sound.

The basement was where the liquor and gambling equipment was held. Although out of sight, it was well known what was happening there. The governor would fine the Club Winchester, along with the many other casinos, every few weeks as a show of concern. The amounts were small and the clubs simply accepted them as the price for doing business. As long as nothing big happened, and everyone played the game by the same rules, the money train could continue. But that wasn’t in the cards.

Chips used at Club Winchester:

The game changer came in 1948 when Adlai Stevenson defeated the incumbent governor and immediately went to work against vice in Illinois. Stevenson could make the fist, but he needed someone to actually throw the punch. That guy would be our friend, Captain Elza Brantley.

Captain Brantley’s exploits have been well documented in Gene’s multi-part IOTDs already. Suffices to say, the Club Winchester did not hold up any better than the other hundreds of places Brantley’s troops menaced. In August 1950, the Club Winchester was hit with its most destructive raid as Brantley’s boys forced their way into the gambling room and set their axes to the furniture. What they didn’t hack up they dragged back to town for a public bonfire.

The increased legal pressure was starting to take its toll on the local clubs. Shot had already sold his first place, the Casino Club, in 1949, and now he was having trouble at the Club Winchester. The threat of raids caused him to close the casino to all but a small set of regulars. On top of that, the irregular closings due to court mandated padlocking made it difficult to book entertainers. Shot’s cashflow dwindled until he simply couldn’t keep the doors open. In 1952, the Club Winchester closed its doors for good. Its furniture was sold and the building purchased by the Sinclair Oil Company. Shot’s dream club was no more.

Down, but not out, Shot Winchester pulled himself up by his bootstraps and gave it another go. He knew he couldn’t make a plush nightclub work in this environment, so he scaled in down - way down. In 1953, along Route 37 in Olmstead, popped up Shot’s new Club 37. Gone was the big stage and orchestras, replaced instead with a jukebox. No more would the crowds of out-of-towners and big spenders be catered to, but instead his clientele would be more casual and family friendly. Whether or not there might have been some gambling in the back… I can’t say (although I kind of hope there was.)

My note: As stated in the past, I did not get copies of all on Captain Brantley's notes. I was told I had all that mentioned raids on gambling joints. At this point I would say that is not correct. My notes does not mention Club Winchester raids. Club 37 is noted as a raid. I would say they had gambling of some type. A couple Club names were read to me in phone calls.

Shot’s new life as a scaled down club host was working, but if he thought his life was going to get easier, he was terribly mistaken. From this moment on, Lester “Shot” Winchester’s life would be on a furious downward spiral that would end like so many hustlers before and since.

In July 1955, Shot was slapped with nine counts of receiving stolen property. The facts have never been firmly established, but somewhere between the truth and trumped up charges lays the answer. What is clear is that stolen goods were found on Winchester’s property. What also seems clear is that Shot had made some enemies with the local law enforcement. He claimed he was set-up, while the police said he was a fencer for stolen goods. Only a court date (that would never come) could have settled it.

Further trouble didn’t take long to find Winchester. On the night of February 23, 1956, the little community of Olmsted was shocked when news started circulating about a brutal murder at a nearby club. Clate Adams, owner of the Tin Inn, had been shot twice in chest and once in the back for unknown reasons. It didn’t take long for the police to find the man responsible and punish them adequately. Buried under a mountain of evidence, he pled guilty and receiving a 180 year sentence. What seemed like an open and shut case was anything but. He had a story to tell and the courts were ready to hear it. He said while drinking at the Club 37, Shot Winchester told him that Clate Adams kept $12,000 in cash at the Tin Inn and they should get it. Hours later, Clate was dead.

Friends of Winchester deny any such conversation took place and that the story was invented in an attempt to get a lighter sentence. Either way, the courts wanted to hear Winchester’s side of the story. A bench warrant was issued and county police fanned out to find Shot Winchester. After a day of fruitless searching, they received a call from a nearby farmer saying he had found a body in a car. When police arrived, they found Lester “Shot” Winchester slumped in the front seat with a fatal bullet wound to the head.

Winchester’s death was suspicious, no doubt about that. The gun found beside his body had three shots fired – two through the windshield and one to his head. The most popular motive for murder was that Winchester was silenced to prevent him from talking to the grand jury about the various vices in town. Whether or not he was involved in these activities, he did know all the players and could potentially be a liability.

The county however came to a different conclusion – suicide. Shot’s wife had testified that he declared he would rather kill himself than go to prison. This was backed up by Bill Harris, Club 37’s bartender and good friend of the Winchesters. What the true story is we may never know. A grand jury was called to look into the case further, and although it recommended that the county open the case back up, nothing was pursued. It seems that the powers-that-be were fine with letting it rest.

Lester “Shot” Winchester was 59 years old when he died. His life certainly wasn’t easy and serves as a window into the times of southern Illinois lawless days and the consequences of living in it.

If you are interested in a more information about Shot Winchester and life in southern Illinois’ vice, pick up “Sins of the South” by Maureen Hughes. I plan on doing a review to this book in a reply to this IOTD.

My note: Captain Brantley and the stories of his raiders may never end as far as the "Illegal Of The Day" series goes.

Mike Vuolo has some of the CW chips for trades.

"Illegal Of The Day" ALERT! New Ohio illegals have been found. Story coming in the next IOTD.