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Winegar Reflections

Main Street Mayhem

Three people whom you have never heard of, and who have never lived in this town, played major roles in a potentially violent confrontation that took place right here on Main Street. Let’s travel back to July 19th, 1958, and see what happened….

John Chipman and Ray Emery, two semi-successful, low-life criminals, were, on that day, in the process of fleeing from the Minocqua Police. They were wanted for hundreds of break-ins in Crandon and Milwaukee, as well as several parole violations. Little did they know that, in just a few short hours, they would not be considered for any future parole for years to come.

After crashing through a roadblock set up by the Woodruff cops, they sped north on Highway 51, exchanging gunfire with the pursuing officers. Law enforcement agencies in two counties, as well as the State Police in Upper Michigan, were now involved to trying to capture them, as they were considered to be “armed and dangerous”. Police set up more roadblocks in the area, but the two felons somehow were able to avoid capture by traveling some of the many side roads in the area. Eventually their luck started to change and by the time they reached Annabelle Lake, just outside of Presque Isle, they were on foot. Hitching a ride the rest of the way into town, and seeing no cops, they stopped at the Winegar Tap, where Gunnar Larson served them a couple of cold beers. An hour later, after eating at The Lure (location is now the Wilderness Café), they decided to return to Gunnar’s for more drinks.

Which brings us to the third person in this event that you never heard of; a vacationing policeman from Bayfield County, Sheriff Frank Utpadel. He happened to be at the Winegar Tap when Chipman and Emery first came in, and recognized them from the descriptions being broadcast throughout the area. While the two were at the Lure eating, Sheriff Utpadel retrieved a Thompson sub-machine from his car, took up a strategic position outside, and waited for them to re-appear. By now, numerous police cars had shown up, and quietly surrounded the town. This was about to get real serious……

As the crooks made their way back toward the tavern, Sheriff Utpadel popped up from behind one of the parked cars and, pointing the Tommy gun, shouted “STOP WHERE YOU ARE, OR I’LL CUT YOU IN HALF!” Taken by surprise, Chipman didn’t even have time to reach for the pistol he had in his waistband. Slowly he, and his partner-in-crime, reached for the sky as the rest of the policemen swarmed in. By now, word had spread and it seemed like the entire population of Presque Isle had gathered on Main Street to witness the excitement.

Chipman and Emery were handcuffed and placed in separate squad cars. The townspeople then turned their attention to Sheriff Utpadel, declaring him a hero, and praising him for his single-handed capture of the two dangerous fugitives. The Sheriff and his wife were deluged with offers of free drinks, meals, and other amenities from a grateful village.

The unlucky lawbreakers were eventually convicted for their crimes, and spent the next few years as guests of the state prison. We are quite sure they never wanted to return to Vilas County again.

Thanks to the quick, cool thinking of Sheriff Utpadel, what could have turned into a bloody shoot-out on Presque Isle’s Main Street was avoided. In an upcoming article we will discuss a previous bloody confrontation between law enforcement and criminals that took place just outside of town, and resulted in fatalities on both sides. Stay tuned……

Information contained in these articles is obtained by researching various written sources, witness interviews, and personal recollections. Dates, places, and events, are believed to be as accurate as possible.

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