15/02/2026
In London, in 1888, Jack the Ripper was in the headlines repeatedly. On the other side of the Atlantic, we had Jack the Hugger, Jack the Pincher, Jack the Squeezer, Jack the Kisser and even Jennie the Hugger. There were reports from cities and small towns around the country of these attackers at work.
Freeport did not escape this phenomenon. In 1891, we started out with Jack the Peeper. There were reports of ladies seeing a face staring into their bedroom windows. Several husbands gave chase, but the Peeper was not caught. He seemed to be quite active in the Clark St. area, and was not particular who he was peeping.
Soon, Jack the Hugger appeared in Freeport. Usually he would hide in the shadows, or behind a tree, and jump out at ladies passing by. He wasn't reported to be intent on robbery or causing bodily harm, he just seemed to consider it a challenge to hug and run. The ladies being startled would usually scream and flee.
In 1897, Jack the Kisser appeared on Lincoln street where he would rush from his hiding spot, kiss the girls and run away. The police were actively looking for Jack and arrested the dog catcher, Charles. He was given the choice of paying a fine of $25 or spend 50 nights in the local lock-up. He chose not to pay the fine. I would think that everyone in town knew who the dog catcher was. What was the reaction of the citizens?
In 1895, in Cloquet, Minnesota, Helen Leonard was a "typical new woman". When Alexander Adams came up from behind her, she "squared off like a prize fighter" and gave him two black eyes and a general beating. Some of the ladies in Freeport took note and started fighting back. One of the young ladies walking down Carroll Ave. took offense to Jack's attentions and "slapped him squarely" across the face. Another lady used her hat pin to send her hugger running.
It seemed like the ladies in Freeport were believed that the attacks were real happenings. But if there was an arrest, in the early years, the Jack was usually let off with the promise of not doing it again. If the Jack was not from Freeport, he was usually sent packing and told to never return. The fines increased from $25 to $50 and even an occasional award was offered.
Jack the Hugger, in Freeport, was described as being "small in stature, shabbily dressed, with light brown hair and moustache". Another Jack was described as a man of medium height, smooth shaven, corduroy hat and coat, carrying a dinner pail and of middle age.
One gentleman passing through Freeport was arrested for scaring several ladies "nearly to death". He denied being the Hugger but paid a $25 ($860+ now) fine just to save time and trouble. He was a well-to-do farmer from Southern Illinois traveling to Iowa for business. I doubt he got off the train in Freeport ever again.
In 1905, Jack the Hugger struck again on North Galena Ave. This time he embraced an elderly lady who screamed, drawing the attention of a "gallant young man" who gave chase. Jack was caught near Douglas St. where he was administered a "sound thrashing" and left with a battered face and clothing.
Mrs. Neidigh and Miss Rae Boyington were the victims of Jack near River School. (VanBuren & Ringold area) Seldom were the ladies identified by name in the paper.
In 1907, the paper reported another attack on North Galena near Hardin St. A local man had been watching someone in the distance acting strangely. He had been moving in the shadows from tree to tree trying to keep out of sight. The local man gave chase and caught the stranger who was later identified as a contractor living in northwest Freeport with his family. He promised to never do it again and was left go. The only problem was - it was never reported to the police. Was it a real happening or was it a "story" for attention?
These reports went from the 1890's into the mid 1920's. Jack seemed to move from the bigger cities, to Freeport, and then to the small towns like Lena, Elizabeth, Dixon........ Were they copy cat Huggers? Did they read of other incidents and decide they would give it a try? Did the ladies start fighting back because they were getting more forward/modern?
Fact is stranger than fiction - sometimes even in Freeport of long ago.
