Colorful Characters in Phelps History

“Homeless Homer” Galpin – Chicago Bootlegger or Early Phelps Marketer?

The development of our great town of Phelps is often credited to the logging industry that thrived throughout Vilas County in the 1800’s. However, it could be argued that Phelps would not have developed into the travel destination it is today without the foresight and support of early enthusiasts like Homer K. Galpin. Despite questionable political practices and associations, Galpin succeeded in making Phelps the favorite, and exclusive, weekend retreat of Illinois businessmen, while giving Phelps a colorful history to debate for decades to come!

A Political Path of Success and Suspicion

Homer K. Galpin, or “Homeless Homer” as he was later dubbed, was born in Chicago in 1871. After graduating from Lake Forest University, Galpin joined the Illinois bar in 1893 and began practicing law. In 1899, by which time he had already begun visiting the Phelps area, Galpin was elected as the Cook County Board of Review clerk, thus starting his career in Chicago politics.

Galpin continued to develop as a major Republican Party political figure and was even elected as a state senator, although he resigned before trouble arose regarding his holding two political offices and collecting double pay. He became the chairman of the Cook County Republican committee in 1928, the same year that his ethics came under question. As manager of Chicago Mayor William “Big Bull” Thompson’s campaign funds, Galpin was thought to be guilty of accepting money from gamblers, bootleggers, and mob affiliates. He himself was accused by opposing parties of being the boss of eight major bootleg breweries!

Because of Galpin’s involvement with the corrupt mayor, he was issued a subpoena to testify in Cook County regarding the campaign funds. He managed to avoid this subpoena for two years, by hiding out in Phelps during the summer and in Sarasota, Florida through the winters. Despite this questionable affiliation, Galpin was later appointed to the Illinois Tax Commission and continued to be active in Chicago’s Republican Party.

Laying Down Roots in Phelps

Throughout his political career, Galpin continued to frequent the Phelps area on weekends and summers. In 1903, Galpin was elected president of what is now the Big Sand Lake Club and began throwing roaring parties for his big-time Chicago friends. The Illinois visitors, some suspected to have mob backgrounds, loved the seclusion and rustic atmosphere of the men-only club and the Phelps area.

Galpin held the position of club president three times, and remained a steady supporter of the Big Sand Lake Club throughout his life. To make the trip from the Chicago area more comfortable, Homer campaigned for and succeeded in bringing sleeping car rail service to the small town. This made it easier for even more vacationers to enjoy the stunning natural beauty of Phelps.

In 1916, the same year Galpin married his second wife, Hilda Jensen, he purchased 700 acres on the south shore of Big Sand Lake and began work on what would become one of the richest estate in Phelps. He continued to entertain Chicago businessmen, both at the Big Sand Lake Club and his private residence, until he fell ill at his Phelps property in 1941 and passed away.

Phelps Today – A Four Seasons Destination

Galpin’s efforts to establish Phelps as a premier destination spot is still evident today. The Big Sand Lake Club continues to be one of the finest private resort retreats in the area, over a hundred years after its creation. Fishermen, families and wildlife enthusiasts continue to enjoy the many lakes and nature opportunities of Phelps, many even laying down roots with summer homes like Homeless Homer. The peaceful beauty and seclusion of Phelps that Galpin first appreciated in the 1890s still flourishes today!

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