Pogy Bill Married Eddie Merle Dupree, the daughter of Horace Dupree, in the early 1920’s. The couple never achieved financial security because Bill so often took it upon himself to provide for the needs, often with the last cent in his pocket. Everyone who remembers the colorful lawman, recalls that he as perpetually broke, for he gave away all that he made. He was the unofficial daddy to every orphan in the county. Widows and families in distress were likely to find themselves the beneficiaries of his charity.

When prohibition became the law of the land, Pogy Bill found himself in contempt of the law. He had quit drinking many years before, but he saw no harm in a person taking a drink.

At this point in Okeechobee history, fishing was no longer a profitable enterprise. The existing cattle business required few employees. The woods were almost hunted out. The only thriving industry was lumber, but the local sawmill brought in its own labor. Pogy Bill knew that a great number of Okeechobee residents derived their income from making and selling moonshine. The dense undergrowth around the lake made the scrubs and hammocks ideally uited to setting up and concealing stills. Some books and periodicals record that the county was alive with stills.

On one occasion, it was reported to Sheriff Pogy Bill that a large still had been located. He assured them that he would get around to investigating it, but at the moment, he said, he was "spending all my time trying to keep those fellows from selling the stuff in the post office."

He couldn’t and probably didn’t even want to stop all the production and sale of moonshine in the county, since he knew many people depended on this industry for their livelihood. He also didn’t let the moonshingers run wild. In usual Pogy Bill style, he supervised the illegal activities, according to his own code. Unfortunately, his system did not exactly comply with federal regulations, and Pogy Bill found himself under investigation. His arrest involved a still in the woods northeast of the town. The tracks for the St. Andrews Bay Lumber Company trains ran right past the still. Allegedly unknown to the officials of the lumber company, these trains had been hauling in sugar and meal and hauling out the moonshine in barrels, concealed under the lumber.

One of the New York shipments sprang a leak in the railroad yards at Lake Wales. Government agents began an intensive investigation, and while they were not able to find evidence to charge Pogy Bill with manufacturing the moonshine, they did charge the sheriff and one of his deputies with guarding the road while the illegal booze was being loaded onto the train. In 1931, he was tried twice in Miami. The first trial ended in a hung jury. The second jury found Bill guilty on three counts, each carrying a two-year sentence. He appealed the conviction, and although the original verdict was upheld, he was placed on six years probation.

He resigned from the office of sheriff. His resignation came about not as a result of public pressure, but because he wanted to save Gov. Doyle C. Carleton embarrassment. In fact, the Okeechobee community sent the governor a petition urging the governor not to accept the resignation. It was signed by 700 persons, representing about 90 percent of the county voters at that time.

In 1932, he ran again for sheriff, and for the first time in his political career, he was defeated by three votes. His trial and attorney fees had cost him what little he had. He had sold his car and campaigned on foot. He took a job for a while in Indiantown, and when the office of Chief of Police in Frospoof became vacant, he applied for and was appointed to the post.

In 1934, while on his way to a fire, an accident left Bill pinned under an overturned firetruck. He was apparently unhurt at the time, but several days later, he caught pneumonia and died.