1901 – 1918

Frank B. Tippins served with civility in a wild era for law enforcement during his tenure as Lee County Sheriff. Despite shootings, stabbings, jail breaks and other mayhem, the Sheriff was fearless and rarely carried his service weapon – he didn’t like a pistol flapping at his side and found it unnecessary. In fact, he only had to use his weapon twice in his career, which ultimately was eight terms as Sheriff, according to news reports. He even took to local waterways to enforce strict fishing laws, which included making arrests for fishing out of season and using nets that were more than 350 yards in length.

Florida increased the authority of local sheriffs in the first two decades of the 20thcentury, according to “Florida Sheriffs: A History 1821-1945,” including the authority to approve bonds and fix the fees of suspects, carry weapons without giving bond and request compensation for a wide range of services provided.

The construction of Highway 80, or Palm Beach Boulevard, began in 1905. Until 1900 the county commissioners did nothing to improve the oxcart trails of previous years, and Fort Myers was almost isolated from the world. Then, a mile stretch leading eastward from Billy’s Creek was laid with shell to cover the two foot wide and six inch deep oxcart tracks. To save money the commissioners voted to do the work themselves rather than to award it to a contractor.

Fort Myers evolved into a shipping hub for outbound produce and incoming agricultural supplies. The City Dock at the foot of Jackson Street was an elaborate structure extending far out to the river’s deep water. It housed a variety of services, such as a fish market, Chinese laundry, machine shop and boat ways, according to the National Sea Grant Library. With the arrival of the railroad in 1904, packing houses accommodated produce shipped downriver.

Transportation and infrastructure continued to improve during this time. Highway enthusiasts began to dream of a road that would lead from Tampa and through Fort Myers to Miami – the Tamiami Trail. In 1912 the county agreed to assist Mrs. M.O. Terry to build McGregor Boulevard from the train depot in Fort Myers to Punta Rassa. The road was named for her deceased husband, Ambrose McGregor. In 1916, a special road and bridge district was set up to build a road from Buckingham through LaBelle and Fort Thompson to the Palm Beach county line. The population grew steadily as infrastructure improved. Lee County grew from 3,071 residents at the turn of the century to 6,294 in the following 10 years, according to the U.S. Census Bureau.

Sheriff Tippins had an indirect role in the final days of Edgar J. Watson, immortalized by Peter Matthiessen in his novel “Killing Mister Watson.” Watson traveled from Chokoloskee to Fort Myers in October 1910 to report the deaths of three Monroe County residents. Sheriff Tippins returned with Watson to the Ten Thousand Islands to investigate, but Watson then left on his own and returned with the accused killer’s gun and news of his death. An accomplice to the triple murder was captured while Watson was gone. He claimed Watson forced him to assist in the murders.

A posse soon confronted Watson and demanded Watson bring them to the body of the accused killer. Watson refused, and after attempting to fire on the posse, the mob killed him. The posse then went to Watson’s plantation, where the accused triple murderer was found and shot to death while trying to escape.

Sheriff Tippins was known for his “jaunts,” the first being in November 1918 after five consecutive terms, to work for the Pinkerton Detective Agency and track down a man who robbed a LaBelle bank. “Tippins knew the robber, so Uncle Frank as we called him later in his years, took off after the robber,” according to the memoirs of Flanders “Snag” Thompson, who served as Sheriff between 1949 and 1973. Tippins eventually apprehended his man in Washington State, and turned him over to the federal government. Historian Karl Grismer in “The Story of Fort Myers” states that Tippins became a deputy Internal Revenue Collector to help break up bootlegging prevalent on the U.S. West Coast.