Phil Kelley; The Bow Tie Man of Osceola

Phillip “Phil” Russell Kelley didn’t always wear bow ties but beginning in the late 1950s; it appears to have become part of his regular attire. What prompted him to make the switch from a regular tie is a mystery, but Phil was definitely one of Kissimmee’s unique citizens. And with a good old Irish name like Kelley, Phil also had the “Gift of the Blarney.”

The Younger Years

The only child of Clyde and Marie Kelley, Phil was born on December 8, 1914, in Unionville, Missouri. He grew into a freckle-faced redhead who wasn’t afraid to work. During the Depression, he sold popcorn at the theater, enticing people to buy a bag by giving out free samples. When Phil entered Northeast Missouri State College (NMSC), he was active in several clubs, lettering in baseball. When Phil was president of his fraternity, his brothers talked him into inviting Hedy Lamarr to their Spring Frolic dance in 1939, but it appears she declined.

Military Man

Although reluctant to join the army, his tour of duty became an adventure and left him with a “fear of flying.” As a special agent for the Army Counter Intelligence Corps (CIC), he investigated treason, espionage, sabotage, violations of security, and handling classified material. His involvement in the College Players at NMSC came in handy when he assumed different identities during his investigations. Phil never revealed much about his CIC work but did relate how he pretended to be a plumber once to get into an apartment where a picture of Hitler was reported to be hanging on a wall. His reluctance to flying came from investigating military crashes, most due to pilot error.

Building A Life

Stationed in Orlando, Florida, in the latter war years, Phil was discharged in 1945. In 1948 he graduated from John B. Stetson University Law School and joined the firm of Rogers and Lassiter in Kissimmee. He later became partners with Lawrence Rogers and took over the business following Rogers’ death in 1960. In 1950, Phil met Jane Perrigo Connolly when the two were golfing in College Park. They were married in an outdoor wedding at Phil’s property, “Whereas” on Fish Lake, with Jane’s two daughters serving as attendants.

Phil kelley
Phil as Judge Roy Bean

Phil was a member of the Florida Bar Association, Selective Service Board, and the Judicial Nominating Committee for the 9th Judicial Circuit. He also served as Osceola County Prosecuting Attorney, Judge of the Small Claims Court, and Kissimmee City Attorney. Phil’s civic involvement extended to being a member of American Legion Post 10, First United Methodist Church, Silver Spurs Riding Club, Country Club of Orlando, and a charter member of the Kissimmee Elks Lodge 1873. During Rodeo Week, Phil became Judge Roy Bean, holding court over the Kangaroo Courts set up on the street in downtown Kissimmee. The “Judge” would throw tourists not dressed as cowboys or cowgirls into a mock jail or charged them a fine, which was donated to a local charitable project.

Described as an “old-time chivalrous” lawyer by his colleagues, Phil was also generous in his support of community groups such as United Way, Osceola County Humane Society, Osceola County Cancer Society, and others. He lived out his life at “Whereas,” passing away at home on St. Patrick’s Day, March 17, 2006, Irish to the end. A family member revealed to Osceola History that she still has many of Phil’s bow ties, including a mink one.

Written By Anza Bast