Bill Webster turns a negative into life-changing decision

Bill Webster umpires the Junior League Softball Little League World Series in Kirkland, Wash.

Bill Webster umpires the Junior League Softball Little League World Series in Kirkland, Wash.

District 3 Little League / Contributed photo

Bill Webster had a plan. After playing baseball and wrestling at Milford High, he thought of going to umpire school in Florida. He shrugged off that idea and athletically turned to playing rec softball. Webster enjoyed his life with wife Debbie and his two daughters. He liked working on automobiles, so he had a career. He loved to ride his motorcycle.

Then his life was turned upside down.

“I was in a bad motorcycle accident in 2004,” Webster said. “I couldn’t play softball anymore. I wanted to stay in sports. Darrin Besescheck was a friend and he said, ‘Why not try Little League.’ He invited me to the Shelton Little Fellow Classic in 2005.”

Webster began working games in District 3, which includes Shelton, Seymour, Ansonia, Derby, Beacon Falls, Naugatuck, Watertown and Oakville.

Flash forward 15 years — Webster umpired this week at the Junior League Softball Little League World Series in Kirkland (Wash.).

“It was a great experience out in Kirkland,” said Webster, who was selected to umpire at Little League Regionals in 20012, 2015 and 2018. “I love the kids. The boys, the girls, the high school kids. Baseball and softball are great games. I like to let them have fun.”

Umpiring however, is a rule-based profession.

“Games are great with the players,” he said. “The worst part is when we get questioned by coaches and parents that don’t know the game. You learn to be patient. They can’t see what you see during a play. Sometimes, you want to chirp back, but you can’t. You don’t want to set a bad example. In the end it is all about the kids.”

Webster is a senior master technician, signifying the best in his craft, for Ford Motor Company.

“The two are alike,” Webster said of getting the best out of making cars run smoothly and working games. “I love working with my guys at Ford and with fellow umpires. It is all about being prepared and then following through.”

His favorite part of umpiring?

“I guess it is the bond you build with the catchers,” Webster said. “You get a good rapport going when working behind the plate. I ask what pitchers like to throw so I can be ready for it. I’ll say does he or she throw this or that.

“My favorite story is after I asked a 12-year-old baseball catcher if his pitcher likes to throw fastballs or mostly curves. He answered and then the pitcher throws a pitch to the first batter. I said to the catcher, ‘What kind of pitch was that?’ He said: ‘A knuckle curve.’ I said: ‘Why didn’t you tell me?’ He said: ‘You didn’t ask me if he threw that one.’”


The selection process to become a World Series umpire is lengthy and rigorous. The process for selection to work a World Series begins with a recommendation from the District Administrator, within their district, to umpire in a Regional Tournament. Little League’s nine regional offices then consider all nominated umpires before selecting those who most closely meet the selection criteria.

The umpires volunteering at each Regional Tournament are then evaluated and can receive one of two recommendations: Recommend working another Regional Tournament or Recommend a World Series assignment. Once an umpire has earned a World Series recommendation, the umpire must indicate that they wish to be considered further. Individuals who meet those qualifications are then screened annually by Little League International and Regional staffs for selection to umpire in a Little League World Series tournament.

Appointment as a member of the umpiring crew for a World Series is the highest honor that Little League can bestow on a volunteer umpire. An individual can be selected for a World Series assignment once every four years.