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Off the Clock: Dennis Chaltraw

By Matt Skoufalos

About 20 years ago, Dennis Chaltraw remembers leaving an insurance industry leadership conference with an important takeaway from the featured speaker. He doesn’t recollect the specific phrasing, but the takeaway was, “Regardless of how hard you work, make sure you bring balance into your life, and find a way to live outside of work.”

“There was something about this that made me realize what I was not doing,” Chaltraw said. “I had this huge briefcase of work, and would truck it home every night with the best of intention of getting it done. After 20 years of grinding it out in the insurance and finance industries, I had to find a way to push myself in other directions.”

“For people who are in high-volume, high-pressure careers, you can really enjoy what you do outside of work because your work is really stable and pretty consistent,” he said. “But once you start not doing anything, you keep not doing anything; a body at rest tends to stay at rest.”

Chaltraw reflected upon his interests. A former athlete, he began searching for opportunities to reconnect with the sports he played in his youth. He decided to start by umpiring his daughter’s softball games. That choice led Chaltraw down a path that eventually took him deep into officiating duties with USA Softball, the national governing body of softball.

“I have a tendency to throw myself into situations that I know are going to make me uncomfortable,” he said. “Officiating is a great example of putting yourself in new and challenging positions. As soon as I made the decision to take officiating seriously, an entire new world opened up, and it was something far different from my career in health care finance. I call it getting back on the field.”

Chaltraw soon learned that he’d needed to rely on more than his individual passion for the sport to do the job capably. In short order, he was introduced to the infrastructure of softball: game mechanics, case studies, positioning, and its hefty rules book. Beyond knowing and loving the sport itself, Chaltraw began to learn how to anticipate the play as an official; where to catch the optimal line of sight to best see through the play and to obtain the best possible angle to make a call. He kept up with officiating after his daughter was done with the sport, and by then, the game had its hooks in him once more.

What Chaltraw soon discovered – in addition to the effort and discipline required to become a reliable, steadily working umpire – was the significant amount of opportunity for younger people to take on the duties of officiating in organized sports. Some of his umpiring peers are in their sixties and seventies; despite their institutional knowledge, when age sets in, the physical elements of the job become much more difficult to endure. For the sport to continue to function, a new generation of officials must be identified and inducted into the system, Chaltraw said.

“We’ve got to figure out this youth movement,” Chaltraw said. “We have to drive towards youth, because there’s a big gap between people aged 30 to 50 who are not officiating. We have to circle back to the youth and plant that seed – get them back on the field.”

Chaltraw found recent success recruiting high-school athletes who had played softball previously and had no idea the amount of focus and training it took to be an official, let alone recognizing that the money they can make officiating is much better than expected. In Oregon, officials can make $50 per game to umpire; in a weekend tournament, those who hustle can net $300-$400, a nice payday for a weekend of staying close to the game they love. 

Along the way, Chaltraw said he’s also made more than his share of friendships.

“You start developing friendships with people you would have never met had it not been for getting back on the field,” he said. “For me, it has a lot to do with working with men and women who have integrity. Officials care about what they do. They care about putting a good product on the field; they care about the rules and the proper mechanics.”

After years of officiating, Chaltraw can recall some of the most challenging calls he’s had to make on the field. As a home plate umpire, he’s had to take control of more than one game when his officiating crew didn’t make an immediate call on the play or misunderstood a rule. Some of the most significant games he’s officiated have been in upper-division national championship tournaments, but regardless of its level, every game has the fire of a championship game for the players involved.

“You don’t care if it’s 10, 12, 14-year-olds,” Chaltraw said; “it’s intense, everybody’s into it, and every pitch counts. You have to be on your game.”

In those moments after play has concluded and everyone’s gone home, Chaltraw said there’s still often plenty for him to learn – from the calls he’s gotten right as much as from the mistakes he’s made.

“There’s always another perspective on it,” Chaltraw said. “Maybe you got the call right, but your positioning was wrong. The better officials always ask themselves, ‘What did I miss?’ or ‘What could I have done differently?’ ”

“When I first started, it was really about getting as many games in as you can,” he said. “You see all levels of ball and skill, you make all kinds of mistakes, and hopefully you learn from your mistakes. The speed of the game sometimes dictates what you can and can’t do. It’s better to stop and read the play than make a call on the run.”

For those interested in pursuing officiating, Chaltraw recommends they contact the local assigners for umpires in their areas as a first step. From there, they’ll begin training, in the form of remote coaching and hands-on camps at which they’ll be observed as much for their ability to receive feedback as for their ability to call a play correctly. More than anything, Chaltraw advises anyone working long hours in a day job for years on end to find something outside of the office to engage in; something they enjoy, something they can be passionate about.

“I’ve chosen officiating to help provide some balance in myself, personally,” he said. “There are entire worlds, friendships and challenges out there to be had. Find something you enjoy, put that briefcase down, and get back on the field.” •




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