Welcome to Crestwood: Meet CHS Principal Bentley
Tue, 08/12/2025 - 3:56pm
admin
By:
Rachel Riley TPD Reporter
CRESCO - Crestwood High School is starting the new academic year with fresh leadership and a uniquely qualified, spirited new principal: Mr. Neal Bentley. Though he didn’t walk the halls of Crestwood as a student, he brings a lifetime of diverse experiences, a deep appreciation for the community, and a clear commitment to students and staff alike.
Bentley’s path to the principal's office was anything but traditional. He attended a remarkable seven colleges (yes, seven—that is not a typo) before settling into his undergraduate studies at Upper Iowa University, where he earned a degree in secondary education with an emphasis in Industrial Technology. He later completed his Master of Education in Principalship at the University of Northern Iowa.
"I took the smorgasbord approach until I found the right fit," Bentley jokes. "Cabinetry, construction, homemade root beer, traveling salesman, factory work, education, bus driving -- everything I’ve done and everyone I've interacted with have provided me some measure of insight and learning."
Born in Wisconsin and graduated High School from Central of Elkader, Iowa, Bentley moved to Northeast Iowa after marrying a local. Together, they’ve raised three children: one studying commercial aviation at the University of North Dakota, another pursuing environmental sciences at Northern Michigan University, and their youngest just entering his sophomore year of high school.
When he’s not leading a school, Bentley enjoys playing acoustic guitar and LOUDLY singing -- sometimes off-key, he admits. "I imagine my CHS students will experience that. Hopefully, some will join in," he adds.
So why Crestwood?
"I really like the size of Crestwood -- it affords our students a variety of opportunities to sample, yet not be lost as a number within a system. NE Iowa students are seen as valuable learners with good work ethics -- that for me creates tremendous opportunities as an educator." He adds, "I’ve been impressed with our dedicated staff, and am excited to join this strong network of team-oriented individuals."
Bentley brings a student-first philosophy to his role. Directed to any students reading this article, he would like to say, "I hope to guide you through your journey at Crestwood as you choose and build your version of success. Let’s recognize success does not look the same for each individual and oftentimes does not track as a straight-line graph. Some of the best learning I’ve encountered in life followed a cycle of complete and utter failure, focused relearning, repetition, practice, and eventually mastery (or at least proficiency). I wish for you an easier process, though I imagine you may experience something similar in life (to my own experiences). Don’t worry, with your dedicated work and effort, our teachers and paras will help you through your speed bumps in learning.”

