Before coming to Grand Island, Dr. Dempsey was principal at Cleveland Hill High School and an assistant principal at Kenmore West High School for four years.

Previously, he had been a teacher at Gateway Youth Center, now Gateway Longview; an assistant principal for the Erie 1 BOCES Potter Road Occupational Center in West Seneca, and principal at the Erie 2 BOCES Wallace D. Ormsby Vocational Technical Center in East Aurora.

After he retired from Grand Island, he accepted the post of director of academics at Sacred Heart Academy, which he held for five years.

In 2013, he came back briefly to Grand Island as interim high school principal after the principal who succeeded him resigned to become school superintendent in Eden.

He received a special Lifetime Achievement Award in 2006 from the Grand Island Chamber of Commerce.

He was a former vice president of the Erie County School Principals Association.

Nicknamed “Moose,” he coached football at Williamsville East High School in the 1970s and 1980s and more recently at St. Joseph’s Collegiate Institute. He also coached basketball at Cardinal Dougherty High School and a variety of sports at Gateway Longview.

He played adult fast pitch softball and was a baseball and softball umpire for many years.